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

1-50 of 231 Florida Keys Rentals

Sort:
1  2  3  4  5 
Key Largo Florida Vacation Rentals - Home
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...

See more

Close x

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 ...

See more

Close x

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...

See more

Close x

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,...

See more

Close x

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

See all reviews

Close x

1 / 25

Key West Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$865

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Home
Per night:$865 - $1,225
Per month:$25,950 - $36,750
Pets allowed:No
Internet:Yes

THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants,...

See more

Close x

Amazing location for fun filled girls getaway!

“ Excellent ”
September 12, 2013
I was very impressed with the house. It was perfectly located so that we didn't have to rent bikes or move the car often. We absolutely loved lounging at the pool and couldn't have asked for a better lay out for our 7 girls retreat weekend. We will absolutely stay here again. I am missing it already and we all can't stop talking about it. Thank you for the perfect long weekend away!
Katie Skiff, Washington, DC

See all reviews

Close x

Key Largo Florida Vacation Rentals - Home
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...

See more

Close x

Marathon Florida Vacation Rentals - Home
1 / 30

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$414

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$414 - $671
Per week:$2,895 - $4,695
Pets allowed:Yes
Internet:Yes

This is a rare 4 bedroom, 4 bath waterfront home near the Vaca Cut on the Gulf of Mexico. This home features a pool, beach sand backyard and kayaks. Bring your own boat or rent one from us for $695/week (17 foot center console with 50HP engine). This property is located adjacent...

See more

Close x

FUN!!!

“ Excellent ”
December 3, 2014
We had a wonderful stay here.The location is perfect.Lots to do and see!!Thank you
Heather Gerhold, Florida

See all reviews

Close x

Key Largo Florida Vacation Rentals - Home
1 / 23
Bedrooms:3
Bathrooms:2
Sleeps:9
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

Beautiful 2 story 3 bedroom 2 baths home. Located in Key Largo at MM 103 on the bayside and close to John Pennekamp Park, local shopping, fine restaurants, diving, charter fishing or just swimming with the dolphins! This home has an open water view overlooking the beautiful Florida...

See more

Close x

Relaxing in Key Largo

“ Excellent ”
January 4, 2015
We had a relaxing and enjoyable stay at this house. It had everything we needed and more. Our kids enjoyed kayaking in the canals and out to the bay. We saw manatees in the canal. House is convenient to shopping and tourist attractions. I would recommend this house for any stay in Key Largo.
Mary Anne Feucht, Ponder, TX USA

See all reviews

Close x

Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$184

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$184 - $200
Per week:$1,284 - $1,400
Pets allowed:Yes
Internet:No

This spacious, Caribbean- style vacation home comes equipped with its own private swimming pool and great deep- water canal. This beautiful home has three stories including a super play room off the pool area with a ping- pong table and a big screen TV for the kids. The 2nd floor...

See more

Close x

Key Largo Florida Vacation Rentals - Condo
1 / 23

Key Largo Condo
3 Bedrooms / 1.5 Bathrooms / Sleeps 7

“ Excellent ”2 Reviews

from

$136

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:7
Type:Condo
Per night:$136 - $172
Per week:$950 - $1,200
Pets allowed:No
Internet:Yes

Bay front Vacation Condo in Key Largo, Florida. We book early so don't wait, beat the rest to one of the best and most reasonable, clean, and well appointed condos in beautiful Key Largo, Florida. Max 4 adults, up to 3 children. 2 large bedrooms with Kings size beds,...

See more

Close x

Key Largo vacation Condo

“ Excellent ”
January 9, 2015
Exelent!
Milos Krunic, Woodbridge, ON, Canada

See all reviews

Close x

1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$143

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$143 - $200
Per week:$1,000 - $1,400
Pets allowed:No
Internet:Yes

Two oceanfront condominiums ranch style situated on floor 2 and 5 about 50 ft from the water . You can hear and see the fish break the water in the morning. There are a variety of large tropical birds to watch . We have a beautiful pool among lush tropical foliage on the ocean. We...

See more

Close x

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...

See more

Close x

Little Torch Key Florida Vacation Rentals - Home
1 / 8

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

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$117 - $127
Per week:$817 - $887
Pets allowed:Yes
Internet:Yes

Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this 3 bedroom, 2 bath, Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine Channel, gulf side. All the rooms are spacious...

See more

Close x

1 / 8

Ramrod Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$167

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$167 - $174
Per week:$1,167 - $1,214
Pets allowed:Yes
Internet:No

Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home is glass for endless views of the blue- green waters of the Florida Keys. Equipped with all the comforts of home plus a heated pool. The open porch catches the breeze, and the...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 37

Key West Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$340

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$340 - $470
Per month:$10,200 - $14,100
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...

See more

Close x

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.

