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1 / 8

Marathon Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

(8)“ Excellent ”8 Reviews

from

$160

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$160 - $178
Per week:$1,120 - $1,243
Pets allowed:No
Internet:Yes

This deluxe two bedroom ocean view condo is located on Key Colony Beach, a small island paradise in Marathon in the heart of the Florida Keys. This unit is on the top floor of a three story building, with elevator. There are two screened sliding glass doors- one in the master bedroom...

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Great Location, Great Condo!!!!

“ Excellent ”
April 5, 2015
We truly enjoyed every minute of this beautiful condo in Key Colony Beach for the month of March, 2015. From the decor to the amazing views from the balcony, we were so happy with all the amenities. The kitchen was well equipped with everything we needed from baking pans to silverware to steak knives to serving utensils which made it very easy to prepare and enjoy meals in our "home away from home". The views from the balcony were outstanding, and we enjoyed many hours just relaxing there, and not feeling the need to rush off to do much else. My husband enjoyed fishing off the private pier with the fishing gear provided by the owners, Paula & Dave, while I enjoyed the 3 mile walk around the island in the morning and the water aerobics class. It was a wonderful place to lay back and enjoy the sunshine and warm temps while our hometown was still getting hit with snow storms. In our travels north and south in the Keys during our stay, we found Key Colony Beach to be the best location of all. We would highly recommend this rental for a truly enjoyable stay. Key Colony Beach is truly paradise!
Debbie Chimenti Sciamanda, Erie, PA USA

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Key Largo Florida Vacation Rentals - Home
1 / 45

Key Largo Home
6 Bedrooms / 4.5 Bathrooms / Sleeps 16
Home / 6 Bedrooms / Sleeps 16

(2)“ Excellent ”2 Reviews

Bedrooms:6
Bathrooms:4.5
Sleeps:16
Type:Home
Per night:$1,043
Per week:$7,300
Pets allowed:Yes
Internet:Yes

'Shadow Point' estate offers an exclusive retreat for vacationers desiring an intimate and private setting. This vacation rental is perfect for boaters, kayakers, canoers, divers and fishermen and can comfortably accommodate family retreats, workshops, weddings, and film shoots....

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Wonderful Visit!

“ Excellent ”
August 12, 2014
We loved the 1920's home, period furniture and all of the art displayed on the walls. It was like stepping back in time and felt very much like a family home. With two houses, we had space for all the adults in one and all the teens were in the smaller house, giving everyone a space for hanging out. Plus, being on two acres felt very private! Having the kayaks, paddle boards and snorkels was one of the best features--we kayaked every morning, followed by sun salutations (yoga) on the beach, and then snorkeling a few times very day. The house was well equipped, linens, towels, shampoo, blender and coffee pot all ready for use, although in August one of the AC units struggled to cool the room. The water is tea colored and visibility varied with the weather. Most of the water was shallow with lots of sea grass, but in the lagoon in front of the castle there are coral banks with lobsters (lots) and many more fish. We also saw sharks in the deep water and a sea turtle there. Being so close to Pennekamp park was great too, and we took a tour out in the Atlantic for a much better selection of coral, sea fans, parrot fish, and various angels. We will definitely go back!
Tamsen Valoir, HOUSTON

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Marathon Florida Vacation Rentals - Townhouse
1 / 10

Marathon Townhouse
3 Bedrooms / 2.5 Bathrooms / Sleeps 8
Townhouse / 3 Bedrooms / Sleeps 8

(13)“ Excellent ”13 Reviews

from

$203

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Townhouse
Per night:$203 - $357
Per week:$1,420 - $2,495
Pets allowed:Yes
Internet:Yes

Spacious and like new 3 BR 2. 5 BA homes in Marathon, Florida Keys most prestigious resorts, "INDIGO REEF Marina Resort Florida Keys" ~ Magnificent views from this home and 30 feet of docking plus accommodations to 6- 8 in total. Guests to Indigo Reef enjoy this private gated...

