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Holiday rentals in Florida Keys

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Florida Keys

Guests agree: these stays are highly rated for location, cleanliness, and more.

Waterfront Villa-Bring Your Boat Cabana Club Beach
Entire residential home · 5 guests · 3 beds · 2 bathrooms

Waterfront Villa-Bring Your Boat Cabana Club BeachNew Listing! Beautiful, clean 2/2 villa with 40ft dock- bring your boat up to 50ft. Open concept with water views, great location in beautiful Key Colony Beach, walk to the beach, pool and tiki bar at the Cabana Club (membership included with the rental), close to Marathon and centrally located between Islamorada and Key West. Relax and grill on the back patio or use of our ocean kayaks on the beautiful canal. 10 minute ocean and gulf access, close to restaurants, shopping and nightlife.

Private waterfront sleeps 10 dock heated pool pets
SUPERHOST
Entire residential home · 10 guests · 6 beds · 2 bathrooms

Private waterfront sleeps 10 dock heated pool petsBeautiful waterfront home, sleeping 10, in the heart of Marathon. Private setting with over 2 acres of land. Plenty of parking for cars, trailers or RVs. Protected dockage for multiple small or large boats. Perfect for a family trip or fisherman's getaway. Pet-Friendly. Families can enjoy the space with a heated pool, outside grill, and sunset views. Cook your catch! Working from home? Make our home with high-speed WiFi your waterfront workspace. Pet friendly.

Casa Mariposa:  Sombrero Beach Neighborhood
SUPERHOST
Private room · 2 guests · 2 beds · 1 private bathroom

Casa Mariposa: Sombrero Beach NeighborhoodBook your late summer or fall getaway now! Join us in Marathon, in the heart of the Florida Keys in our 100% solar-powered retreat. We look forward to hosting you. Stay in a private suite in our ground-level home. Enjoy our 50' lap pool, large patio, and tropical gardens. Launch rented kayaks from Sombrero Beach, or enjoy activities anywhere in the Keys from our central location. Contact us if you are interested in a variation in the length of your stay.

Holiday rentals for every style

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Popular amenities for Florida Keys holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Florida Keys

SUPERHOST
  1. Entire guest house
  2. Key Colony Beach
Oct. 2-9th $140 !! Paradise found! 3/2 Key Colony
SUPERHOST
  1. Private room
  2. Marathon
Casa Mariposa: Easy walk to Sombrero Beach
SUPERHOST
  1. Private room
  2. Big Pine Key
Old Island Life
SUPERHOST
  1. Hotel room
  2. Key West
Poolside Queen Room steps from Duval St!
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Pulpo Cottage
  1. Entire residential home
  2. Key Colony Beach
NEW LISTING-KEYS COTTAGE-WATERFRONT-PET FRIENDLY
SUPERHOST
  1. Entire townhouse
  2. Marathon
KCB Waterfront Split Home Walkable to Cabana Club
SUPERHOST
  1. Entire apartment
  2. Marathon
Sombrero Beach Tropical Getaway
SUPERHOST
  1. Entire townhouse
  2. Islamorada
Waterfront Townhouse in Islamorada with Boat Slip
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Manta Cottage
SUPERHOST
  1. Entire rental unit
  2. Key West
Key west in town studio with free bikes
SUPERHOST
  1. Entire apartment
  2. Key Colony Beach
Beachside Unit 07 - Come Enjoy Our Private Beach

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