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Islamorada Vacation Rentals in the Florida Keys

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Islamorada, Florida.

Vacation Rentals - Islamorada Townhome

Beautiful Townhouse in the heart of the Florida Keys

SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Keys. Amazing sunset, great community pool and beach. Next to founders park with many amenities that can be used when staying at this home away from home. Boat access, slips and marina. Great pier for fishing and watching the best s.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 10 Townhome Rentals

Vacation Home

Vacation Rentals - Islamorada House

Beautiful centrally located home in the Florida keys.

Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in your private dock with 35 feet of dockage.Minutes to the bay and very easy access to the ocean.There is access to a private homeowners beach with Cabañas and outdoor charcoal bbq.The home has 3 bedrooms and two bathrooms upstair.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Vacation Rentals - Islamorada House

Beautiful 2/2 Florida keys home rental

Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with private beach , golf cart allowed on public road ,community access to private boat ramp. Will rent 3 month minimum to snowbirds From the month of November through April .Preferably to adults with no children and no pets. Access to 25'.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Pelican 1x1KingBed - Islamorada Hotel

Explore the Outdoors! Free Parking, Minutes to Fishing, Snorkeling & State Parks

This beachfront property is a laid-back spot for your Keys getaway! Relax on the private beach, take a dip in the oceanfront pool, or enjoy a refreshing drink or afternoon snack at the poolside cafe. Guests can explore the local area and the property’s sister resorts on the complimentary shuttle. The property also features an on-site marina, and .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

Pelican 1x1KingBed - Islamorada Hotel

Welcome to this Hidden Gem in the Keys! Private Beach, Outdoor Pool, Restaurant

This beachfront property is a laid-back spot for your Keys getaway! Relax on the private beach, take a dip in the oceanfront pool, or enjoy a refreshing drink or afternoon snack at the poolside cafe. Guests can explore the local area and the property’s sister resorts on the complimentary shuttle. The property also features an on-site marina, and .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

Sandy Pointe Villa - Islamorada House

New Listing!! ~ Beachfront Islamorada Villa with Dockage & Bay Views

The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, a private sandy beach and protected dockage, canal-side. This duplex features 3 bedrooms and 3 baths with an open layout for a spacious kitchen and dining room, and a living room with wall to wall sliding glass doors giving yo.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Anglers Way Villa I - Islamorada House

End of Summer Paradise at Anglers Reef

2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious villa, one of the biggest 2 bedroom villas in the community. C.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Tropical Oceanfront views - Studio!!!! - Islamorada Condo

Tropical Oceanfront views - Studio!!!!

Caloosa Cove Resort and Marina offers a variety of amenities, onsite and close by, a heated swimming pool and beach area, Safari Lounge, General Store, free Wi-Fi, and Charter Boats, plus a wide selection of activities! Located on the Majestic Islamorada, Florida Keys this updated oceanfront Studio Suite includes a queen-size bed, twin sleeper sofa.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 3 Condo Rentals

Vacation Home

Vacation Rentals - Islamorada Townhome

Beautiful townhome directly on the water

This stunning home is located at an exclusive sought out gated neighborhood in Islamorada, Florida. Located directly on the Bay with completely unobstructed views of the ocean. Home is meticulously decorates, with Beach House Chic decor. Home offers one master bedroom , second bedroom has two bunk beds , a loft that offers one queen size bed and pu.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Townhome Rentals

Vacation Home

Islamorada Paradise! - Islamorada Townhome

Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)

(6 month minimum rental) - $3,100 per month (without boat slip). Slip an additional $300 a month. Situated on a quiet street in Port Antigua, unwind in this fully renovated 3-story townhouse. The unique three story layout has a large entertainment living area with a half-bath, pool table, bar and living area and two terraces on the first floor, a .......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

Vacation Rentals - Islamorada House

Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach

*****New Owners/Listing so you may not see reviews yet for that reason****** ***** Please email and I will answer any questions you have!***** Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home has endless views of the ocean from every room. If you enjoy watching the.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Summer Sea 320 - Islamorada Condo

Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada

Premier 1 bedroom unit with both that stunning bay view and a view of the pool off the balcony. Fully updated with the open concept kitchen open to the diving and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops through out the apartment. Comfortable queen size bed with a pull out couch in the livingroom.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Radiant Suite with Ocean View and Resort Amenities - Islamorada Hotel

Radiant Suite with Ocean View and Resort Amenities

WELCOME TO THE ISLANDS OF ISLAMORADA Designed for those who love the bounty and beauty of the ocean, The Islands of Islamorada seamlessly weaves the allure of tropical beauty with familiar luxurious comforts, creating a captivating experience for the whole family. Spend meaningful time in this natural haven, and relax in privacy among family and fr.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Hotel Rentals

Vacation Home

Casa Dos Hondos - Islamorada House

Desirable Anglers Reef Villa (133) in Islamorada w/Optional On-Site Boat Slip

Welcome to paradise! "Casa Dos Hondos" is an immaculately clean, single family, Key West style home located in the desirable gated, resort community of Anglers Reef in Islamorada. The grounds, waterfront and amenities are spectacular, featuring a private heated pool on the coast of the Atlantic Ocean overlooking the Straits of Florida, two privat.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 4 House Rentals

Vacation Home

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