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Nice Condo-just wish beach was closer

“ Excellent ”
March 7, 2015
we were very happy with the cleanliness and comfort of the unit we rented. Having 3 bedrooms enabled us to let our grandson have his own room instead of needing to share with his parents or use a sofa sleeper. We rented Unit 38 and it was a very short walk to the pool...pretty much right out the front door. We did not make use of the docking as we had no boat but we did enjoy walking along said docks.Only wish would be for a closer beach and a better way to launch kayaks...really rather steep to try to do so off the docks and there is not any good walk-in access on the property. This is the reason I gave it 4 instead of 5 stars. The unit itself would rate 5 stars
Dianne Biscoe, Mukwonago WI

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Sunset at PirateHead Cove
1 / 29

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(8)“ Excellent ”8 Reviews

from

$249

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$249 - $349
Per week:$1,743
Pets allowed:No
Internet:Yes

Ahoy! PirateHead Cove, your affordable vacation dream- come- true is now taking bookings for 2015! Please check the calendar on this site for availability. We do not take rentals of less than 7 nights unless it is between 2 already booked weeks, and ONLY if it shows as available...

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Water front Key West

“ Excellent ”
December 18, 2014
Cozy home, well supplied, welcoming and engaging owners with lots of sunshine. Tucked in a quiet neighborhood on Stock Island. Great vacation.
Patricia Dubberke, Minnesota

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Marathon Florida Vacation Rentals - Home
1 / 20

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(6)“ Excellent ”6 Reviews

from

$243

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$243 - $429
Per week:$1,699 - $2,999
Pets allowed:Yes
Internet:Yes

Relax and enjoy your vacation with a specatacular waterfront view - look out over a crystal clear lagoon out onto the Gulf of Mexico. This full duplex Waterfront Home with 75' of deepwater dockage, 4 Bedrooms and 4 Baths is great for large groups looking for a quiet place to relax,...

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Great getaway w friends

“ Excellent ”
April 14, 2015
We were 4 couples that thoroughly enjoyed the property. The view was soothing and spectacular w daily turtle sightings.
Stephanie Fox, Lumberton nj

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1 / 23

Islamorada Home
5 Bedrooms / 6.5 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$484

/ night

Email Owner
Bedrooms:5
Bathrooms:6.5
Sleeps:12
Type:Home
Per night:$484 - $550
Per week:$3,384 - $3,850
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: 180 degree ocean views are yours from almost every room in this magnificent ocean front home. This home has over 5962 (not a typo) square feet of living area with 5 bedrooms, 6 and one half baths, and two full kitchens! This home comfortably sleeps 10 in...

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Islamorada Florida Vacation Rentals - Home
1 / 22

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people...

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Key Largo Florida Vacation Rentals - Home
1 / 22

Key Largo Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$175
Per week:$1,225
Pets allowed:Yes
Internet:Yes

3 bedroom, 2 bathroom vacation home. Waterfront property located Bayside in Key Largo at mile marker 105. 60 foot private dock –Watch the Manatees from the dock of the property. Just a few homes away from direct access to the Florida Bay and around the corner from Adams Cut, which...

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Islamorada Florida Vacation Rentals - Home
1 / 7

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$329

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$329 - $429
Per week:$2,300 - $3,000
Pets allowed:No
Internet:No

Enjoy a beautiful solar heated pool with Jacuzzi on the premises. You also will have access to a private homeowner's sandy beach to swim and enjoy sunsets on the next street over. Come to paradise and enjoy this fabulous Islamorada bayside canal front 3/2. Located in a quiet neighborhood...

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Beautiful and Friendly

“ Excellent ”
January 22, 2014
This house was perfect. Great location, private beach, very clean, had everything you needed. Mark is very friendly and helpful. Can't wait to visit again:)
Kelly Seitzer Gee, Ocean city, md

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Islamorada Florida Vacation Rentals - Home
1 / 19

Islamorada Home
1 Bedroom / 1.5 Bathrooms / Sleeps 3
Home / 1 Bedroom / Sleeps 3

from

$149

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:3
Type:Home
Per night:$149 - $177
Per week:$1,040 - $1,235
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 7 NIGHTS: You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who ...

