Florida Keys Vacation Rentals, Florida Keys Home Rentals, Homes, & More

1-50 of 279 Florida Keys Rentals

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Big Pine Key Florida Vacation Rentals - Apartment
1 / 10

Big Pine Key Apartment
1 Bedroom / 2 Bathrooms / Sleeps 3

from

$120

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:3
Type:Apartment
Per night:$120
Per month:$3,600
Pets allowed:No
Internet:Yes

Lovely Furnished Apartment On A 25th Floor Of One Of The Highest Buildings In San Juan, With Marblle Floors, Facias, Indirectr Lighting Central Air Conditioned, New Kitchen With Stainless Steel Appliances Where You Can Have A Couple And A Child Sleeping Comfortably. The Two Bathrooms...

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Private Heated Pool
1 / 15

Key West Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$386

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$386 - $857
Per week:$2,699 - $5,999
Pets allowed:Yes
Internet:Yes

Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid- century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has ...

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Amazing Experience Each and Every Time!!!

“ Excellent ”
October 10, 2010
I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the outside dining area. If you are looking to rent I would highly recomend the Brass Palm Villa!
Lynne Martino, New Jersey

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1 / 37
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

AMELIA HOME - A 2 bedroom 2. 5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods...

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Emerson Enamroado Pejuan

“ Excellent ”
April 22, 2014
the house is fine , but must change the furniture of living room , are very old ., dont have iron and iron board .Opción of payed pictures
Emerson Enamorado, Honduras C.A.

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Sugarloaf Key Florida Vacation Rentals - Home
1 / 8

Sugarloaf Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 14

from

$167

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:14
Type:Home
Per night:$167 - $184
Per week:$1,167 - $1,284
Pets allowed:No
Internet:Yes

You and your family will absolutely love Bow Channel Manor! Situated on a very private 4- acre parcel on Upper Sugarloaf Key, you, your family and your friends will create wonderful memories here. It's like having your own private resort! There are 3, separate homes on this...

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Ramrod Key Florida Vacation Rentals - Home
1 / 8

Ramrod Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$100 - $117
Per week:$700 - $817
Pets allowed:Yes
Internet:Yes

The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer. This home is beautifully decorated in island style with attention...

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
2 Bedrooms / 1.5 Bathrooms / Sleeps 4

from

$60

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$60 - $77
Per week:$420 - $537
Pets allowed:No
Internet:Yes

Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation home offers views, a deep- water boating and swimming canal and a protective seawall. This home offers 2 queen- size beds and an additional sleeper sofa. A glassed- in...

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Penthouse
#1 of 2 pools with waterfall
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / Sleeps 16

Bedrooms:6
Bathrooms:7
Sleeps:16
Type:Villa
Per night:$1,143 - $2,000
Per week:$7,995 - $13,995
Pets allowed:No
Internet:Yes

Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless...

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Long Key Florida Vacation Rentals - Home
1 / 29

Long Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 9

“ Excellent ”6 Reviews

from

$243

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:9
Type:Home
Per night:$243 - $300
Per week:$1,700 - $2,100
Pets allowed:Yes
Internet:Yes

Huge Master Bedroom With View Of Beach And Large Balcony, Refrigerator And Microwave And Bar In 2nd Floor... Master Suite. Beautifull Sunrise Off You Private Balcony. First Floor Large Bedroom With Bath, Large Living Room, Dining Room, Sitting Area With Single Bed, Perfect...