See all reviews

Close x

1 / 8

Sugarloaf Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$130

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$130 - $140
Per week:$910 - $980
Pets allowed:No
Internet:No

Ibis Landing is truly a remarkable property nestled by the Great White Heron Wildlife Refuge. Acres of nature's wonders can be viewed from the 2 large open decks. Open water views abound from every direction. The long walk out dock wanders through the undisturbed mangrove tidal flats...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 29

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”4 Reviews

from

$415

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$415 - $458
Per week:$2,900 - $3,200
Pets allowed:No
Internet:Yes

Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of...

See more

Close x

getaway

“ Excellent ”
January 23, 2015
5 girlfriends snuck away for a long weekend retreat to celebrate a birthday. The house had all that we needed! We loved all of the "extras" including the Gheenoe, the kayak, the bikes, the hammocks. They made the trip extra special. The house was super clean, and we are tough critics! A wonderful time and easy access to fun activities, restaurants, beaches, etc. nearby
Terri woellner, Denver

See all reviews

Close x

Key Largo Florida Vacation Rentals - Home
1 / 18

Key Largo Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”2 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$250
Per week:$1,500
Pets allowed:Yes
Internet:Yes

lovely Key Largo retreat is located on MM106 on the Bay side. our home sleeps 7 comfortably with 3 bedrooms and 2 bath. we offer Beautiful direct open bay view from almost every room in the home. 150 foot dock area and plenty of parking ! After a long day of fun in the sun...

See more

Close x

Tropical Haven vacation of the decade!

“ Excellent ”
July 27, 2014
We rented "Casablanca" for a week of heaven in July. The home is wonderful for family and friends with a large open kitchen super for fun mealtimes. We called it the "island" because we felt like we were in our own little slice of tropical paradise. With lots of dockage space and a phenomenal view we could look out at the bay. Manatees swam next to the dock every day. We had fun feeding them cabbage and taking pictures to treasure the memory. The hot tub was a great way to start the morning with a cup of coffee and chatting about the plan for the day. We rode our bikes to the grocery store, cycled to the state park, ran in the neighborhood. It was great that we could get out into the bay in a heart beat and to the ocean after a short motor to Adam's Cut. Snorkeling was just a short boat trip away. The porch the full length of the house was wonderful for spending hours playing music, knitting, or any hobby. I loved the fan on the porch which kept us cool and comfortable and kept the mosquitos away. The children and adults both enjoyed playing pool and darts and honing our skills. Thank you so much Helen for sharing your home with us! It was clean, charming, and just a fantastic location to enjoy the treasured time our family had there. We can't wait to return!
Terese McMahon, Pompano Beach, FL

See all reviews

Close x

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...

See more

Close x

Key Largo Florida Vacation Rentals - Cottage
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 ...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 28

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 12

from

$550

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$550 - $750
Per week:$3,850 - $5,250
Pets allowed:No
Internet:Yes

Great house in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches. Lovely master suite on the top floor with it's own balcony. Modern house with stylish, comfortable furnishings. 90 feet of excellent deep water dockage on a wide canal leading directly...

See more

Close x

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,...

See more

Close x

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

See all reviews

Close x

Marathon Florida Vacation Rentals - Cottage
1 / 15

Marathon Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$413

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$413
Per week:$2,890
Pets allowed:No
Internet:Yes

Sunset Bay is a 3 bedroom, 2 bathroom home located on the clear, aquamarine waters of the beautiful Gulf of Mexico. This beautiful waterfront cottage features a screened veranda and a natural native garden. This is a completely furnished home with an open living room, dining room,...

See more

Close x

Great family vacation!

“ Excellent ”
June 19, 2014
We had a great time in the keys! The house is easy to get to and beautiful! There was plenty if space for all of us. The kids loved swimming in the pool and fishing off the dock. We saw a manatee and hooked a tarpon in the canal. We rented kayaks and explored the area. Check in and check out were easy. Can't wait to visit again!
Kathy Ford Goldstein, Colorado, USA

See all reviews

Close x

Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$250 - $267
Per week:$1,750 - $1,867
Pets allowed:No
Internet:Yes

You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone...

See more

Close x

Big Pine Key Florida Vacation Rentals - Home
1 / 5

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

“ Excellent ”7 Reviews

from

$313

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
Per night:$313
Per week:$2,188
Pets allowed:Yes
Internet:Yes

This house is located in Long Beach Estates, one of the most private neighborhoods in the Keys. It is a private peninsula that is cushioned by a large beautiful wildlife preserve with deep water access within minutes to Looe Key. This is a spacious, waterfront home on open water,...

See more

Close x

Excellent week at a wonderful house!