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Marathon Florida Vacation Rentals - Home
1 / 9

Marathon Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(7)“ Excellent ”7 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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Outstanding home

“ Excellent ”
March 26, 2015
This is a first class property to stay in with a larger family! When we arrived and opened the front door the first thing out of everyone's mouth was WOW!! The down stairs is very open with very modern appliances. All of the bed rooms are located upstairs which consisted of a King in the master, a Queen and 2 rooms with doubles. 2 full baths upstairs ans a 1/2 bath down stairs. The TV looked a little dated but we weren't there to watch TV so it didn't bother us at all. Although the pictures showed grass in the back yard, it was all gravel, again, not a big deal to us what so ever. There was plenty of space to tie up both of our boats. There are some pilings for tying up to that accommodated our small boat (14 foot) and plenty of sea wall to tie our larger boat (27 foot) where the davits used to be. If you have large fenders, its not an issue at all. The deck provided us an excellent place to enjoy morning coffee as well as evening beverages as well. I would highly recommend this house to anybody with 6-8 people in there group. A couple of very minor negatives...the deck does need a little attention as there are some screw heads starting to come up and the water pressure in the master shower isnt the greatest in the world. Very minor issues in my book
Paul Gallup, Orange Park FL

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Key West Florida Vacation Rentals - Townhouse
1 / 11

Key West Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(14)“ Excellent ”14 Reviews

from

$258

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Townhouse
Per night:$258
Per week:$1,800
Pets allowed:No
Internet:Yes

This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered...

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Beautiful Escape in Truman Annex!

“ Excellent ”
January 17, 2015
This is a beautiful place in the heart of Truman Annex. Just 2 blocks from Duval so your close to everything, but far enough away if you prefer some quiet time. Very Relaxing Pool is a definite plus! The place does look like it the pictures if anything nicer. We loved our stay! We will stay there again! The Owners are just wonderful. This was our first time visiting Key West and We couldn't have picked a better place to stay. Thru the Week My Husband kept saying "Good Job finding this place its Great"! I can honestly say you wont be disappointed! Great Place to Vacation!
deb strieter, Unionville, Mi USA

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Marathon Florida Vacation Rentals - Townhouse
1 / 19

Marathon Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 7
Townhouse / 3 Bedrooms / Sleeps 7

(5)“ Excellent ”5 Reviews

from

$172

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Townhouse
Per night:$172 - $322
Per week:$1,200 - $2,250
Pets allowed:No
Internet:Yes

This 3 bedroom, 3 bath, half duplex townhouse offers all you need for a great vacation. Stunning open water views of the Gulf of Mexico, beautiful sunsets, your own private pool and cut in boat slip with lift. Great views from the living area and master bedroom. The ground level...

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fantastic experience at 7 mile bridge

“ Excellent ”
April 5, 2015
this property is better than described. The location is perfect. Day trips in either direction is easy and within an hour youre there. House is neat and up to date. Bicycles and kyak are definitely a plus.Biking on seven mile bridge Is neat. Marathon is not your average tourist town. Very laid back and as normal as anywhere. The views at sunset are awesome. pool is a great retreat after a day trip. used the grill to cook fish caught. special thanks to Kitty Whalton at vacation rentals, she was right on with information on property and surrounding things to do. GREAT TRIP !!!!!!!!!! thank you.
Wayne Brosemer, Utica, NY USA

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Marathon Florida Vacation Rentals - Home
1 / 12

Marathon Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$715

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

This luxurious executive home is located in the Heart of the Florida Keys on Yacht Harbor Island in Marathon. Come and enjoy the new private pool surrounded by paver decking and two tiki huts for plenty of shade. The 120' of deep water dockage is perfect for your boat, jet skis, ...

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Key Colony Oasis

“ Excellent ”
March 30, 2015
Paulette, the Bldg. mgr. made everything so easy. We absolutely loved the house. So spacious. Great layout for entertaining. Great ocean & Gulf access with our rental boat. Loved playing with the manatees at the dock. Loved the little Key Colony community. Great area to walk, or, bike ride.
Ina Hughes, St. Louis, Mo.