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Family reunion

“ Excellent ”
August 4, 2014
We were a party of 7 and there was plenty of room for everyone. The house sets up beautifully for those wishing to take advantage of the view and use the patio. We brought our two dogs and with the gate in front we never felt they were in danger. Stayed from Saturday to Saturday which was the perfect amount of time. Plenty of good restaurants between Islamorada and Marathon which takes about 15 minutes to get to. Great charter fishing in Marathon ("Main Attraction"), both captain and mate were fantastic. Highly recommend this property if you really want to sit back, relax and enjoy The Keys the way they are meant to be.
Tom Gieseking, Orlando, Florida

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Marathon Florida Vacation Rentals - Home
1 / 27

Marathon Home
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$428

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$428 - $643
Per week:$2,995 - $4,500
Pets allowed:Yes
Internet:Yes

Escape to your own private tropical island! This Vacation Rental home combines the best of both worlds, a modern, fully furnished, waterfront shore home with all the amenities for your nights and your own private tropical island for your days. This vacation home rents from...

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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$97

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$97 - $114
Per week:$677 - $794
Pets allowed:No
Internet:Yes

From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises all the comforts of home, and so much more! The 40' dock and yard is landscaped with native foliage and offers wandering pathways throughout....

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Marathon Florida Vacation Rentals - Home
1 / 35

Marathon Home
6 Bedrooms / 5 Bathrooms / Sleeps 10

“ Excellent ”1 Review

Bedrooms:6
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,000
Per week:$5,000 - $6,500
Pets allowed:No
Internet:Yes

About 10, 000sq ft Luxurious 5 Bedrooms with Office, 5 Baths, Deep Waters Canal along with Dock Area, 4 floors, Swimming Pool, Deck at all floors, a few steps distance from the Sombrero Beach that is one of best beaches in Florida Keys, At the bottom, there is parking under...

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Fabulous home

“ Excellent ”
January 6, 2015
Our extended family rented this home for two weeks. It was every thing we expected and more. It was spacious and clean. When the coffee pot broke, we called the maintenance number and within a very short time, we had a brand new coffee pot...on Christmas Day, no less! We loved spending time in the pool, watching the iguanas, and finding "Hermie".. A hermit crab. It is such a peaceful place...a great place to relax! We would love to return some day .
Mary Smith, Eugene, Oregon

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1 / 17

Cudjoe Key Home
5 Bedrooms / 3 Bathrooms / Sleeps 14

“ Excellent ”1 Review

from

$415

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:14
Type:Home
Per night:$415 - $570
Per month:$12,450 - $17,100
Pets allowed:Yes
Internet:Yes

This 1. 6 acre gated property is great for large groups wanting space and privacy. Architecturally Designed The Main House is a two floor conch style house on stilts. It sleeps 8- 10 people, with 4 bedrooms, 2 baths, and a sofabed in the living room. Built in 1986, each room...

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Great for large families!!!! Perfect location!

“ Excellent ”
August 27, 2014
Where do I start?! This place was great for our party of 10. Everything was provided, extra towels, handmade soap, shampoo and conditioner. The kitchen had everything you needed, even extra trash bags!! The laundry area had plenty of beach towels and laundry detergent as well. The balcony was nice but my favorite was the shade and breeze you get under the house. There are hammocks and tables set out which is quite enjoyable. There are also plenty of rooms and beds to sleep everyone. We even were able to end up having individual rooms. The grill area is fully stocked, our favorite part was the large gas boiler that we could cook our lobster in without smelling up the house. The pool is great, it is in the sun all day. Plenty of things to enjoy on the property: swings, hammocks, pool and jacuzzi, and fruit trees! We will definitely be back to stay here. Kris the property manager was great and was available if you needed anything at all. I did not give it 5 stars for a few very nit picky reasons. There wasn't ac in the downstairs bath, which you never notice until you go to shower and are trying to put your clothes on but can't open the door to let air in bc there are people in the house. The pool wasn't clean when we arrived and the pool deck still had beer bottle tops laying around. I do realize that there are lots of trees around and it's impossible to keep all debri out. Besides that everything was GREAT, the owners are very nice and easy to do business with. Thanks for opening up your home it was a real treat and was just what we needed for all of our family!
Crystal K. Morgan, St. Augustine, Fl

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Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

CORAL GARDEN: A 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start...

