Holiday Rentals in Islamorada
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5 km
744 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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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New Rental! Beautiful canal pool home with dockage!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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You will never want to leave
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Islamorada house with waterfront, private dock and beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3 BR 2 Bath Islamorada home with Private Beach Access
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mini Ray's of Sunshine
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This is The Oasis, YOUR private Oasis!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Bonefish House at Tarpon Point
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This studio makes the best of the space
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
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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Beautiful 3 Bedroom Condo - Bay Harbour A101
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 2 Bedroom House with Peekaboo Views
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Oceanfront Oasis in Angler’s Reef with Private Boat Slip
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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" Endless Summer" Awaits!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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La Casita White Marlin
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A True Islamorada Oasis with Breathtaking Bay Views
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Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
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Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanview 2b/2b w/ Boatslip
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Discover the Charm of Island Living
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Beautiful vacation home in the heart of Islamorada , Florida Keys
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock
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Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 Bedroom Private Oceanfront House - Sol
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Little Piece of Paradise (AVAIL Oct-Dec)
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxurious Caribbean 2 Bedroom 2 Bath Home
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Maison Matecumbe.... the heart of Islamorada!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Keys Getaway - A
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Condo/Apartment
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sun, Ocean and a Luxury Oasis with a discount Flexible stays contact host
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful oceanfront resort located at mile marker 73.8
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 744
Frequently Asked Questions about Islamorada
- Yes, here are some popular holiday rentals in Islamorada that have a pool:
- Ocean Front Town House With Breath Taking Views From all 3 Balconies
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Yes, here are some popular holiday rentals in Islamorada that have internet access:
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
- The best pet friendly rentals in Islamorada are:
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
- Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
- Some of the most popular kid friendly rentals in Islamorada are:
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
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