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Islamorada Florida Vacation Rentals - Condo
1 / 25

Islamorada Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$179

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$179 - $257
Per week:$1,250 - $1,795
Pets allowed:No
Internet:Yes

MINIMUM STAY 7 NIGHTS, SATURDAY TO SATURDAY RENTAL ONLY BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina....

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$107 - $157
Per week:$747 - $1,097
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, ...

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Islamorada Florida Vacation Rentals - Home
1 / 21

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$315

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$315 - $372
Per week:$2,200 - $2,600
Pets allowed:Yes
Internet:Yes

Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnished in rattan and decorated with a tropical flair. Coconut palms,...

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Paradise in Islmorada

“ Excellent ”
July 6, 2010
Excellent location with a great view of the Canal. The Pool was the right size for our family and the Outside bar was Outstanding. The deck and dock were perfect for my 25' boat with ample room for my Grandson to fish for snapper. The Upstairs kitchen and living area with the high ceilings was fantastic. The downstairs bedroom was also great. The whole experience was truly enjoyable for my family.
BILL WHITE, STUART FLORIDA USA

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Marathon Florida Vacation Rentals - Home
1 / 23

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$172

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$172 - $229
Per week:$1,200 - $1,600
Pets allowed:No
Internet:Yes

Seven night minimum. Canal front home on the Atlantic Ocean side of Marathon. This stilted home has two bedrooms, 2 baths, and comfortably furnished for your stay. Enjoy the breezes and gaze at the stars. There is 30 feet of dockage for your boat, Located in a quiet neighborhood....

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Key Largo Florida Vacation Rentals - Home
1 / 17

Key Largo Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$120

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$120 - $140
Per week:$840 - $980
Pets allowed:Yes
Internet:Yes

Beautiful Key Largo home resting on a private canal with access to Black Water Sound in the presigious community of Stilwright Point. Beautifully decorated with everything you will need for the vacation of a lifetime. Three comfortabel bed rooms with the master enjoying the entire...

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EXTERIOR OF HOUSE
1 / 9

Islamorada Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(5)“ Excellent ”5 Reviews

from

$300

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:Yes

This beautiful 4 bedroom/ 4 bathroom home has a 70' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2...

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Islamorada, 110 El Capitan '15 Stay

“ Excellent ”
April 5, 2015
House was great, clean and well maintained. Neighborhood is very nice, I've stay there before. Location is perfect with close proximity to fishing marinas (Robbie's and Bud & Mary's) as well good dining locations (Islamorada Fish Company, Ma's Fish House, Chef Michael's and Lazy Days). Twenty minutes to Marathon. Will consider staying again in the future.
Dow Carter, Libertyville, IL

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$133

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$133 - $158
Per week:$931 - $1,103
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...

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Marathon Florida Vacation Rentals - Home
1 / 11

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$300 - $358
Per week:$2,100 - $2,500
Pets allowed:No
Internet:Yes

Get away from the outside world at this lovely hide- away that includes two bedrooms and two bathrooms, a pull- out sofa with panoramic view of the Gulf of Mexico from every room. We've made an effort to provide the things that what will make your stay comfortable, fun and enjoyable....

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Wonderful Place

“ Excellent ”
November 3, 2014
My husband and I just finished our second stay at Gerry's Place and I'm sure it won't be our last. It has everything you need to have a great Florida Keys experience! Hope to be back again next Fall!
Vicky Rorrer, Ohio

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1 / 8

Islamorada Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 8
Townhouse / 2 Bedrooms / Sleeps 8

(2)“ Excellent ”2 Reviews

from

$315

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:8
Type:Townhouse
Per night:$315
Per week:$2,200
Pets allowed:No
Internet:No

Come enjoy a slice of paradise in this beautiful ocean front property settled in a private, gated and lushly landscaped community. Take it all in, from the breathtaking ocean views, to the serene swimming pool, it's like a tropical dream come true. In addition to the pool this...