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view from the apt
1 / 1

Key Largo Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$143

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$143
Per week:$999
Pets allowed:No
Internet:Yes

I have one week available at "ANCHORAGE RESORT AND YACHT CLUB" starting SUNDAY, Feb 15th, to SUNDAY Feb 22nd. Condo is on the 5th floor of a nice building overlooking Black Water Sound, facing West... You can sit on the large balcony and watch the beautiful sunsets or the boats...

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$79

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$79 - $84
Per week:$549 - $584
Pets allowed:No
Internet:No

Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy ride under some bridges to Pine...

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1 / 16

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$215 - $400
Per week:$1,500 - $2,800
Pets allowed:No
Internet:Yes

This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is available) Bike & scooter...

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$187

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$187 - $197
Per week:$1,307 - $1,377
Pets allowed:Yes
Internet:Yes

Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen TV. Enjoy a swim in the new,...

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SunSet Water side Tiki Hut Key Largo Cottages, A Great day of rest & relaxation
1 / 26

Key Largo Cottage
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$225 - $275
Per week:$1,575 - $1,925
Pets allowed:No
Internet:No

The Owner's Unit is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids plus plus. The main bedroom has a queen size bed, the second bedroom has a queen size loft bed and a twin bed on the ground floor. Theres also a queen size pullout sofa bed ...

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1 / 16

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$107
Per week:$747
Pets allowed:Yes
Internet:Yes

This is a beautiful 2 bedroom / 2 full bathroom home for rent in Key Largo, Florida located within a gated community. You have a gorgeous ocean front property with beach access. If you have a boat this property is just for you, you have water access to anchor boat with water...

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Marathon Florida Vacation Rentals - Townhouse
1 / 34

Marathon Townhouse
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$193

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Townhouse
Per night:$193
Per week:$1,350
Pets allowed:No
Internet:Yes

Truly a PARADISE..! Guests will surely love this beautiful marina town home overlooking the open Gulf waters. 3BR/2. 5BA in fully gated Indigo Reef Resort in Marathon at Mile Marker 53, in heart of the Florida Keys . The furniture and interior has all been upgraded from the "standard"...

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Marathon,FL.

“ Excellent ”
January 16, 2015
This townhouse was great. John the owner made sure everything was to our satisfaction. A very quite development and the people were very nice.
Bruce Hoffman, East Greenwich NJ USA

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$77 - $84
Per week:$537 - $584
Pets allowed:No
Internet:Yes

Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for privacy and lots of yard space ...

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Marathon Florida Vacation Rentals - Villa
1 / 22

Marathon Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$658

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Villa
Per night:$658 - $1,158
Per week:$4,600 - $8,100
Pets allowed:Yes
Internet:Yes

Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5. 5 bath home with luxury in every detail and design. Sleeps up to 12 guests. Features include cathedral ceilings, marble, stainless steel and mahogany finishes,...

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Great Vacation with Family

“ Excellent ”
December 1, 2014
We stayed at this house with our extended family. I was very apprehensive but it wound up being wonderful. Beautiful location, secluded from the world. Tons of space for us to all move about, access to cottage amenities, quick drive to Marathon and Islamorada. Lovely pool and hot tub just for us. Dock area is too shallow to really swim off of it, but there is a beach entry by the cottages. Will definitely return. Only complaint is the house is worn from the many people who visit this property. I saw this as confirmation that it is well used and popular, but the bathrooms could use a coat of paint. If that is your only worry, you are truly enjoying paradise. Thank you Conch Key for all your help and recommendations. Spot on for them all!!!
Nina Felt, Dallas, TX USA

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Marathon Florida Vacation Rentals - Home
1 / 9

Marathon Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”5 Reviews

from

$265

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$265
Per week:$1,850
Pets allowed:Yes
Internet:Yes

The property is located at the end of the block. It has an open garage that two full size trucks could park in. It has 4 bedrooms, 2 1/2 bathrooms, if you have a boat we've got you covered with approx 200 feet of canal. Dock facilities include fresh water, electricity, and a cutting...

