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.
-
5 Star Oceanfront Resort - Key Largo's Most Upscale Destination - Free WIFI! — Property 134355
- Villa
- 2 bedrooms , sleeps 6
- 2 bathrooms
- near the ocean, resort
- jacuzzi
- Rates (shown in USD)
- $1200 - $2100 per property per week
-
Quiet Open Water Retreat On Nature Refuge — Property 177132
- Villa
- studio , sleeps 2
- 1 bathroom
- waterfront
- terrace
- Rates (shown in USD)
- $1000 - $1200 per property per week
-
Quiet Open Water Hideaway Overlooking Wildlife Preserve — Property 237766
- Villa
- 2 bedrooms , sleeps 4
- 1 bathroom
- waterfront
- balcony
- Rates (shown in USD)
- $1200 - $1400 per property per week
-
Ocean Retreat - 1 Week Minimum — Property 72387
- Villa
- 3 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- coffee maker
- toaster
- Rates (shown in USD)
- $2400 - $4400 per villa per week
-
Duval St. 6 bedroom Compound
Duval St. 6 bedroom Compound w/ 2 Private Heated Pools, Parking & Huge Roof Deck — Property 228157
- Villa
- 6 bedrooms , sleeps 14
- 5 bathrooms
- 2 half bathroom
- downtown, near the ocean
- pool
- Rates (shown in USD)
- $8000 per property per week
-
Little Bay — Property 7011707
- Villa
- 2 bedrooms , sleeps 6
- 2 bathrooms
- air-conditioning
- balcony
- Rates (shown in USD)
- $2400 per villa per week
-
Quiet Open Water Escape Overlooking Wildlife Sanctuary — Property 210446
- Villa
- 1 bedroom , sleeps 2
- 1 bathroom
- waterfront
- terrace
- Rates (shown in USD)
- $1400 - $1600 per property per week
-
Mitchell's Keys Villa - Private, Secluded House on the Bay — Property 236873
- Villa
- 2 bedrooms , sleeps 4
- 1 bathroom
- waterfront
- pets considered
- Rates (shown in USD)
- $795 - $1095 per property per week
-
Quiet Open Water Hideaway On Wildlife Preserve — Property 225025
- Villa
- 2 bedrooms , sleeps 4
- 1 bathroom
- waterfront
- balcony
- Rates (shown in USD)
- $1200 - $1400 per property per week
-
Southernmost Southernmost Home
The ultimate place to stay in Key West — Property 256853
- Villa
- 4 bedrooms , sleeps 8
- 5 bathrooms
- 1 half bathroom
- town, waterfront
- pool
- Rates (shown in USD)
- $7000 - $8500 per property per week
Refine Your Search
- You refined by:
- Florida Keys remove
- villa remove
- (remove all)
Regions
Bedrooms
- Studio (1)
- 1 bedroom (3)
- 2 bedrooms (10)
- 3 bedrooms (9)
- 4+ bedrooms (7)
Sleeps
- Sleeps 1-4 (9)
- Sleeps 5-8 (16)
- Sleeps 9-12 (4)
- Sleeps 13 or more (1)
Baths
- 1 bathroom (8)
- 2 bathrooms (13)
- 3 bathrooms (4)
- 4+ bathrooms (5)
Amenities
- air conditioning (29)
- satellite or cable tv (26)
- pool (18)
- internet access (21)
- dishwasher (25)
- washing machine (29)
Leisure Activities
Suitability
- wheelchair accessible (4)
- suitable for elderly or infirm (7)
- pet friendly (5)
- non smoking only (23)
