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 Oceanfront, w/ Breathtaking views - 5 Star Resort — Property 129473

    Vacation Condo rental in Florida Keys area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • 1 half bathroom
    • resort, waterfront
    • accept credit card
    SPECIAL DISCOUNT SUMMER/FALL RENTAL!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1796 - $3495 per property per week

  2. Rent Your Own Private Island, Seabird Key, Marathon, Florida Keys — Property 102524

    Vacation House rental in Marathon area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Island September Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $5595 - $6995 per property per week

  3. Shipyard Treasure -- Luxury Truman Annex Condo in Old Town Key West — Property 203228

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 5
    • 1 bathroom
    • beach, downtown
    • swimming pool
    Reduced for September - $900 weekly
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1100 - $1600 per property per week

  4. Charming Key Largo Bayfront Home - Dock/Spa/Views — Property 147221

    Vacation House rental in Key Largo area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • waterfront
    • accept credit card
    Save 10% Now due to late cancellation
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1675 - $2275 per property per week

  5. Immaculate Fully Furnished 2/2 With Breathtaking Ocean Views — Property 167594

    Vacation Condo rental in Islamorada area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $1110 - $1250 per property per week

  6. 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

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

    Vacation House rental in Marathon area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)
    $1700 - $2400 per property per week

  8. Gerry's Florida House - What the Keys Were Meant to Be - - Private Pool, Spa, — Property 310111

    Vacation House rental in Marathon area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)

  9. Venetian Tropics, Islamorada Florida Keys, on deep canal and pool — Property 204162

    Vacation House rental in Islamorada area
    • House
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • swimming pool
    Rates (shown in USD)
    $2100 - $2900 per property per week

  10. NewTropical Pool Home, Cheeca guest access, walk to World wide sports — Property 206078

    Vacation House rental in Islamorada area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • downtown, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1500 - $2200 per property per week

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