Search over 150,000 vacation rentals properties now! Click here to see more Vacation Homes
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.
-
Breezeswept Villa
Ocean Front Home w/Heated Pool, Dock, & WiFi available for monthly rental — Property 174010
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- waterfront
- pool
January 2010 is still available !!!S P E C I A L O F F E R- Rates (shown in USD)
- $750 - $1625 per property per week
-
Designer Decorated Oceanfront Acre Private Home, Private Heated Pool — Property 317093
- House
- 3 bedrooms , sleeps 10
- 2 bathrooms
- beach, waterfront
- garden
Special Weeks 11/28 & 12/5 $1300 EachS P E C I A L O F F E R- Rates (shown in USD)
-
Weekly Oceanfront Bungalow, Private Dock, Deep Channel, 80' Pool, Tenn — Property 315267
- House
- 2 bedrooms , sleeps 6
- 2 bathrooms
- resort, waterfront
- tennis court
Special last minute $700 week rate!S P E C I A L O F F E R- Rates (shown in USD)
-
Executive Ocean Front Florida Keys House with Pool — Property 168177
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- 1 half bathroom
- beach, waterfront
- pool
Thanksgiving Special Just $2975S P E C I A L O F F E R- Rates (shown in USD)
- $2750 - $4500 per property per week
-
3/2 Gorgeous Oceanfront Home - Bring Your Boat! — Property 252830
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- near the ocean, waterfront
- pool
- Rates (shown in USD)
- $1500 - $2850 per property per week
-
'Aqua Vistas'
OceanFRONT home new 2008, panoramic ocean views, pool, beach, WIFI - see Reviews — Property 186650
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- 1 half bathroom
- beach, waterfront
- pool
- Rates (shown in USD)
- $1990 - $3050 per property per week
-
Key West By Beach & Duval Street Old Town — Property 241481
- House
- 5 bedrooms , sleeps 12
- 4 bathrooms
- downtown, near the ocean
- pool
- Rates (shown in USD)
- $5700 - $6700 per property per week
-
Paradise Vacation Home-Heated Pool-Tiki-Waterfront — Property 173950
- House
- 2 bedrooms , sleeps 6
- 2 bathrooms
- near the ocean, waterfront
- garden
- Rates (shown in USD)
- $1500 - $2000 per property per week
-
Largest home at Truman Annex
'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites — Property 177191
- House
- 7 bedrooms , sleeps 12
- 7 bathrooms
- downtown, near the ocean
- balcony
- Rates (shown in USD)
- $7000 - $15000 per property per week
-
'Hidden Treasure' @ Casa East
'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool — Property 177317
- House
- 3 bedrooms , sleeps 6
- 3 bathrooms
- beach, near the ocean
- pool
- Rates (shown in USD)
- $1650 - $2750 per property per week
Refine Your Search
- You refined by:
- Florida Keys remove
- house remove
- pool remove
- (remove all)
Regions
Bedrooms
- 1 bedroom (17)
- 2 bedrooms (99)
- 3 bedrooms (146)
- 4+ bedrooms (124)
Sleeps
- Sleeps 1-4 (38)
- Sleeps 5-8 (254)
- Sleeps 9-12 (75)
- Sleeps 13 or more (19)
Baths
- 1 bathroom (38)
- 2 bathrooms (187)
- 3 bathrooms (94)
- 4+ bathrooms (64)
Amenities
- air conditioning (305)
- satellite or cable tv (226)
- internet access (183)
- dishwasher (324)
- washing machine (287)
Leisure Activities
- Florida Keys rentals near fishing (340)
- Florida Keys rentals near golf (270)
- Florida Keys rentals near skiing (7)
Suitability
- wheelchair accessible (21)
- suitable for elderly or infirm (55)
- pet friendly (82)
- non smoking only (349)
