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2026-11-10
2026-11-11
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Luxury accommodations in Islamorada

Fisher Inn Resort & Marina

84951 Overseas Highway, Islamorada, United States Show map

The 3-star oceanfront Fisher Inn Resort & Marina Islamorada, located just 0.8 km from Windley Key Island, offers a heated pool and Wi-Fi throughout the property. This Islamorada hotel is in a… More

From US$ 215 Book Now

Caloosa Cove Resort By Coolvacay

73801 Overseas Highway, Islamorada, United States Show map

Situated approximately a 5-minute walk from a beach, Caloosa Cove Resort By Coolvacay Islamorada offers rooms with views of the ocean. Featuring a private beach area and a convenience store, this 3… More

From US$ 414 Book Now

Pines & Palms Resort

80401 Old Highway, Islamorada, United States Show map

Pines & Palms Resort Islamorada enjoys a private location and provides easy access to Lobster Trap Art Gift Shop and Gallery 3 km away. Featuring 24 rooms with views of the sea, this resort is a 15… More

From US$ 508 Book Now

Matecumbe Resort

76261 Overseas Highway, Islamorada, United States Show map

Situated right near Lower Matecumbe Key Island, the comfortable Matecumbe Resort Islamorada offers a sunbathing terrace and a picnic area. Featuring a private beach area and luggage storage, the 2… More

From US$ 125 Book Now

Cheeca Lodge & Spa

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

Proudly offering 10 outdoor tennis courts, the exclusive 5-star Cheeca Lodge & Spa Islamorada hotel stands only 1.4 km from Lignumvitae Key Botanical State Park. Nestled right near Michelle Nicole… More

From US$ 185 Book Now

Hadley Resort And Marina

82749 Overseas Highway, Islamorada, United States Show map

Located only a 13-minute stroll from Lobster Trap Art Gift Shop and Gallery, the charming 3-star Hadley Resort And Marina Islamorada offers Wi-Fi throughout the property and a car park. Boasting an… More

From US$ 147 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

Offering a sunbathing terrace, playground, and a golf course, the 4-star Amara Cay Resort Islamorada is situated in Islamorada, about 3 km from Upper Matecumbe Key Island. The resort lies 10 minutes'… More

From US$ 266 Book Now

The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

Located in the beach area of Islamorada, the comfortable 5-star The Islands Of Islamorada hotel offers air-conditioned rooms with tea and coffee making equipment. This Islamorada hotel is in a… More

From US$ 945 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Situated around 5 minutes' walk from a beach, the 5-star boutique-style Casa Morada Hotel Islamorada offers rooms with views of the patio. Offering snorkelling, kayaking, and boating in the area… More

From US$ 720 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

Located 3.1 km from Lobster Trap Art Gift Shop and Gallery, the 4-star La Siesta Resort & Villas Islamorada offers air-conditioned rooms nearly a 25-minute walk from Gallery Morada. This Islamorada… More

From US$ 232 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

Offering a sundeck, a veranda, and grill, as well as the views of the sea, the 4-star Islander Resort Islamorada is located approximately a 20-minute walk from Indian Key State Historic Site. The… More

From US$ 300 Book Now

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

84457 Overseas Highway, Islamorada, United States Show map

Offering a restaurant, the 4-star Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort lies in the cultural district of Islamorada, approximately 10 minutes by car from the world… More

From US$ 180 Book Now

Breezy Palms Resort

80015 Overseas Highway, Islamorada, United States Show map

The comfortable 3-star Breezy Palms Resort Islamorada, located only 1.4 km from Lignumvitae Key Botanical State Park, offers an outdoor swimming pool, Wi-Fi throughout the property. This Islamorada… More

From US$ 142 Book Now

The Ocean View Inn

84500 Overseas Highway, Islamorada, United States Show map

The Ocean View Inn Islamorada offers air-conditioned rooms within a 700-metre distance of Windley Key Fossil Reef Geological State Park. In addition to a car park, the hotel offers stunning views of… More

From US$ 226 Book Now

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

The 3-star Chesapeake Beach Resort Islamorada offers air-conditioned rooms about a 10-minute walk from Wilson Key. Located around 5 km from Rain Barrel Sculpture Gallery, the hotel offers views of… More

From US$ 149 Book Now

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

The 4-star luxurious Bayside Villas By Islander Resort Islamorada sits just 7 minutes' walk from Lignumvitae Key Botanical State Park and offers a restaurant. Boasting access to History of Diving… More

