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.

  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(1 - 10 of 308)

  1. Marathon Pool Home, 135 Ft. Dock, Waterfront, Balcony Sleeps 12 — Property 109763

    Vacation House rental in Florida Keys area
    • House
    • 4 bedrooms , sleeps 12
    • 5 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Labor Day Florida Keys Special 4/5 home
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2100 - $5950 per property per week

  2. Oceanfront Mansion — Property 104448

    Vacation House rental in Islamorada area
    • House
    • 10 bedrooms , sleeps 20
    • 6 bathrooms
    • 1 half bathroom
    • town, waterfront
    • accept credit card
    August Availability 20% off reg Price
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. Key West Luxury - Tropical Home — Property 181296

    Vacation House rental in Key West area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • downtown, near the ocean
    • accept credit card
    Cleaning Fee waived for Aug-Sept bookings
    S P E C I A L    O F F E R
    Rates (shown in USD)

  4. Oceanfront Cottage w/ Free 22' Sailboat, Kayaks, Snorkel/Fishing Gear — Property 162134

    Vacation House rental in Key Largo area
    • House
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • resort, waterfront
    • swimming pool
    FREE to use Kayaks 22' sailboat fishing
    S P E C I A L    O F F E R
    Rates (shown in USD)

  5. Oceanfront, new home with panoramic ocean views - Islamorada, FL — Property 186650

    Vacation House rental in Islamorada area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $1995 - $2950 per property per week

  6. Your new property advertisement — Property 190220

    Vacation House rental in Key Largo area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • air-conditioning
    • washing machine
    Rates (shown in USD)
    $1400 - $1800 per property per week

  7. Ocean Side Waterfront Home - Pool , Tennis, Fishing — Property 317767

    Vacation House rental in Marathon area
    • House
    • 4 bedrooms , sleeps 10
    • 4 bathrooms
    • near the ocean, waterfront
    • swimming pool
    Rates (shown in USD)
    $3250 per property per week

  8. The Lodge - WATERFRONT-PRIVATE BOAT DOCK-GREAT FISHING! — Property 166614

    Vacation House rental in Big Pine Key area
    • House
    • 2 bedrooms , sleeps 6
    • 1 bathroom
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $875 - $995 per property per week

  9. Beautiful Private Oceanfront Executive Estate with Sugar Sand Beach, Heated Pool — Property 311833

    Vacation House rental in Islamorada area
    • House
    • 4 bedrooms , sleeps 8
    • 4 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $3500 - $4300 per property per week

  10. Key Largo Oceanfront home w/Sandy Beach — Property 190523

    Vacation House rental in Key Largo area
    • House
    • 4 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)
    $3800 - $5000 per property per week

Refine Your Search

You refined by:
Florida Keys remove
house remove
(remove all)
Find by availability dates:

Regions

Bedrooms

Sleeps

Baths

Amenities

Leisure Activities

Suitability

Other

  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(1 - 10 of 308)