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Islamorada, FL Holiday Rentals
Holiday Rentals
USA
Florida (FL)
Florida Keys
Islamorada
Futura Yacht Club Holiday Homes
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Islamorada
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Internet or Wifi (788)
Air Conditioning (783)
Washer/Dryer (551)
Other outdoor space (548)
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Suitability
Kid friendly (772)
Pet friendly (323)
Smoking allowed (21)
Elder access (6)
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Property type
Holiday Rental House (670)
Condominium/Apartment (135)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (465)
Boat Available (85)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
History of Diving Museum
Florida Keys Brewing Company
Islamorada Brewery & Distillery - MM82
Alligator Reef Light House
Windley Key Fossil Reef Geological State Park
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805 rentals
in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Adorable canal front Pool Home in Plantation Key
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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ULTIMATE outdoor living area at this 4/4 canal home with pool!
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
2
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
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Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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" Endless Summer" Awaits!
6
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Beautiful Studio Apartment - Summer Sea Condo #230
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
10
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
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Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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RELAX in your PRIVATE Oceanfront Cottage!
21
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Peninsula Villa / Heated Pool / Sunset Point
1
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
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Deep Water Canalfront Home W/ Boat Ramp
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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New Caribbean home. Resort access to pool
2
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Free Parking
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
10
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Tranquil One Bedroom Cottage with Pool and Boat Basin
8
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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BRAND NEW HOME, pet friendly, resort location!
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 16
Match:
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Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada
1
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 8
Match:
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Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi
83
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Charming Beach Front Home in Lower Matecumbe
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Tarpon Bend ocean view with boat lifts
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 5
Match:
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All the feels... tranquility and relaxation
10
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Beautifully Renovated 2 Bedroom Oceanfront Home
2
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
61
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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New Ground Level Caribbean Cottage
3
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Charming Ocean Front Pool Home with dockage & pool
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
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Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
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The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach
2
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 8
Match:
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Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
14
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Gulf View Retreat * Bay Harbor
5
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Incredible Bayside Home in the Florida Keys!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
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Little Piece of Paradise (AVAIL Oct-Dec)
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
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Tropical retreat where location meets quintessential Keys vacation home.
1
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
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Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking
Condo/Apartment
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4 bedrooms
4 bathrooms
Sleeps 16
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Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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End of Summer Paradise at Anglers Reef
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
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Mitchell's Bayview Villa - Islamorada House on the Bay
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Your Dream Getaway at Anglers Reef
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
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Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage
3
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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