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good place with great backyard

“ Excellent ”
January 4, 2014
The house was a bit small for 8 people, If they had gone for a smaller furniture in the living/dining room,the room would have seemed bigger. But the Backyard and the view compensated for any flaws inside the house. It was just so beautiful and relaxing.
lavanya srinath, HIghtstown, New Jersey

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1 / 26

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

KEY WEST FOUND – A striking 2 bedroom, 2. 5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features...

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Wonderful

“ Excellent ”
October 16, 2014
Perfect location...reasonable rent
Judy Kolbe, Okauchee,Wi usa

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Marathon Florida Vacation Rentals - Home
1 / 20

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”17 Reviews

from

$193

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$193 - $343
Per week:$1,349 - $2,399
Pets allowed:No
Internet:Yes

New home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, pool home - perfect for three couples or a family. As close as you can get to the 7- mile bridge for great sunsets and quick boating access for bridge fishing or the oceanside. Fabulous views of the open water...

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Great location, wonderful hosts

“ Excellent ”
October 12, 2014
We stayed here a week during Sept. 2014. The house was clean and the location was perfect for our needs. Easy drive down to Key West, and close to the Seven Mile bridge. We enjoyed having the bikes for rides to restaurants and site seeing. The small pool was really just right for our needs. The residence keepers did a good job of repairing our bike tire and answering questions. We did have some ants visit us, and I understand this is a typical problem for residences in the Keys. We would recommend this place for anyone wanting to get away for a peaceful stay. Places we recommend to visit are Robbie's Dock(Islamorada), Seadog fishing boat, the No Name Pub down on Big Pine Key(go there just before sunset and see lots of Key deer), Key West(Hemingway House and Mallory Square), snorkeling the Sombrero reef, and a stop by the World Wide Sportsman store on Islamorada. We highly recommend!
Bill Hocker, Bradenton, FL

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Marathon Florida Vacation Rentals - Home
1 / 32

Marathon Home
8 Bedrooms / 6 Bathrooms / Sleeps 20

from

$757

/ night

Email Owner
Bedrooms:8
Bathrooms:6
Sleeps:20
Type:Home
Per night:$757 - $1,085
Per week:$5,295 - $7,595
Pets allowed:Yes
Internet:Yes

WHAT IS UNIQUE ABOUT THIS VACATION HOME? This home offers a great option for multi- family vacationing by providing two 4- bedroom homes side- by- side. This gives you 2 kitchens, 2 pools, 2 100' long deep water docks, sandy shoreline, teak lounge chairs, 2 gas grills, 6 kayaks,...

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Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

EASY LIVIN' - - The name says it all! This lovely private home with pool is located in a secluded cul- de- sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. ...

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Beach
1 / 16

Key Largo Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”36 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$175 - $225
Per month:$5,250 - $6,750
Pets allowed:Yes
Internet:Yes

Cozy cottage with sandy beach located in Key Largo on an acre of tropical waterfront. The children will enjoy playing on the beach with toys provided. Or fish from the 100ft dock with fishing equipment provided. Bring a boat and have FREE dockage. Lounge in the hammock under the palm...

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True piece of paradise

“ Excellent ”
December 16, 2014
We had an amazing time, beautiful sunsets we cant wait to go back, perfect location, you can fish from the dock (we were very lucky), clean and cozy
Ochun Leti, Americus, GA

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Big Torch Key Florida Vacation Rentals - Home
1 / 18

Big Torch Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”6 Reviews

from

$285

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$285
Per week:$2,000
Pets allowed:Yes
Internet:Yes

Big Torch Key is reminiscent of the Florida Keys 40 years ago, seclusion and peace invade your senses immediately, sunset views that will take your breath away. Torchview has an open floor plan (kitchen/living room/dining room) with a huge master suite(king bed)and two other bedrooms...

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Awesome Birthday vacation!

