Islamorada Luxury Holiday Rentals
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5 mi
808 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
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Adorable canal front Pool Home in Plantation Key
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ULTIMATE outdoor living area at this 4/4 canal home with pool!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Oceanfront Condo * Maison Matecumbe - 3 bedrooms overlooking pool, Ocean & beach
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Stunning 3 Bedroom Bayfront Home
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Breezy Happy Hours in Port Antigua Beach Home
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Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Bay View Villa in Florida Keys | Beach Getaway w/ Scenic Outdoor Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Dream House, relax and enjoy the clear waters of Islamorada FL
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Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
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Beautifully Renovated 2 Bedroom Condo
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Indulge in Home Like Comfort! Oceanfront, Free Parking, Pet-friendly Property
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Prime Location! Onsite Pool, Free Breakfast, Free Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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You will love my "Fl Keys Luxury Home"
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Islamorada� 2 private homes on open water with beach and pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
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Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Your Islamorada Vacation dream just became a reality!Â
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Paradise with surrounding beaches and amazing fishing!!!
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Great location in Islamorada, FL!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Islamorada Boaters Paradise with 70' Dock and private beach access..
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
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Safety harbor seasonal fishing getaway with room for 12
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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A little Piece of Heaven to wash your worries away
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Spacious Home in Islamorada with boat dock, private beach, & Fast
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
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Casa Del Pirata | 3 bed / 2 ba Canal Home in Islamorada
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Views for DAYS!
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Unique 2 Bedroom Bay Front Home with Roof Top Terrace
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Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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PARADISE FOUND! 3 BD townhome in BEACHFRONT Executive Bay Club in Islamorada, FL
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Princess Palm North 2 Bedrooms, 2 Baths Poolside
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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" Endless Summer" Awaits!
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3 BR 2 Bath Islamorada home with Private Beach Access
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Minutes to Library Beach Park! Onsite Parking & Outdoor Swimming Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Tropical Oasis
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OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
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Boat, Fish, Swim from Your Own 70' Dock!
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Off the beaten path in one of Islamorada’s hidden gem of a community!.
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Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10
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Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wake up in Paradise. Islamorada Florida - 6-month minimum without boat lift.
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
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Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
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