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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. Futura Yacht Club
    Tropically Furnished Condo with Ocean Views — Property 301565

    Vacation Condo rental in Florida Keys area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • tennis court
    Discount $50.00 Off Weekly Rate
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $750 - $1000 per property per week

  2. Oceanfront, Tremendous Sunrise
    New Oceanfront, w/ Breathtaking views - 5 Star Resort - Huge Lagoon Pool — Property 129473

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • resort, waterfront
    • daily maid service
    Fall / Winter / Spring Special!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1495 - $2995 per property per week

  3. 5th Floor Oceanfront End Unit!
    Oceanfront 5th Floor End Unit! Pool, Internet, Tennis, Panoramic Ocean Views — Property 151910

    Vacation Condo rental in Islamorada area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, waterfront
    • sauna
    Christmas Week, $50 Discount
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $800 - $1500 per property per week

  4. Secret Garden in Key West — Property 168086

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • downtown, near the ocean
    • pool
    Nov. and Dec. special rate $975 per week
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $950 - $1900 per property per week

  5. Tad's Place
    Owner Operated Waterfront Vacation Rental — Property 106890

    Vacation Condo rental in Key Colony Beach area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • waterfront
    • pool
    800.00 Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $800 - $1100 per property per week

  6. Bay Harbour
    $100-$400 Off Luxurious Waterfront Condo, 2 Master Bedrooms w/Private Baths — Property 321060

    Vacation Condo rental in Islamorada area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • near the ocean, waterfront
    • jacuzzi
    Rates (shown in USD)
    $1500 - $2000 per property per week

  7. 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
    • balcony
    Rates (shown in USD)
    $800 - $1400 per property per week

  8. Kawama Tower Condo #302
    Luxurious Key Largo, Florida Keys Oceanfront Kawama Yacht Club 2+2 Condo — Property 191399

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • pool
    Rates (shown in USD)
    $900 - $1500 per property per week

  9. Quiet Oceanfront Condo with Superb Oceanview — Property 217210

    Vacation Condo rental in Islamorada area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, waterfront
    • tennis court
    Rates (shown in USD)
    $700 - $900 per property per week

  10. Oceanfront Beach Resort- Stunning Ocean Views - Free WIFI! — Property 119632

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • tennis court
    Rates (shown in USD)
    $800 - $1600 per property per week

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