“ Excellent ”
July 14, 2014
Our family decided to rent Torchview after falling in love with the home from a distance. We had stayed at a neighboring cottage the year before and were looking for a larger rental. Knowing we would need more room for more family members who would be joiing us, we made or reservations. Upon our return to Summerland we settled in comfortably with our two teenage children, our 3 dogs, and our inlaws. (no pun intended with the order). The home is located on over an acre of land, close to the Deer Key preserve. The property sits on a beautifully landscaped gated oasis, comfortably appointed, and nicely kept. We thoroughly enjoyed seeing Key Deer in our garden, the enormous amount of tropical fish right under the dock, with easy access to our boat for intercoastal and big water fishing. The Florida Sunkist Sunsets were breathtaking and spectacularly sweet. We celebrated my birthday in Key West which is only 30+ minutes from the house. We will definitely return next year! Keep in mind that if you have a hard time climbing stairs this location may present some difficulties. We also loved the fact that we could bring our furry children to enjoy the vacation with the family! Thank you for the privilege of enjoying your beatiful home!
Elizabeth Bigles-Christensen, Stuart, Florida

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Little Torch Key Florida Vacation Rentals - Home
1 / 8

Little Torch Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$408

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$408 - $429
Per week:$2,850 - $3,000
Pets allowed:No
Internet:Yes

This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house is painted in bright tropical colors to give you that that old island feel. This spacious 2, 000 square foot house has plenty of room to spread out. On one side are...

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Super Holiday

“ Excellent ”
December 30, 2014
Can't say enough good things about the stay. The house was even better than advertised.
warren compton, Frenchtown, NJ

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 10

from

$180

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$180 - $184
Per week:$1,260 - $1,284
Pets allowed:No
Internet:Yes

A get away to "Our Island Thing" will be unforgettable vacation for everyone. Huge 1, 900 square- foot house with lots of room for the whole family and kids. Four bedrooms and 2 bathrooms. 2 level concrete home is roomy and airy. 2nd floor has a huge kitchen, living and dining area,...

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Marathon Florida Vacation Rentals - Home
1 / 8

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

The Sombrero Pool Home A great Vacation spot! Pool, Spa, Dockage and only a 1/2 Mile from Sombrero Beach! This 3 bedroom, 3 bath home has a refreshing feel to it the moment you walk in the door. Full of color to make your vacation days start and end on a happy note. The ...

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Marathon pool home

“ Excellent ”
July 1, 2013
Beautiful home with a great location. Good ocean access. Inside of home was fairly well kept the only disappointment was the 3rd bedroom located on the bottom floor isolated from the rest of the home. The pool was great ...dock was perfect. All things considered it was a good vacation home!
susan atwell, Florida USA

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1 / 28

Key Largo Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”7 Reviews

from

$210

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$210 - $325
Per week:$1,200 - $1,550
Pets allowed:Yes
Internet:Yes

Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home has three wonderfully decorated, clean and cozy bedrooms. Two and 1/2 comfortable and clean bathrooms. Full kitchen is stocked with all necessary cookware, ...

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Excellent location

“ Excellent ”
June 2, 2014
very warm and comfortable home, with a large dock and direct ocean and bay access. walked over to the Old Tavernier Restaurant across the street nearly every evening for great dinner and drinks.
GEORGE DAGNESSES, Miami,Florida

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Cudjoe Key Florida Vacation Rentals - Home
1 / 6

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$160

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$160
Per week:$1,120
Pets allowed:No
Internet:No

This beautiful, vacation home is tropical, bright and comfortable. You'll wish it was your own! Kitchen is fully equipped with all the luxuries of home (and more! ). Tiki Hut and hammock dockside, overlook a great deepwater boating and swimming canal and 50' seawall. Enjoy...

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View from the balcony
1 / 16

Key Largo Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$400

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$400
Per week:$995 - $2,195
Pets allowed:Yes
Internet:Yes

2 bedroom, 2 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2013. It has dockage for boats up to 50 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from the patio. We provide a golf cart, Kayaks, fishing equipment,...

