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2026-09-15
2026-09-16
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Unrated hotels in Islamorada

Oceanside Anglers Reef Home With Beach Pool And Kayaks

119 Anglers Way, Islamorada, United States Show map

Situated around a 5-minute walk from Windley Key Fossil Reef Geological State Park, Oceanside Anglers Reef Home With Beach Pool And Kayaks Islamorada entices guests with fishing in the area. More

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Sandglass 4

74980 Overseas Hwy 4, Islamorada, United States Show map

Situated about 15 minutes' walk from the Lower Matecumbe Key, the 5-bedroom Sandglass 4 Islamorada villa provides access to numerous tourist attractions in the area. Suitable for up to 12 guests, the… More

From US$ 696 Book Now

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada hosts up to 12 guests and provides proximity to the Lower Matecumbe Key, situated only a 5-minute stroll away. Guests can… More

From US$ 1939 Book Now

Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #1, Islamorada, United States Show map

Featuring a year-round outdoor swimming pool for guests' relaxation, Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is located nearly 25 minutes' walk from the… More

From US$ 957 Book Now

Fl Keys Venetian Shores Waterfront With Ocean Access, Pool

141 Stromboli Drive, Islamorada, United States Show map

Located approximately 25 minutes' walk from the 45-acre Founders Park, Fl Keys Venetian Shores Waterfront With Ocean Access, Pool Islamorada villa has a swimming pool and is ideal for up to 8 guests.… More

From US$ 1011 Book Now

Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub

101 Gulfview Dr Apt 202, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the spacious Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub, which is nearly a 15-minute walk from Anne's Beach and 3.5 km from the… More

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Palms 309

79901 Overseas Hwy., Islamorada, United States Show map

Palms 309 Villa Islamorada enjoys a beachfront location, a 10-minute drive from the Lobster Trap Art Gift Shop and Gallery, and offers guests to unwind in a hot tub. Guests can enjoy snorkelling… More

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Sirens Cove - Ocean Views, Game Room, Pool And Dock Access

84745 Old Hwy, Islamorada, United States Show map

Along with proximity to Windley Key Fossil Reef Geological State Park, located only an 8-minute stroll away, Sirens Cove - Ocean Views, Game Room, Pool And Dock Access Islamorada villa provides… More

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Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Accommodating up to 3 guests, the 1-bedroom Sunshine Place Islamorada villa is situated 3.8 km from renowned cultural sites such as the Rain Barrel Sculpture Gallery. The property features… More

From US$ 384 Book Now

Beacon Reef 307

83201 Old Hwy #307, Islamorada, United States Show map

Located about a 5-minute walk from the History of Diving Museum, the 2-bedroom Beacon Reef 307 Villa Islamorada is suitable for 4 guests and provides a Jacuzzi for a truly relaxing stay. Guests can… More

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Mirage - Islamorada Oceanfront Community, 3Br, Near Sandbar, Pool

84745 Old Hwy #13, Islamorada, United States Show map

Featuring a fitness room for active guests, Mirage - Islamorada Oceanfront Community, 3Br, Near Sandbar, Pool villa is 600 metres from the Windley Key Fossil Reef Geological State Park. Guests can… More

From US$ 727 Book Now

Is39Flr Tollgate Tides

205 Tollgate Blvd, Islamorada, United States Show map

Is39Flr Tollgate Tides Villa Islamorada entices active guests with access to a fitness club and is located around a 5-minute stroll from Anne's Beach. More

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Private Beach Heated Pool Volleyball Court Orchid Beach Key

77145 Overseas Hwy, Islamorada, United States Show map

During the stay at Private Beach Heated Pool Volleyball Court Orchid Beach Key Islamorada villa, guests can indulge in snorkelling or visit the Lower Matecumbe Key, located about a 25-minute walk… More

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Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

82236 Overseas Highway, Islamorada, United States Show map

During the stay at Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa, guests can indulge in fishing or visit the Indian Key State Historic Site, located 25 minutes' walk away. Located 2.2 km… More

