Updating...

More filters (1)

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Clothes dryer
Table tennis
Pool or snooker table
Games room
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Fax machine
Swing set or jungle gym
Video player
Stove
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Fridge
Boat available
Freezer
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Children - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

See all

Less

Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

See all

Less

101 houses

Sort by:

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Sugarloaf house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

Match: Rental types Fridge

All filters match

Price per night from

$458

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Fridge, Rental types

1 of 2 filters match

Price per night from

$203

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Fridge, Rental types

1 of 2 filters match

Price per night from

$257

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Fridge, Rental types

1 of 2 filters match

Price per night from

$230

Florida Keys at it's best

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Fridge, Rental types

1 of 2 filters match

Price per night from

$241

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Fridge, Rental types

1 of 2 filters match

Price per night from

$332

Great rentals within 20 miles that match your search

Coconuts on the Water

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

Match: Rental types Fridge

All filters match

Price per night from

$205

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

Match: Rental types Fridge

All filters match

Price per night from

$514

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types Fridge

All filters match

Price per night from

$327

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Rental types Fridge

All filters match

Price per night from

$744

Moveable Feast

Key West house

4 bedrooms
5 bathrooms

sleeps 10

Match: Rental types Fridge

All filters match

Price per night from

$430

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

Match: Rental types Fridge

All filters match

Price per night from

$344

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Rental types Fridge

All filters match

Price per night from

$573

The Mermaids House, Historic Old Town Key West

Key West house

2 bedrooms
1 bathroom

sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

Match: Rental types Fridge

All filters match

Price per night from

$328

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

Match: Rental types Fridge

All filters match

Price per night from

$791

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

Match: Rental types Fridge

All filters match

Price per night from

$622

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

4 bedrooms
2 bathrooms

sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

Match: Rental types Fridge

All filters match

Price per night from

$544

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms
3 bathrooms

sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

Match: Rental types Fridge

All filters match

Price per night from

$344

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms
1 bathroom

sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

Match: Rental types Fridge

All filters match

Price per night from

$134

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

5 bedrooms
6 bathrooms

sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

Match: Rental types Fridge

All filters match

Price per night from

$2,120

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom
1 bathroom

sleeps 4

Match: Rental types Fridge

All filters match

Price per night from

$1,144

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

4 bedrooms
2 bathrooms

sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

Match: Rental types Fridge

All filters match

Price per night from

$2,062