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

    Vacation Condo rental in Florida Keys 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

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

    Vacation Townhome rental in Marathon area
    • Townhome
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Florida Keys Fall 2/2 Villa beach pool
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $918 - $1732 per property per week

  3. Marathon Pool Home, 135 Ft. Dock, Waterfront, Balcony Sleeps 12 — Property 109763

    Vacation House rental in Marathon area
    • House
    • 4 bedrooms , sleeps 12
    • 5 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Labor Day Florida Keys Special 4/5 home
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2100 - $5950 per property per week

  4. Luxury Waterfront at the Galleon Resort in Old Town — Property 161268

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • resort, waterfront
    • accept credit card
    $2,150/week - August & September
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2750 - $3850 per property per week

  5. Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock — Property 113802

    Vacation Condo rental in Marathon area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • near the ocean, waterfront
    • swimming pool
    $100.00 Per Week Gasoline Rate Reduction
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1086 - $1586 per property per week

  6. 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

  7. Oceanfront Mansion — Property 104448

    Vacation House rental in Islamorada area
    • House
    • 10 bedrooms , sleeps 20
    • 6 bathrooms
    • 1 half bathroom
    • town, waterfront
    • accept credit card
    August Availability 20% off reg Price
    S P E C I A L    O F F E R
    Rates (shown in USD)

  8. La Casa Grande — Property 173152

    Vacation Estate rental in Islamorada area
    • Estate
    • 6 bedrooms , sleeps 12
    • 6 bathrooms
    • 2 half bathroom
    • beach, near the ocean
    • accept credit card
    1000.00 off regular weekly rate
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $7500 per property per week

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

    Vacation Condo rental in Key West 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

  10. Key West Luxury - Tropical Home — Property 181296

    Vacation House rental in Key West area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • downtown, near the ocean
    • accept credit card
    Cleaning Fee waived for Aug-Sept bookings
    S P E C I A L    O F F E R
    Rates (shown in USD)

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