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2026-08-01
2026-08-02
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Luxury accommodations in Islamorada

Fisher Inn Resort & Marina

84951 Overseas Highway, Islamorada, United States Show map

Located about a 15-minute walk from Whale Harbor, Fisher Inn Resort & Marina Islamorada offers access to a private beach fitted with umbrellas and beach towels. This hotel features an outdoor… More

From US$ 215 Book Now

Caloosa Cove Resort By Coolvacay

73801 Overseas Highway, Islamorada, United States Show map

The 3-star Caloosa Cove Resort By Coolvacay Islamorada is within 5 minutes' walk of Anne's Beach, offering a vending machine and a lift for guests' utmost comfort. Located 3.1 km from the Lower… More

From US$ 414 Book Now

Matecumbe Resort

76261 Overseas Highway, Islamorada, United States Show map

Matecumbe Resort Islamorada offers air-conditioned rooms a few steps from the Lower Matecumbe Key. The aparthotel offers Wi-Fi in public areas, parking on site and a year-round outdoor pool. More

From US$ 125 Book Now

Cheeca Lodge & Spa

81801 Overseas Highway Mile Marker 82, Islamorada, United States Show map

Offering a gift shop and a restaurant, the luxury Cheeca Lodge & Spa Islamorada hotel lies in the cultural district of Islamorada, just 100 m from the Matecumbe United Methodist Church and 16… More

From US$ 185 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

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

The comfortable Amara Cay Resort Islamorada offers access to the Upper Matecumbe Key, which is located around 3 km away. The 4-star beachfront hotel has a heated swimming pool along with a tiki bar… More

From US$ 266 Book Now

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

Pines & Palms Resort

80401 Old Highway, Islamorada, United States Show map

Located about 20 minutes' walk from The Hok, the 3-star Pines & Palms Resort Islamorada offers access to a private beach fitted with beach umbrellas and beach towels. Featuring 24 rooms with views of… More

From US$ 134 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

Located merely 1.2 km from the Indian Key State Historic Site, the 4-star beachfront La Siesta Resort & Villas Islamorada offers amenities such as various recreational opportunities and watersports… More

From US$ 232 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Boasting the chance to relax by Barley Basin, situated approximately a 20-minute stroll away, the comfortable 5-star Casa Morada Hotel Islamorada also invites guests to go fishing. Featuring a heated… More

From US$ 464 Book Now

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort

84457 Overseas Highway, Islamorada, United States Show map

The charming 4-star Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort, located just 1.2 km from the Windley Key Fossil Reef Geological State Park, offers 3 outdoor swimming pools… More

From US$ 180 Book Now

Breezy Palms Resort

80015 Overseas Highway, Islamorada, United States Show map

Featuring views of the pool, the 3-star Breezy Palms Resort Islamorada lies in a beach area, 17 minutes' walk from the Lignumvitae Key Botanical State Park. Offering 54 rooms, the resort provides an… More

From US$ 142 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

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

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

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

The contemporary 4-star Bayside Villas By Islander Resort Islamorada is situated only 600 metres from the Indian Key State Historic Site and boasts a sun deck and a picnic area. Boasting a heated… More

From US$ 191 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

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

Treasure Harbor

200 Treasure Harbor Drive, Islamorada, United States Show map

The 3-star Treasure Harbor Hotel Islamorada offers its guests comfortable rooms a mere 5 minutes' walk from the Rain Barrel Village. This comfortable hotel also includes a car park. More

From US$ 171 Book Now

Ragged Edge Resort & Marina

243 Treasure Harbor Drive, Islamorada, United States Show map

Located approximately 10 minutes on foot from Bluewater In The Keys, the comfortable Ragged Edge Resort & Marina Islamorada features Wi-Fi throughout the property and a private parking lot on site. More

From US$ 360 Book Now

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

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

Providing guests with a wellness centre and a year-round outdoor swimming pool to ensure a memorable stay, the 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! More

From US$ 1093 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

Margaritaville Islamorada villa is located 25 minutes' walk from the 45 - acre Founders Park and invites guests to enjoy a terrace. The 2-bedroom holiday home hosts up to 6 guests and provides them… More

Book Now

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Offering sea views, Executive Bay Islamorada By Sofla Vacations villa is situated only 0.7 km from the Rain Barrel Sculpture Gallery. This 8-room holiday home features opportunities for snorkelling… More

From US$ 150 Book Now

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

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

Located merely a 7-minute walk from the Windley Key Fossil Reef Geological State Park, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers snorkelling, ping pong, and… More

From US$ 467 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 2-bedroom villa features opportunities for canoeing… More

From US$ 365 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Offering sea views, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is situated 650 metres from the Windley Key Fossil Reef Geological State Park. The 3-bedroom holiday home hosts… More

From US$ 624 Book Now

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

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

The 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa hosts up to 6 guests and provides proximity to the Lobster Trap Art Gift Shop and Gallery… More

From US$ 896 Book Now

Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway, Islamorada, United States Show map

Located right around the corner from the Lower Matecumbe Key, 2-bedroom Key Lime Cottage In The Heart Of Islamorada boasts a heated pool and can accommodate up to 5. Providing guests with Wi-Fi and… More

From US$ 681 Book Now

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

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

Situated just 500 m from the class museum "Florida Keys History and Discovery Center", the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is… More

From US$ 1360 Book Now

Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

Located approximately 5 minutes' walk from FNX Club by Islamorada Fitness, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa gives easy access to various tourist attractions in the… More

Book Now

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

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

Offering a location about 15 minutes' walk from Anne s Beach, the 3-bedroom Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa gives access to various tourist… More

From US$ 722 Book Now

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

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

Offering karaoke for a delightful experience, Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa is located within a 700-metre distance of the Windley… More

From US$ 723 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

Offering live performances for a delightful experience, Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina is located just an 8-minute… More

From US$ 394 Book Now

Pineapple Beach

130 Aregood Lane, Islamorada, United States Show map

Located 2.5 km from the Rain Barrel Sculpture Gallery, Pineapple Beach Islamorada villa features a private swimming pool, a hot tub, ensuring a relaxing stay. More

From US$ 2875 Book Now

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

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

The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa accommodates up to 6 guests and offers proximity to the Lobster Trap Art Gift Shop and Gallery… 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

Situated just 1 km from the Michelle Nicole Lowe Art Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to explore… More

From US$ 587 Book Now