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Fun, family vacation in the FL Keys

“ Excellent ”
April 5, 2015
We enjoyed a fun, warm week steps away from the Anglers Reef pool with our two kids ages, 4 and 6. About 1 hr 45 min drive from. Miami, depending on traffic. Upon arrival, the house was clean and well set-up. Good sized kitchen and downstairs living space (including 1/2 bath) and spacious 2 upstairs bedrooms each with their own bath. The upstairs washing machine was much appreciated and used hard! A few items to add to help with families with small kids include a step stool or two so kids can reach the sinks to wash hands and brush teeth without assistance and more melamine plates and cups which make dining al fresco (in particular) more feasible with little ones. Also would have loved to have access to kids' sized life vests to enjoy the owner's kayak. We did not end up using the kayak this trip. We enjoyed making most of our own meals in the kitchen and could have used a few more items to make that process a bit smoother, but great news was the blender worked well for frozen drinks :) Location is great and a mile or two down Overseas Highway from Theater of the Sea (a must see marine mammal park for families) and almost across the street from Smugglers Cove where we took a Family Fun Boat Tour, another great family experience. Note that the house sits close to the entry gate and is therefore not too far from the roadway. Not a safety issue due to the gated community but you are able to hear the Overseas Highway traffic. Two thumbs up for a fun family vacation! We were all sad to pack up and come back to cold PA.
Lori Hood Sanders, Garnet Valley, PA

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$110

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$110 - $164
Per week:$770 - $1,144
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on ...

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Key Largo Florida Vacation Rentals - Home
1 / 17

Key Largo Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

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

Come enjoy this family friendly house. There are 3 bedrooms and 2 bathrooms upstairs and a separate 1 bedroom 1 bathroom and kitchen downstairs. There is a balcony off of the living room where you can sit and have your morning coffee as you watch the ocean. The house is completely...

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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH - You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. ...

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Key West Florida Vacation Rentals - Condo
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(8)“ Excellent ”8 Reviews

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

TAKE 25% OFF: - - Stay April 4- 6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1, 025. - - Stay April 11- 14 (3 nights) and pay a reduced rate of $1, 125 for all three nights instead of $1, 500. - - Note, taxes and fees will be added to all rates....

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Better than ice cream!

“ Excellent ”
May 16, 2014
I spend a week in Key west this time every year with my cousins, in celebration of one's birthday. We have a goal to always find a place to stay that allows us the most time all together. We have found some nice places on VRBO but this welcoming home captured our hearts the moment we entered. The attention to detail was impeccable. The view was gorgeous. The beds were cozy. Linens comparable to a four star hotel. Peaceful and serene. All the wants taken care of. We fell in love, so will everyone.
April Rubenstrunk, New York

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Tavernier Florida Vacation Rentals - Home
1 / 15

Tavernier Home
5 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$167

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$167 - $217
Per week:$1,166 - $1,516
Pets allowed:Yes
Internet:Yes

A beautiful, relaxing 5 bedroom home at Harry Harris Beach (mile marker 92. 5). Enjoy the heated in- ground pool and attached spa in the enclosed back yard. Entertain from the poolside bar and grill while friends and family chat under the tiki hut. Walk across the street...

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Islamorada Florida Vacation Rentals - Cottage
1 / 24

Islamorada Cottage
2 Bedrooms / 1 Bathroom / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$150
Per week:$1,050
Pets allowed:Yes
Internet:Yes

Newly remodeled mobile home cottage is more than you've imagined so far. Enjoy the bright open living area with panoramic horizon view from the kitchen/living room. Open the 2 sets of French Doors to bring the outside, in. Sit on the wrap around deck to watch the Sun Rise out of ...

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Tavernier Florida Vacation Rentals - Home
1 / 30

Tavernier Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$225 - $259
Per week:$1,575 - $1,809
Pets allowed:No
Internet:No

MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious and surrounded by...

