Holiday Rentals in Islamorada
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
855 rentals in Islamorada.
Lovely Islamorada Studio in the Heart of the Keys
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Islamorada Waterfront Paradise Getaway!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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�AQUAMARINE OCEANVIEW�FLASH⚡️SALE+DOCK+TENNIS+POOL+SPA+GYM+⭐️BEST REVIEWS
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SEP/OCT reduced 3BR 2.5BA OceanFRONT Wide Ocean Views Huge Decks Yaks/SUPs Dock
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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OCEANFRONT ANGLERS REEF LUXURY HOME- Pool, Dock, Beach, Kayaks, Paddle Boards
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Renovated - Boat slip, pool, beach - Anglers Reef oceanside gated community
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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GREAT LOCATION !!! White Marlin Beach House, Islamorada
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beach Dream House, relax and enjoy the clear waters of Islamorada FL
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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☀️Luxury 3 BR Remodeled! Ocean View, Pool Spa, Marina Bikes Kayak Tennis/Pickle
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Tiki Bar,Heat&Chill Pool,Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV,
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 'Keysey' Condo in Gated Community (VR-196)
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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A little Piece of Heaven to wash your worries away
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southern Diversion Estate Islamorada
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Keys Cottage; Remodeled Villa in Native Hammock on Florida Bay
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BAYSIDE PARADISE ~ Heart of Islamorada *Private Boat Dockage Upon Request*
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Location. Location. Location.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pool | Sunsets | Walk to restaurants | Little Basin Villas | Key Lime Villa 3
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Star Modern Oceanfront Islamorada Townhome on the Beach!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef- Book Spring Break and Summer Now!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Brand New / Totally Renovated Luxurious Home New To Rental Market.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation Condo at Futura Yacht Club
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury villa with beautiful bay views | Pool | Little Basin Villas | Bay Villa 9
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Private Bayside Waterfront Home 4 acres, Private Beach, Deep Water Boat Dock
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 855
Frequently Asked Questions about Islamorada
- Yes, here are some popular holiday rentals in Islamorada that have a pool:
- Newly refinished condo open water views very nice
- Come relax in Islamorada, the tropical jewel of the Florida Keys!!
- 5th Floor Oceanfront Corner Condo, Views, Pool, Wi-Fi
- Yes, here are some popular holiday rentals in Islamorada that have internet access:
- Newly refinished condo open water views very nice
- Come relax in Islamorada, the tropical jewel of the Florida Keys!!
- 5th Floor Oceanfront Corner Condo, Views, Pool, Wi-Fi
- Some of the most popular kid friendly rentals in Islamorada are:
- Newly refinished condo open water views very nice
- Come relax in Islamorada, the tropical jewel of the Florida Keys!!
- 5th Floor Oceanfront Corner Condo, Views, Pool, Wi-Fi