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Awesome stay in Key Largo.

“ Excellent ”
August 8, 2014
My family's stay in this condo in Key Largo perfect. The view was incredible. I'm giving it a full 5 stars because of the wonderful view and the relaxed atmosphere. Loved having access to full kitchen and laundry facilities. Everything was in good repair and working order.
Starla Yount, owenton, kentucky

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1 / 10
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Escape to Islamorada and enjoy this beautifully updated 2 bedroom / 2 bath townhouse located in Executive Bay Club a bay front property. This is a private gated community with 24 hour security. The property features 2 tennis courts, a full size pool with bay views, private beach,...

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Very Satisfied

“ Excellent ”
April 2, 2013
The property is in excellent condition. It was a pleasure staying at Executive Bay Club. We were fortunate to have good weather, the pool is very nice, as well as the beach and dock facilities . WE WILL BE BACK !
Fred Lipp, Highland Hts. Ohio

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Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$234

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$234 - $250
Per week:$1,634 - $1,750
Pets allowed:Yes
Internet:Yes

Gorgeous luxury open oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bath home is just perfect for large families and big boats. Over 2, 500 square feet of living space with lots of room for everyone to spread out. The kitchen has plenty of room for everyone to ...

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1 / 23

Key Largo Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$275

/ night

Email Owner
Bedrooms:5
Bathrooms:3.5
Sleeps:12
Type:Home
Per night:$275 - $475
Per week:$1,700 - $2,250
Pets allowed:Yes
Internet:Yes

Escape to your own private paradise nestled in one of the most picturesque bay coves in all of Key Largo within Black Water Sound. Enjoy fishing, snorkeling, scuba diving, water skiing, or kayaking from your own pier and dock. Bring your boat and launch away into the mysteries...

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Great For A Large Family

“ Excellent ”
July 24, 2014
We stayed with my extended family (11 of us in all including 3 kids) and this home accommodated us all. The view from the dock is amazing. Beautiful in the morning and gorgeous sunsets at night. We spent more time on the deck than in the house. It was clean with lots of living space. We loved having a full kitchen with everything we needed to cook with. The laundry room is also a plus for a long stay. Close to everything including a Winn-Dixie and Publix just down the road.
Emily Jarrett, Vero Beach, FL

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1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $160
Per week:$1,050 - $1,120
Pets allowed:No
Internet:No

Relax and enjoy this light and tropical, like- new vacation home with a private heated swimming pool. Step onto the large open porch and soak in the warm Island breezes while overlooking the sweeping canal views and pool. Concrete dock, shore power and fish cleaning station are ...

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Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$94 - $104
Per week:$654 - $724
Pets allowed:Yes
Internet:Yes

This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for ...

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Living Room
1 / 1

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$259

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$259
Per week:$1,813
Pets allowed:No
Internet:Yes

Decorator furnished two bedroom, two full bath condo in Key West, Florida. Only a five minute drive to Key West's largest beach - Smather's Beach. Full kitchen, three flat screen TV's, outside porch overlooking the beautiful pool and jacuzzi area on property, and one covered...

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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$84 - $92
Per week:$584 - $642
Pets allowed:Yes
Internet:Yes

Everything about this wonderful 2 bed/2 bath home is exceptional. Located just 23 miles from Key West to explore all the great activities the southernmost city has to offer. The home is decorated in tropical island style with soothing colors by one of our famous local artists....

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Key Colony Beach Florida Vacation Rentals - Townhouse
1 / 9

Key Colony Beach Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

An Oceanfront Town Home in Key Colony Beach with Beach, Pool & Fishing Pier! 3 Bedroom, 3 Bath town house with 2200 square feet of oceanfront living! Gorgeous views from the living, dining, kitchen and master bedroom. When you step into the main living level your first...