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Key Largo Florida Vacation Rentals - Home
1 / 28

Key Largo Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$332

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$332 - $425
Per week:$2,322 - $2,975
Pets allowed:Yes
Internet:No

MINIMUM STAY: 1 MONTH Looking for a spacious ocean front home but don't need a mansion? The upper two floors of this home offer an elevator from the ground level to the main living areas, 4 bedrooms each with an ensuite bath and a spacious living area with a huge kitchen, formal...

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Islamorada Florida Vacation Rentals - Apartment
1 / 17

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$134 - $160
Per week:$934 - $1,120
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious...

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$100 - $134
Per week:$700 - $933
Pets allowed:No
Internet:Yes

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity...

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Long Key Florida Vacation Rentals - Apartment
1 / 2

Long Key Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 8
Apartment / 3 Bedrooms / Sleeps 8

from

$167

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Apartment
Per night:$167 - $194
Per week:$1,167 - $1,354
Pets allowed:No
Internet:No

MINIMUM STAY: 1 Month. This is a spacious bay front upscale half duplex with wrap around screened balcony overlooking the Florida Bay and just steps away from a swimming beach. Grab your towels and stroll over to the beach for a relaxing day. There are two large bedrooms, two full...

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Tavernier Florida Vacation Rentals - Home
1 / 25

Tavernier Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$150
Per week:$1,050
Pets allowed:No
Internet:Yes

Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This...

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Key West Florida Vacation Rentals - Apartment
1 / 21

Key West Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

(26)“ Excellent ”26 Reviews

from

$155

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$155 - $356
Per month:$4,650 - $10,680
Pets allowed:Yes
Internet:No

PARADISE PLACE – is a ground level one bedroom one bath condominium located in the Palm Gardens community in the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Paradise Place is part of a group of historic homes which have undergone complete...

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Key West Florida Vacation Rentals - Home
1 / 22

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$97 - $160
Per week:$677 - $1,120
Pets allowed:Yes
Internet:No

TRES GATOS: Spend a month (or two) in one of Key West's most revered neighborhoods and live like a local in this sweet 2- bedroom Conch cottage. A few blocks from Higgs Beach, Sandy's Cafe and the infamous Fausto's Food Palace; a quick bike ride to Duval Street. Open floor plan ...

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Key West Florida Vacation Rentals - Home
1 / 22

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 4
Home / 1 Bedroom / Sleeps 4

(5)“ Very Good ”5 Reviews

from

$67

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$67 - $100
Per week:$467 - $700
Pets allowed:Yes
Internet:Yes

VARELA COTTAGE - A true Conch cutie snuggled in Old Town. Varela Cottage is a 1. 5 bedroom 1 bath cottage with loft including a 2nd sleeping area. As you walk up to your front porch sitting area the front door opens and you enter into a cozy hideaway with amazing space. Tile entry...

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Key West Florida Vacation Rentals - Home
1 / 20

Key West Home
1 Bedroom / 2 Bathrooms / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$74

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$74 - $150
Per week:$514 - $1,050
Pets allowed:Yes
Internet:Yes

COCONUT COTTAGE - - Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West this one bedroom two bath cottage is...

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Key West Florida Vacation Rentals - Home
1 / 20

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

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

30 DAY MINIMUM RENTALWelcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off- street parking on either side (a rarity in Old Town! ) as well as an easy...

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Key West Florida Vacation Rentals - Home
1 / 7

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

30 DAY MINIMUM RENTAL .... NO PETS ACCEPTEDBreak away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the...

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Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:3
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

30 DAY MINIMUM RENTALCasa de Mundo is found on a quiet street in the Heart of Old Town. Set amid plumerias and palm trees, the property is conveniently located near favorite restaurants like Mangia Mangia, Michael's, Azur, 5 Brothers and Help Yourself. The modern interior adds...

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Key West Florida Vacation Rentals - Home
1 / 15

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Very Good ”1 Review

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

30 DAY MINIMUM RENTALLa Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard,...

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Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$127

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$127 - $150
Per week:$887 - $1,050
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...

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Islamorada Florida Vacation Rentals - Apartment
1 / 21

Islamorada Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$117 - $150
Per week:$817 - $1,050
Pets allowed:No
Internet:Yes

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting...

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About Florida Keys

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 ...

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