From US$ 1005 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Hosting up to 9 guests, Bella Villa Islamorada is nestled in a business area, about 15 minutes' walk from the Windley Key Fossil Reef Geological State Park. Guests can enjoy bowling and pool at the… More

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Florida Keys Boat Charters

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 324 Book Now

Luxury 3Br Coastal Escape In Islamorada

80639 Old Highway, Apt 309, Islamorada, United States Show map

Luxury 3Br Coastal Escape In Islamorada apartment is 17 minutes' walk from Gallery Morada and provides spa facilities such as a hot tub and a sauna. Staying in this apartment, nestled within a few… More

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Waterfront Ocean Access Canal Kamp Key Homes

76412 Overseas Highway, Islamorada, United States Show map

Waterfront Ocean Access Canal Kamp Key Homes Islamorada is nestled just around the corner from the Lower Matecumbe Key and can accommodate up to 6 guests. Guests can enjoy snorkelling at the 3… More

From US$ 450 Book Now

Is17Flr Executive Bay Club Condo M-1

87200 Overseas Highway Unit M-1, Islamorada, United States Show map

At Is17Flr Executive Bay Club Condo M-1 Islamorada villa, guests can enjoy fishing as well as a location only 10 minutes' walk from the Rain Barrel Sculpture Gallery. More

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Palms 407

79901 Overseas Hwy Unit 407, Islamorada, United States Show map

Situated within 6 km of the History of Diving Museum, the 2-bedroom Palms 407 Villa Islamorada boasts a Jacuzzi, as well as a spa salon for guests to relax in. At this Islamorada holiday home… More

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Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

Featuring an indoor water park and a wellness centre, the 6-bedroom Little Bay Compound Villa Islamorada offers guests to enjoy a beachfront location only 10 minutes' walk from the Keys History &… More

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West Plaza Del Lago

63 W Plaza Del Lago, Islamorada, United States Show map

During the stay at West Plaza Del Lago Islamorada villa, guests can indulge in windsurfing, snorkelling, and diving or visit the Lower Matecumbe Key, located a 25-minute walk away. More

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Off The Charts-Waterfront Tiki Bar & Private Dock

110 Madeira Road, Islamorada, United States Show map

Staying at the 3-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada, guests can visit the Hurricane Monument, which is a mere 14 minutes' stroll away. The Islamorada villa is… More

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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Ave Unit #5, Islamorada, United States Show map

The 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is located a mere 1.2 km from the Upper Matecumbe Key, giving access to various tourist… More

From US$ 605 Book Now

Beacon Reef 222

83201 Old Highway Unit 222, Islamorada, United States Show map

Situated 300 m from the History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada is ideal for up to 4 guests. This 2-bathroom villa features opportunities for snorkelling in the area,… More

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Little Bay Lower

82246 Overseas Hwy, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the 2-room Little Bay Lower Islamorada apartment, which is 2.2 km from the Lignumvitae Key Botanical State Park and merely 12 minutes' walk from the… More

From US$ 621 Book Now

Island Time - Oceanview Balconies- Dock- Htd Pool

84745 Old Hwy #12, Islamorada, United States Show map

Situated just 8 minutes on foot from the Windley Key Fossil Reef Geological State Park, the 3-bedroom Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada ensures a great leisure… More

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Snorkel In Islamorada'S Clear Blue Waters

85920 Overseas Highway, Islamorada, United States Show map

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The Oasis

82703 Old Highway, Islamorada, United States Show map

Hosting up to 8 guests, The Oasis Villa Islamorada is nestled in a beach area, only 1.7 km from Anne s Beach. Guests can enjoy snorkelling, canoeing, and cycling at this 3-bedroom villa, located 10… More

