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2026-07-25
2026-07-26
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Hotels in Islamorada area of Florida Keys

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

The oceanfront Chesapeake Beach Resort Islamorada enjoys a private location about 5 minutes' walk from the Whale Harbor Marina and offers 45 rooms with views of the pool. Featuring a heated pool, the… More

From US$ 149 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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Beacon Reef 501

83201 Old Highway #501, Islamorada, United States Show map

Beacon Reef 501 Villa Islamorada is situated just a 5-minute walk from the History of Diving Museum and provides a hot tub for additional comfort. Located fairly close to Island Community Church… More

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Beacon Reef 406

83201 Old Hwy Unit #406, Islamorada, United States Show map

Located about 5 minutes' walk from the History of Diving Museum, the 2-bedroom Beacon Reef 406 Villa Islamorada offers windsurfing, snorkelling, and bowling to diversify guests' leisure. Offering a… More

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Beacon Reef 503

83201 Old Highway #503, Islamorada, United States Show map

Offering a hot tub for a relaxing experience, Beacon Reef 503 Villa Islamorada is located an 18-minute walk from the class museum "Florida Keys History and Discovery Center". The 2-bedroom holiday… More

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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 entices guests with a Jacuzzi. Guests can enjoy windsurfing, snorkelling, and diving at… More

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Beacon Reef 222

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

Located 300 m from the History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada offers snorkelling to diversify guests' leisure. More

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Beacon Reef 306

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

The 2-bedroom Beacon Reef 306 Villa Islamorada is located within 5 minutes' walk of Island Community Church and offers a hot tub for guests' relaxation. At this Islamorada holiday home, located 2.6… More

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Beacon Reef 310

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

During the stay at Beacon Reef 310 Villa Islamorada, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Lobster Trap Art Gift Shop and Gallery, located 20 minutes' walk away. More

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The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

Offering a swimming pool, the 4-star The Islands Of Islamorada hotel is nestled in the cultural district of Islamorada, around a 20-minute walk from the Hurricane Monument. This comfortable hotel… More

From US$ 2000 Book Now

Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Sunshine Place Islamorada villa is located 4.2 km from the 45 - acre Founders Park and provides snorkelling, diving, and bowling for active guests. More

From US$ 384 Book Now

Hadley Resort And Marina

82749 Overseas Highway,, Islamorada, United States Show map

Offering various recreational opportunities and barbecue, the smoke-free Hadley Resort And Marina Islamorada lies in an entertainment area of Islamorada, a 19-minute walk from the Upper Matecumbe Key… More

From US$ 147 Book Now

The Oasis

82703 Old Highway, Islamorada, United States Show map

Located just 0.7 km from the History of Diving Museum, the beachfront The Oasis Villa Islamorada offers snorkelling, canoeing, and cycling to diversify guests' leisure. This 3-bedroom villa includes… More

From US$ 1964 Book Now

Little Bay Cottage

82246 Overseas Hwy, Islamorada, United States Show map

Situated approximately a 10-minute walk from the Keys History & Discovery Center, the 2-bedroom Little Bay Cottage Islamorada entices guests with snorkelling, diving, and fishing in the area. More

From US$ 549 Book Now

Little Bay Upper

82246 Overseas Hwy, Islamorada, United States Show map

Little Bay Upper Apartment Islamorada is 10 minutes' walk from the Keys History & Discovery Center and can accommodate up to 6 guests. Offering an indoor water park and a wellness centre, this… More

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Little Bay Prime

82246 Overseas Highway, Islamorada, United States Show map

The 4-room Little Bay Prime Apartment Islamorada enjoys a beachfront location around a 10-minute walk from the Keys History & Discovery Center. The maximum occupancy at this apartment is 12 guests. More

From US$ 1510 Book Now

Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

Located only 10 minutes' walk from the Keys History & Discovery Center, the beachfront Little Bay Compound Villa Islamorada offers windsurfing, snorkelling, and diving to diversify guests' leisure. 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

Paradise Palms Islamorada

84745 Old Highway Unit 9, Closest To The Ocean!, Islamorada, United States Show map

Situated 2.6 km from the History of Diving Museum, Paradise Palms Islamorada villa entices guests to explore various tourist attractions in the area. More

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Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

A1, 84745 Old Highway, Islamorada, United States Show map

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa is situated within a 700-metre distance of the Windley Key Fossil Reef Geological State Park and… More

From US$ 723 Book Now

The Ocean View Inn

84500 Overseas Highway, Islamorada, United States Show map

Featuring a restaurant, the comfortable The Ocean View Inn Islamorada lies 700 m from the Windley Key Fossil Reef Geological State Park. This 3-star hotel, overlooking Islamorada, offers an American… More

From US$ 345 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Situated 650 metres from the Windley Key Fossil Reef Geological State Park, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa offers guests to relax by a private swimming pool. More

From US$ 624 Book Now

Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

82236 Overseas Highway, Islamorada, United States Show map

Located 25 minutes' walk from the Lignumvitae Key Botanical State Park, Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa gives access to various tourist sites in the vicinity. More

From US$ 1005 Book Now

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

84745 Old Hwy #6, Islamorada, United States Show map

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is located merely a 7-minute walk from the Windley Key Fossil Reef Geological State Park and entices guests with a spa centre… More

From US$ 467 Book Now

Island Time - Oceanview Balconies- Dock- Htd Pool

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

Located just 8 minutes on foot from the Windley Key Fossil Reef Geological State Park, Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada includes a terrace with views of the sea. More

