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. The Mermaid House for Couples & Divers - Clean & Cozy — Property 201620

    Vacation Apartment rental in Florida Keys area
    • Apartment
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • near the ocean, town
    • air-conditioning
    Rates (shown in USD)
    $525 per property per week

  2. Waterfront Luxury in Old Town Key West — Property 166032

    Vacation Condo rental in Key West area
    • Condo
    • 1 bedroom , sleeps 5
    • 1 bathroom
    • resort, waterfront
    • accept credit card
    Rates (shown in USD)
    $1450 - $2420 per property per week

  3. Quiet Open Water Escape Overlooking Wildlife Sanctuary — Property 187803

    Vacation Villa rental in Marathon area
    • Villa
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • waterfront
    • accept credit card
    Rates (shown in USD)
    $1400 - $1600 per property per week

  4. Truman Annex - Just Renovated with Private Garden Area — Property 151840

    Vacation Condo rental in Key West area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, downtown
    • swimming pool
    Rates (shown in USD)

  5. Oceanfront Affordable Cottage with Dock, Kayaks and Pool — Property 319584

    Vacation Cottage rental in Cudjoe Key area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • waterfront
    • fishing
    Rates (shown in USD)

  6. Key West vacation condo in the Truman Annex — Property 209189

    Vacation Condo rental in Key West area
    • Condo
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • downtown, near the ocean
    • accept credit card
    Rates (shown in USD)
    $900 - $1450 per property per week

  7. Home- 60' Dock on Canal - Access to Gulf or Atlantic+ Cabana Club — Property 120326

    Vacation Townhome rental in Key Colony Beach area
    • Townhome
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • swimming pool
    Rates (shown in USD)

  8. Islamorada Beachfront Apartment - Spectacular Sunsets! — Property 184070

    Vacation Apartment rental in Islamorada area
    • Apartment
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)

  9. Key West cottage w. great price has it all,comfort, clean,quiet & great location — Property 184497

    Vacation rental in Key West area
    • 1 bedroom , sleeps 3
    • 1 bathroom
    • beach
    • air-conditioning
    Rates (shown in USD)
    $645 - $1150 per property per week

  10. Waterfront house with sailboat access — Property 192666

    Vacation House rental in Islamorada area
    • House
    • 1 bedroom , sleeps 6
    • 1 bathroom
    • beach, near the ocean
    • air-conditioning
    Rates (shown in USD)
    $950 - $1150 per property per week

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