“ Excellent ”
June 9, 2014
My husband and I took my daughter her husband and our 3 grandchildren for a week. The house was perfect for our size group. Huge kitchen and great room, 3 big bedrooms and the best part 3 bathrooms! We used our boat everyday, getting out of the canal is really easy and there is a boat ramp right around the corner from the house.The tiki hut out back is awesome. And of course the Key deer are one of our favorite things about Big Pine and they just wander around the neighborhood. My grandchildren thought that was the coolest thing.We had a blast and would definitely rent this house again.
Carlene Rozalsky, Grant, FL

See all reviews

Close x

Marathon Florida Vacation Rentals - Home
1 / 8

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$329

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$329
Per week:$2,300
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 ...

See more

Close x

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

See all reviews

Close x

Tavernier Florida Vacation Rentals - Home
1 / 40

Tavernier Home
6 Bedrooms / 6 Bathrooms / Sleeps 22

“ Excellent ”1 Review

from

$567

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:22
Type:Home
Per night:$567
Per week:$3,967
Pets allowed:No
Internet:Yes

This three story house, with a breathtaking view , sits on the edge of the Atlantic Ocean with no end in sight. To accompany the great Atlantic is a grand 3, 800 sq ft. 8 bedroom and 6 bathroom home with a pool and a large and complete Kitchen and can accommodate up to 27 people...

See more

Close x

Great reunion spot!

“ Excellent ”
January 2, 2014
This beautiful home was perfect for our recent Christmas get together with family from far and wide. Eighteen of us, including a baby, enjoyed spacious rooms and lovely amenities. The channel offered a great launch spot for the paddle boat ( included) and the kayaks we rented. The indoor dining room and the patio eating area made for terrific family meals. The nearby community center provided fun swimming and tennis at no cost. We really enjoyed our vacation in this beautiful location!
Tim Riazzi, Dayton, Ohio USA

See all reviews

Close x

Key Largo Florida Vacation Rentals - Home
1 / 8

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$65

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$65 - $89
Per week:$455 - $619
Pets allowed:Yes
Internet:Yes

Enjoy the real Keys atmosphere. Large (40’ by 16’) screened porch area, complete with kitchen (including automatic dishwasher), Tiki Bar, Hot Tub, Sleeper sofa, large patio table with comfortable chairs. Recently remodeled main bathroom with new front loading washer and dryer....

See more

Close x

Marathon Florida Vacation Rentals - Home
1 / 12

Marathon Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

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, ...

See more

Close x

Islamorada Florida Vacation Rentals - Cottage
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 ...

See more

Close x

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,...

See more

Close x

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...

See more

Close x

Marathon Florida Vacation Rentals - Villa
1 / 22

Marathon Villa
3 Bedrooms / 3 Bathrooms / Sleeps 7

from

$243

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Villa
Per night:$243 - $315
Per week:$1,700 - $2,200
Pets allowed:No
Internet:Yes

Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2, 000 square feet on 2 levels with under cover parking....

See more

Close x

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....

See more

Close x

Key Largo Florida Vacation Rentals - Home
1 / 52

Key Largo Home
5 Bedrooms / 3 Bathrooms / Sleeps 16

“ Excellent ”25 Reviews

from

$500

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:16
Type:Home
Per night:$500
Per week:$3,500
Pets allowed:No
Internet:Yes

Have you ever been in paradise? If not, this is the closest you will ever be, wake up to a beautiful sunrise and aqua blue water of the bay , occasional flock of Iris roaming around the yard , while the palm trees swing from the ocean breeze, this house with its unique architectural...

See more

Close x

Very Relaxing - Quiet New Year

“ Excellent ”
January 8, 2015
We had 10 adults and 2 grandchildren in the home for a full week. Everyone had a great time - we really enjoyed the grill by the pool and the Tiki hut that we had dinner under almost every night by the water. The pool was a little cool but with the warm temps it was fine for the kids - we even snorkeled off the dock and caught a few fish as well. Overall, the vacation for our family was fantastic. Nemer was very gracious in helping us out with a couple things and even checked in on us a couple times. The kitchen is perfect for a large group to cook meals in as well. It is like having your own resort on a smaller scale and you don't have to deal with the crowds! Thanks again for a great week. We will definitely look at Key Largo for future family vacations. Temps were perfect for us.
Dewayne White, Nashville, TN

See all reviews

Close x

Key Largo Florida Vacation Rentals - Home
1 / 21

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$117

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$117
Per week:$817
Pets allowed:No
Internet:No

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...

See more

Close x

1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$104

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$104 - $114
Per week:$724 - $794
Pets allowed:No
Internet:No

This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and features 3 bedrooms and 2 bathrooms as well as a roomy loft area. You’ll enjoy an open living plan with a nice size full kitchen with plenty of counter room,...

See more

Close x

Atlantic Breezes January Rental.