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

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

Located merely 8 minutes' walk from the Windley Key Fossil Reef Geological State Park, Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa offers opportunities for snorkelling… More

From US$ 1403 Book Now

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

84 Johnston Ave Unit #9, Islamorada, United States Show map

Located merely 6 minutes' walk from the world-class museum "Florida Keys History and Discovery Center", the 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada… More

From US$ 1093 Book Now

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

84 Johnston Ave Unit #8, Islamorada, United States Show map

Situated approximately a 15-minute walk from the Hurricane Monument, the 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to… More

From US$ 896 Book Now

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

84 Johnston Avenue Unit #4, Islamorada, United States Show map

Offering a spa centre and a play area for guests' leisure, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is situated approximately a 25… More

From US$ 1360 Book Now

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

84 Johnston Ave Unit #7, Islamorada, United States Show map

Situated nearly a 25-minute walk from the Indian Key State Historic Site, the 3-bedroom Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa provides access to… More

From US$ 722 Book Now

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #3, Islamorada, United States Show map

Situated just a 9-minute walk from the Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa offers guests to… More

From US$ 590 Book Now

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

84 Johnston Ave Unit #2, Islamorada, United States Show map

Providing guests with a spa centre and a play area to ensure a memorable stay, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is only 9… More

From US$ 587 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 pool for guests' relaxation, Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is located nearly 25 minutes' walk from the Indian… More

From US$ 957 Book Now

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

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

Staying at the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can easily reach the Upper Matecumbe Key, located a mere 1.2 km away. More

From US$ 605 Book Now

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

Coconut Cove Resort & Marina

84801 Overseas Highway, Islamorada, United States Show map

Offering air-conditioned rooms and Wi-Fi in public areas, the 2-star Coconut Cove Resort & Marina Islamorada is 10 minutes' drive from the Rain Barrel Sculpture Gallery and 3.7 km from the Islamorada… More

From US$ 245 Book Now

La Jolla Resort

82216 Overseas Highway, Islamorada, United States Show map

Featuring Wi-Fi in public areas, La Jolla Resort Islamorada sits a 14-minute walk from the History of Diving Museum. Situated in a beach area, 550 metres from an own beach, this resort offers an… More

From US$ 181 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

Offering air-conditioned rooms and Wi-Fi in public areas, the smoke-free Sunset Inn Islamorada is only 1.3 km from the Gallery Morada and merely an 11-minute walk from the Upper Matecumbe Key. More

From US$ 107 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Casa Morada Hotel Islamorada, located 5 minutes on foot from the Lobster Trap Art Gift Shop and Gallery and just 1.3 km from the History of Diving Museum, features a swimming pool for guests to take… More

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Off The Charts-Waterfront Tiki Bar & Private Dock

110 Madeira Road, Islamorada, United States Show map

Located only a 14-minute stroll from the Hurricane Monument, the 2-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada offers a terrace with views of the sea. More

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Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

The 3-bedroom Martin Family Fish Camp Villa Islamorada is located about 5 minutes' walk from the Lobster Trap Art Gift Shop and Gallery and invites guests to enjoy guided snorkelling trips. This… More

From US$ 823 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

The 3-star Drop Anchor Resort & Marina Islamorada offers air-conditioned rooms around a 20-minute walk from Wilson Key. Located 2.8 km from the Rain Barrel Sculpture Gallery, this lovely resort… More

From US$ 274 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

The 4-star luxury Islander Resort Islamorada is located within 25 minutes' walk of the Hurricane Monument and offers guided tour service for better sightseeing in Islamorada. Boasting a location a… More

From US$ 204 Book Now

Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

135 Anglers Way, Islamorada, United States Show map

Located 6 km from the Michelle Nicole Lowe Art Gallery, Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina gives access to various… More

From US$ 394 Book Now

Anglers Reef Vacation Rental

109 Anglers Way, Islamorada, United States Show map

Situated a 6-minute walk from Windley Key Island, Anglers Reef Vacation Rental Islamorada villa entices guests with views of the garden. The 3-bedroom villa features opportunities for canoeing… More

From US$ 365 Book Now

Anglers Reef Villa 1

110 Anglers Way, Islamorada, United States Show map

The 3-star Anglers Reef Villa 1 Islamorada hotel is situated within 6 km of the Hurricane Monument, which is an excellent place to improve cultural awareness. Guests can swim in a heated swimming… More

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Anglers Reef Paradise

110 Anglers Way 110, Islamorada, United States Show map

Situated about a 5-minute walk from the Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa entices guests with snorkelling, diving, and cycling in the area. More

From US$ 382 Book Now

The Caribbean Resort

117 South Carroll Street, Islamorada, United States Show map

Located in close proximity to the Keys History & Discovery Center, the 3-star smoke-free The Caribbean Resort Islamorada offers tour/ticket assistance to ensure you have an unforgettable travel… More

From US$ 550 Book Now

Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Located merely 7 minutes' walk from the Hurricane Monument, Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada provides a private swimming pool, a hot tub for additional comfort. Offering… More

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Heart Of Morada

81906 Overseas Highway #3, Islamorada, United States Show map

Situated within 20 minutes' walk of the History of Diving Museum, the 4-bedroom Heart Of Morada Villa Islamorada features a terrace with views of the sea. Offering a private swimming pool, the… More

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