From US$ 1964 Book Now

Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One

101 Gulfview Drive Apt 314 Building D, Islamorada, United States Show map

The spacious 325 m² Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One Islamorada is located in Islamorada, around a 25-minute stroll from the Lower Matecumbe Key… More

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Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Ave Unit #6, Islamorada, United States Show map

Situated 7 km from the Rain Barrel Village, Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to explore various tourist attractions in the… More

From US$ 872 Book Now

Beacon Reef #204

83201 Old Highway, Islamorada, United States Show map

The 118 m² Beacon Reef #204 Apartment Islamorada is nestled in a beach area of Islamorada, about 10 minutes by car from the Windley Key Fossil Reef Geological State Park and 2.7 km from the Gallery… More

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Tea Table Key

79775 Overseas Highway, Islamorada, United States Show map

Tea Table Key Villa Islamorada offers proximity to nearby tourist spots, such as Anne s Beach, situated about 10 minutes' drive away. This Islamorada villa offers guests a relaxing experience with a… More

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Is12Flr Paradise Beach

245 Sunset Dr, Islamorada, United States Show map

Located 3 km from the Lower Matecumbe Key, Is12Flr Paradise Beach Islamorada villa gives access to various tourist sites in the vicinity. More

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Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida

10610 San Remo Dr, Islamorada, United States Show map

The 3-bedroom Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida is located about a 20-minute stroll from the 45-acre Founders Park and allows guests to enjoy diving… More

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Beacon Reef 306

83201 Old Hwy Unit 306, Islamorada, United States Show map

Located around 300 metres from the History of Diving Museum, the 2-bedroom Beacon Reef 306 Villa Islamorada is suitable for 4 guests and offers a Jacuzzi to relax in. Offering Wi-Fi, this Islamorada… More

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Islamorada Oceanfront Luxury Living

87851 Old Highway, Apt M44, Islamorada, United States Show map

Islamorada Oceanfront Luxury Living apartment is situated around 20 minutes' walk from the Rain Barrel Sculpture Gallery and offers a yoga club. Accessible to guests, this apartment offers a spa… More

From US$ 462 Book Now

Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Featuring a hot tub, the 4-bedroom Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is located merely 7 minutes' walk from the Hurricane Monument and can host up to 7 guests. Providing… More

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Palms 301

79901 Overseas Hwy Unit 301, Islamorada, United States Show map

During the stay at the 2-bedroom Palms 301 Villa Islamorada, guests can indulge in a Jacuzzi or visit the Lignumvitae Key Botanical State Park, located about 20 minutes' walk away. This 2-bathroom… More

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Straight To The Islamorada Sandbar Charters

85920 Overseas Highway, Islamorada, United States Show map

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Palms 313

79901 Overseas Hwy Unit 313, Islamorada, United States Show map

Situated about a 10-minute drive from the class museum "Florida Keys History and Discovery Center", Palms 313 Villa Islamorada boasts a Jacuzzi, as well as a spa salon for guests to relax in. At this… More

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Beacon Reef 310

83201 Old Highway #310, Islamorada, United States Show map

Offering guests to unwind in a Jacuzzi, Beacon Reef 310 Villa Islamorada is located 25 minutes' walk from the Upper Matecumbe Key. Guests can enjoy windsurfing, snorkelling, and canoeing at the 2… More

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Florida Keys Boat Trips Multi Activity

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 342 Book Now

Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two

101 Gulfview Drive Apt #D316 Building D, Islamorada, United States Show map

The spacious 188 m² Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two Islamorada apartment is a good choice for accommodating up to 6 guests, offering a convenient… More

From US$ 1446 Book Now

Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key

101 Gulfview Drive Apt 314-316, Islamorada, United States Show map

Located 25 minutes' walk from the Lower Matecumbe Key, the spacious Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada overlooks the sea. Boasting a… More

From US$ 1899 Book Now

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool

84745 Old Hwy #14, Islamorada, United States Show map

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa accommodates up to 6 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located merely an 8… More

From US$ 1403 Book Now