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. Beautiful Duval St. Condo, Location, Location!!!! — Property 156723

    Vacation Condo rental in Florida Keys area
    • Condo
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • downtown, near the ocean
    • accept credit card
    Great Fall Weekly Rates!!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1200 - $1800 per property per week

  2. Luxurious Oceanfront Resort-ENDLESS OCEAN VIEWS FROM INSIDE & OUT — Property 190239

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    $100 OFF per Week Fall Special!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $850 - $1995 per property per week

  3. New Oceanfront w/ Breathtaking views - 5 Star Resort — Property 129473

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • 1 half bathroom
    • resort, waterfront
    • accept credit card
    Fantastic Summer / Fall Special!!! Call!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1796 - $3495 per property per week

  4. Villa Nomade, Elegant Truman Annex condo in the heart of Old Town — Property 158403

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • downtown, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1200 - $2000 per property per week

  5. Oceanfront Condo: Ocean View, Beach, Marina and Tennis — Property 140420

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $975 per property per week

  6. Penthouse Condo Fabulous Sunsets in Key Largo — Property 69815

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)
    $895 - $1995 per property per week

  7. Oceanfront Two Bed-Two Bath Kawama Tower Condo W/ Boat Slip — Property 157904

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)

  8. Key Largo Mar-a-Villa, Kawama Yacht Club — Property 200310

    Vacation Condo rental in Key Largo area
    • Condo
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)

  9. Direct Oceanfront Free Wireless Internet — Property 149233

    Vacation Condo rental in Key West area
    • Condo
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • beach
    • accept credit card
    Rates (shown in USD)
    $2350 per property per week

  10. Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals) — Property 112032

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)

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