Search for vacation rental homes on the Florida Keys
Have a Fling in the Florida Keys
The Florida Keys are a little wilder, a little bit beyond the typical Florida scene and perhaps a little closer to what you’re looking for in a romantic - yet not too distant - escape. You don’t have to worry about passports or language barriers down here; these islands may feel far away but they have a way of feeling like home, too. Thanks to the abundance of Florida Keys vacation rentals scattered about like so many conch shells, you can truly have it all as you finally treat yourself to a getaway built for two.
In Islamorada, Key Largo, Marathon and Key West (that’s just for starters) there are beach houses, condos, villas and cottages for everyone. You and your partner in crime (not that it should be deemed illegal to steal a long weekend and just enjoy yourselves) can take your pick from among luxury digs and modest love nests alike; head for a stretch of shoreline hopping with clubs and tiki bars or hide away on your own little island – literally.
Weigh your options, talk it over with your lucky companion and see how the scenario develops. Activities will range from diving and snorkeling to drinking and dancing, nodding off on the beach to nodding off next to your private pool…you set the schedule and itinerary as you please. You won’t be able to control the time of the sunset – or your amazement at its brilliance – but other than that the strings are yours to pull.
A popular place for weddings, honeymoons and lovey-dovey rendezvous, you’ll soon feel the good vibes for yourself. Maybe it’s the island culture, maybe it’s the chance to have the whole house to yourself; the point is, this trip will be good for you both.
-
Marathon Pool Home, 135 Ft. Dock, Waterfront, Balcony Sleeps 12 — Property 109763
- House
- 4 bedrooms , sleeps 12
- 5 bathrooms
- near the ocean, waterfront
- accept credit card
Labor Day Florida Keys Special 4/5 homeS P E C I A L O F F E R- Rates (shown in USD)
- $2100 - $5950 per property per week
-
Oceanfront Mansion — Property 104448
- House
- 10 bedrooms , sleeps 20
- 6 bathrooms
- 1 half bathroom
- town, waterfront
- accept credit card
August Availability 20% off reg PriceS P E C I A L O F F E R- Rates (shown in USD)
-
Oceanfront Cottage w/ Free 22' Sailboat, Kayaks, Snorkel/Fishing Gear — Property 162134
- House
- 1 bedroom , sleeps 4
- 1 bathroom
- resort, waterfront
- swimming pool
FREE to use Kayaks 22' sailboat fishingS P E C I A L O F F E R- Rates (shown in USD)
-
Oceanfront, new home with panoramic ocean views - Islamorada, FL — Property 186650
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- 1 half bathroom
- beach, waterfront
- swimming pool
- Rates (shown in USD)
- $1995 - $2950 per property per week
-
Ocean Side Waterfront Home - Pool , Tennis, Fishing — Property 317767
- House
- 4 bedrooms , sleeps 10
- 4 bathrooms
- near the ocean, waterfront
- swimming pool
- Rates (shown in USD)
- $3250 per property per week
-
Beautiful Private Oceanfront Executive Estate with Sugar Sand Beach, Heated Pool — Property 311833
- House
- 4 bedrooms , sleeps 8
- 4 bathrooms
- beach, waterfront
- swimming pool
- Rates (shown in USD)
- $3500 - $4300 per property per week
-
Cabana del Sol - Private boat dock & pool on the water — Property 192107
- House
- 3 bedrooms , sleeps 12
- 2 bathrooms
- near the ocean, waterfront
- accept credit card
- Rates (shown in USD)
- $1600 - $1900 per property per week
-
Large Oceanfront Home, Heated Pool, Dock-Weekly/Monthly — Property 309804
- House
- 4 bedrooms , sleeps 10
- 3 bathrooms
- waterfront
- accept credit card
- Rates (shown in USD)
-
Tranquility, Paradise, Come and Relax! Beautiful Vibrant Sunsets. — Property 315766
- House
- 2 bedrooms , sleeps 5
- 2 bathrooms
- beach, waterfront
- swimming pool
- Rates (shown in USD)
-
The White House Key West's Finest Monthly Rental/4 BR — Property 187082
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- town
- swimming pool
- Rates (shown in USD)
- $1375 - $2125 per property per week
Refine Your Search
- You refined by:
- Florida Keys remove
- house remove
- pool remove
- (remove all)
Regions
Bedrooms
- 1 bedroom (1)
- 2 bedrooms (43)
- 3 bedrooms (64)
- 4+ bedrooms (55)
Sleeps
- Sleeps 1-4 (13)
- Sleeps 5-8 (99)
- Sleeps 9-12 (39)
- Sleeps 13 or more (12)
Baths
- 1 bathroom (7)
- 2 bathrooms (85)
- 3 bathrooms (40)
- 4+ bathrooms (27)
Amenities
- air conditioning (157)
- satellite or cable tv (137)
- internet access (122)
- dishwasher (154)
- washing machine (148)
Leisure Activities
- Florida Keys rentals near fishing (156)
- Florida Keys rentals near golf (109)
- Florida Keys rentals near skiing (9)
Suitability
- wheelchair accessible (25)
- suitable for elderly or infirm (56)
- pet friendly (53)
- non smoking only (123)