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Beach Life at it's Best!

“ Excellent ”
January 12, 2015
My wife rented this place so I had no idea of what to expect. When we checked in I couldn't believe that I was staying there! Pretty awesome place! Nice big 2-car deep garage underneath, & the upstairs accomodations were like being at home. Pool was 4 or 5 steps down from our living room. We had 3 adjacent apartments, #6, #7 & #8. Just a couple small complaints. The one we were in (#7) had a modem problem, kept going on & off, but we didn't tell anybody about it, just kept rebooting the thing. If I had to make one complaint it'd be that they should do regular walk-throughs to check things out as ours needed new fluorescent bulbs in the garage, but again we didn't make any complaints, just dealt with it. Also, I noticed that every single sliding door latch on the side/stationary doors was broken so that those doors really wouldn't lock., just the middle latch worked between the 2 doors that you always travel through. I'm surprised because in the case of a big storm or hurricane the side doors could possibly be ajar & let some rain/water in if it was blowing sideways in the right direction. Other than that it couldn't have been nicer! We would/probably will stay there again. Oh yeah, one more thing, the water to the toilet on the main floor sang without any particular pattern. At first I thought it was just when you ran the water in that bathroom, but sometimes it would just start making its noise without any water having been run. Other than these few small things everything was great.
Bob Szczypinski, Williamsburg, Va.

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1 / 28

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around...

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Key West Get Away

“ Excellent ”
October 20, 2014
We could not have picked a better place to stay. Within walking distance to the beach and all locations down on Duval. Very clan location great for two couples. Look forward to booking this location again for next years trip.
Mike Moore, Germantown Ohio

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1 / 23

Islamorada Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$150 - $250
Per week:$980 - $1,225
Pets allowed:No
Internet:Yes

Enjoy spectacular water views from the private petite beach, large TIKI hut and boat dock at the end of the community, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private ...

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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 5

from

$74

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:5
Type:Home
Per night:$74 - $84
Per week:$514 - $584
Pets allowed:No
Internet:Yes

Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 23, close to Key West and Marathon for great day trips around the islands. This spacious 3 bedroom, 2 bathroom ground level home is cozy and comfortable. Extra large screened porch overlooks...

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1 / 7

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 10

from

$400

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:10
Type:Home
Per night:$400
Per week:$2,000
Pets allowed:No
Internet:Yes

Gorgeous views in this recently remodeled elegant home. Features 2/2 upstairs and 2/1 downstairs available for rent also. Swim, fish or go boating from your private dock and/beach. Once you visit you won't wan to leave. All the comforts of home are provided. Visit for a vacation...

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1 / 21

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$513

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$513
Per week:$3,590
Pets allowed:No
Internet:Yes

CASA ROSA is a classic four bedroom, four bath "eyebrow" style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large living room and dining room with a kitchen that overlooks your own...

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Summerland Key Florida Vacation Rentals - Home
1 / 7

Summerland Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$187

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$187 - $197
Per week:$1,307 - $1,377
Pets allowed:No
Internet:No

Looking for that perfect vacation spot in the Keys? This is the one. Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42” Flat screen Sony hi- def TV with surround sound makes...

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Florida Keys Travel Tips

The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Made up of Key Largo, Islamorada, Marathon, Key West, and Big Pine Key and the lower keys, these islands have plenty of family-friendly activities. The best way to visit this beautiful area is by choosing to stay in vacation rentals by owner. Florida Keys tourists can choose from a variety of different sized properties designed to make your time in the Keys comfortable and memorable. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price. Your entire family will love exploring the islands and coming home to a private, spacious home or condo.
Beaches and Parks
While staying in one of the area's beautiful vacation rentals, Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.
Things to Do
The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Key West, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.
Local History
While staying in one of the area's many vacation rentals, Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.
Fun With Kids
While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Florida Keys rental homes are a much better choice than hotels, because families will have a cozy home base to return to after a day of sightseeing. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
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