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. New Luxurious Bay Harbour Waterfront Condo, 2 Master Bedrooms w/Private Baths — Property 321060

    Vacation Condo rental in Florida Keys area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • waterfront
    • swimming pool
    SAVE $$$ Last Minute Special: June 7-14
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1500 - $2200 per property per week

  2. Oceanfront Mansion — Property 104448

    Vacation House rental in Florida Keys area
    • House
    • 10 bedrooms , sleeps 20
    • 6 bathrooms
    • 1 half bathroom
    • town, waterfront
    • accept credit card
    Opening June 14-21 due to Cancellation
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. Key West Tropical Townhouse — Property 120270

    Vacation Townhome rental in Key West area
    • Townhome
    • 3 bedrooms , sleeps 8
    • 1 bathroom
    • beach, near the ocean
    • accept credit card
    Keys Summer Getaway!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  4. Luxurious Home in Pig Pine Key where the sky meets the sea! — Property 176992

    Vacation House rental in Big Pine Key area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • near the ocean, waterfront
    • swimming pool
    $500 off minimum 2 week stay
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1500 per property per week

  5. Ocean Front Pool Home on Ramrod Key - BRAND NEW — Property 174010

    Vacation House rental in Ramrod Key area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Ocean Front w/pool - Sept, Oct, Nov '08
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $688 - $1625 per property per week

  6. Key Largo Townhouse - Largest Pool In The Keys — Property 134306

    Vacation Townhome rental in Key Largo area
    • Townhome
    • 3 bedrooms , sleeps 8
    • 1 bathroom
    • 1 half bathroom
    • beach, resort
    • swimming pool
    Special Rates For Early Summer Bookings
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1800 - $2400 per property per week

  7. Owner Operated Waterfront Vacation Rental — Property 106890

    Vacation Condo rental in Key Colony Beach area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • swimming pool
    • air-conditioning
    20% Discount We Appreciate Your Business
    S P E C I A L    O F F E R
    Rates (shown in USD)

  8. Waterfront Paradise ** 75 Foot Dock with Private Beach ** Mile 74.5 — Property 101047

    Vacation House rental in Islamorada area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    15% Discount For May - last minute
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1500 per property per week

  9. 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 Usage of 22' Sailboat with cottage
    S P E C I A L    O F F E R
    Rates (shown in USD)

  10. Key Largo charming three story house with elevator — Property 186953

    Vacation House rental in Key Largo area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $1500 - $2250 per property per week

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