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.

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  1. Florida Keys Beach Home Heated pool Docks — Property 306629

    Vacation Townhome rental in Florida Keys area
    • Townhome
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Lowest rates in Florida Keys 2/2 Villa
    S P E C I A L    O F F E R
    Rates (shown in USD)

  2. Beach, pool, hot tub, TARPON & MANATEES at your dock! — Property 65912

    Vacation House rental in Florida Keys area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)
    $1800 - $2300 per property per week

  3. Paradise Vacation Home-Heated Pool-Tiki-Waterfront — Property 173950

    Vacation House rental in Florida Keys area
    • House
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $1500 - $2000 per property per week

  4. Atlantic Seclusion is very private with lush landscaping. — Property 208056

    Vacation House rental in Sugarloaf Key area
    • House
    • 3 bedrooms , sleeps 7
    • 2 bathrooms
    • waterfront
    • accept credit card
    Rates (shown in USD)
    $1550 per property per week

  5. Cabana del Sol - Waterfront Pool home-Private boat dock-Ocean Access — Property 192107

    Vacation House rental in Big Pine Key area
    • House
    • 3 bedrooms , sleeps 12
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $1600 - $1900 per property per week

  6. The Overlook at Big Pine Key - Waterfront Pool Home FALL SPECIALS — Property 309489

    Vacation House rental in Big Pine Key area
    • House
    • 2 bedrooms , sleeps 10
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1900 per property per week

  7. The Cottage at Big Pine Key- Hot Tub & Tiki Hut *Private boat dock — Property 315042

    Vacation House rental in Big Pine Key area
    • House
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $975 per property per week

  8. Gated Oceanfront Estate - Tropical Paradise - Pool & Boat Dock — Property 207734

    Vacation Hotel rental in Sugarloaf Key area
    • Hotel
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $3750 - $4950 per property per week

  9. The Beach House (Ocean Front) in Big Pine Key, FL-Amazing Ocean Views! — Property 147325

    Vacation House rental in Big Pine Key area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $2100 per property per week

  10. ~La Casa Habana~Paradise in a private retreat on Grassy Key. — Property 176323

    Vacation House rental in Grassy Key area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • village, waterfront
    • swimming pool
    Rates (shown in USD)
    $1900 - $3200 per property per week

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