“ Excellent ”
February 14, 2014
the house was as discribed,very nice everything in great condition,boat access to Bow Chanel great.Will rent this house again ASAP. Peter Hillmann
Peter Hillmamm, Brookfield,Illinois

See all reviews

Close x

Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$230

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$230 - $240
Per week:$1,610 - $1,680
Pets allowed:Yes
Internet:No

Surrounded by lush, tropical landscaping, this gated open- water vacation home comes equipped will all the thoughtful touches of home and so much more. Choose the fantastic top floor master bedroom with Jacuzzi tub and sitting room or one of the other fantastic rooms! Enjoy...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”2 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$210 - $342
Per month:$6,300 - $10,260
Pets allowed:No
Internet:Yes

TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back...

See more

Close x

A heart-warming and tranquil oasis

“ Excellent ”
August 1, 2013
We truly enjoyed our stay at Tranquility on Olivia Street. The neighbourhood is charming and very peaceful. There are many interesting restaurants to discover in the surroundings and many other services easily accessible at walking and biking distance. We enjoyed relaxing in the swimming pool at the end of the day and meeting many of the interesting folks renting other cottages at the Colony. I highly recommend Tranquility for its location, the peaceful neighbourhood, the physical setting at the Colony, and the charming interior decoration of the cottage. The colors are fresh, bright and full of joy. Our only recommendation would be to provide vacationers with a binder presenting essential information on things to do, to see and, especially, a list of surrounding service providers such as: grocery store, fish market, pharmacy, bike rental, local restaurants, and hospital in case of emergency. The sofa-bed mattress would need to be changed. It’s really not comfortable. And finally, the master bedroom air conditioner is quite noisy. Should we plan to visit the Keys in the near future, Tranquility would be our place to stay. What a great place to call home for a week on vacation. Thanks!
Paul Turpin, Key West, FL, USA

See all reviews

Close x

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 ...

See more

Close x

Key Largo Florida Vacation Rentals - Condo
1 / 16

Key Largo Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$97 - $110
Per week:$677 - $770
Pets allowed:No
Internet:Yes

As one of Buttonwood Bays highly sought after condo units this 2 bedroom 2 bathroom home will charm you and warm you! With easy elevator access you are located on the third floor with spectacular views overlooking the entrance to Buttonwood Bay's private coral rock harbor. Only...

See more

Close x

Key Largo Florida Vacation Rentals - Villa
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,...

See more

Close x

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

See all reviews

Close x

Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$120

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$120 - $130
Per week:$840 - $910
Pets allowed:Yes
Internet:No

Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Keys has to offer. This home offers...

See more

Close x

1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$175 - $324
Per month:$5,250 - $9,720
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...

See more

Close x

Marathon Florida Vacation Rentals - Home
1 / 17

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $450
Per week:$1,050 - $3,150
Pets allowed:No
Internet:Yes

2 bedroom 2 bathroom vacation villas on Atlantic Ocean. Heated pool overlooking a natural sand beach & Tiki huts & hammocks. All homes have full kitchen, 3 TV’s, and Washer & Dryer. Boat docks are available on site. Bar B Q grills. 2 Zone air- conditioning in every villa....

See more

Close x

5 night stay in marathon

“ Excellent ”
January 15, 2015
Very enjoyable; nicely refurbished older facility. The only real issue for us was that you must climb stairs to enter unit. This puts you on kitchen/dining level. You then climb internal circular stairs to reach bedrooms, bathrooms and living room. The second set of stairs are nearly impossible to make with a larger suitcase. We finally left ours on the first level.The beach area was very nice and the pool and hot tub were great after a long day. We would consider this again for the future.
ray rose, Tulsa, OK

See all reviews

Close x

Living Room with 42" SONY LED, BOSE surround sound and screened deck
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$250 - $500
Per month:$7,500 - $15,000
Pets allowed:No
Internet:Yes

"TEE BY THE SEA" vacation rental (we include 8 bikes free for our guests! ! ! ) If you love... GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT... than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island....

See more

Close x

Key West

“ Excellent ”
May 6, 2013
The unit was very comfortable and well equipped. The pool area was terrific and location to Key West couldn't be better. The only thing we found negative at all was the close proximity to the road but that being said it did not ruin our visit. We would stay here again.
Veronica Laliberte, Oakville, Ontario Canada

See all reviews

Close x

Marathon Florida Vacation Rentals - Townhouse
1 / 20

Marathon Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 7

“ Excellent ”4 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 openwater 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...

See more

Close x

Great Place to stay

“ Excellent ”
May 14, 2014
We have stayed in this house many times in the past. House was clean and in great shape. We had a fun time and will be back. RBG
Richard Greene, Maine

See all reviews

Close x

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 ...

See more

Close x

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...

See more

Close x

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

See all reviews

Close x

1  2  3  4  5 

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.
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More