From US$ 191 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

The comfortable 3-star Sunset Inn Islamorada is approximately 700 metres from Islander resort and offers a year-round outdoor swimming pool. The inn is a good starting point for exploring Islamorada,… More

From US$ 107 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

The 3-star oceanfront Drop Anchor Resort & Marina Islamorada is located merely 100 metres from Windley Key Fossil Reef Geological State Park, offering 18 rooms, Wi-Fi, and parking. Boasting a heated… More

From US$ 343 Book Now

Treasure Harbor

200 Treasure Harbor Drive, Islamorada, United States Show map

Situated only 5 minutes on foot from Rain Barrel Sculpture Gallery, the comfortable 3-star Treasure Harbor Hotel Islamorada offers comfortable rooms, Wi-Fi, and a car park. Boasting an outdoor… More

From US$ 171 Book Now

Ragged Edge Resort & Marina

243 Treasure Harbor Drive, Islamorada, United States Show map

Located merely 0.9 km from Windley Key, the comfortable Ragged Edge Resort & Marina Islamorada offers air-conditioned rooms about 10 minutes' walk from Bluewater In The Keys. Offering views of the… More

From US$ 233 Book Now

Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway, Islamorada, United States Show map

Located only steps away from Lower Matecumbe Key Island, Key Lime Cottage In The Heart Of Islamorada is suitable for 5 guests and provides a heated pool to relax in. Located a 25-minute walk from… More

From US$ 326 Book Now

Anglers Reef Vacation Rental

109 Anglers Way, Islamorada, United States Show map

At the 2-bedroom Anglers Reef Vacation Rental Islamorada villa, guests can enjoy canyoning, cycling, and fisheries as well as a location approximately 5 minutes' walk from Windley Key Fossil Reef… More

From US$ 365 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

The 2-bedroom Margaritaville Islamorada villa accommodates up to 6 guests and offers proximity to Islamorada, located merely a 10-minute walk away. More

Book Now

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

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

Situated just 500 metres from Windley Key Fossil Reef Geological State Park, the 3-bedroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is suitable for 6 guests and provides… More

From US$ 467 Book Now

Pineapple Beach - Luxury 5Br Oceanfront Estate With Heated Pool & Private Dock

130 Aregood Lane, Islamorada, United States Show map

During the stay at Pineapple Beach Islamorada villa, guests can indulge in cycling and fisheries or visit Rain Barrel Village, located 2.5 km away. Featuring a Jacuzzi, the 5-bedroom holiday home is… More

From US$ 2875 Book Now

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

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

Situated just 9 minutes' stroll from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is suitable… More

From US$ 1360 Book Now

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

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

Staying at the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa, guests can visit Indian Key State Historic Site, which is nearly a 25-minute walk away.… More

From US$ 590 Book Now

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

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

Located 9 minutes' walk from Lobster Trap Art Gift Shop and Gallery, Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is suitable for 6 guests and provides a… More

From US$ 722 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Situated only 0.7 km from Windley Key Fossil Reef Geological State Park, the 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is ideal for up to 7 guests. Providing guests… More

From US$ 624 Book Now

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

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

The 3-bedroom Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa accommodates up to 8 guests and offers proximity to Windley Key Fossil Reef Geological… More

From US$ 723 Book Now

Pristine Islamorada Pool Home With Ocean View And Dockage

148 Anglers Way, Islamorada, United States Show map

Located only 5 minutes' walk from Windley Key Fossil Reef Geological State Park, the 2-bedroom Pristine Islamorada Pool Home With Ocean View And Dockage boasts an outdoor swimming pool and can… More

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

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

Along with proximity to Lobster Trap Art Gift Shop and Gallery, located only 9 minutes' stroll away, the 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location… More

From US$ 1071 Book Now

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Located just 0.7 km from Rain Barrel Village, the 2-room Executive Bay Islamorada By Sofla Vacations villa offers opportunities for snorkelling, diving, and fisheries in the area. This Islamorada… More

From US$ 150 Book Now

Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9

135 Gulfview Drive, Islamorada, United States Show map

Staying at Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9 Islamorada, guests can visit Craig Key Island, which is approximately a 10-minute ride away. More

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Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

Located just a 7-minute walk from Indian Key State Historic Site, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa invites guests to enjoy a Jacuzzi. Located fairly close to FNX… More

Book Now

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

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

Located 750 metres from Lobster Trap Art Gift Shop and Gallery, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa is suitable for 6 guests and provides an outdoor… More

From US$ 1093 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

Along with proximity to Windley Key Fossil Reef Geological State Park, a mere 0.6 km away, the 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool… More

From US$ 394 Book Now

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

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

Located just a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa features a heated… More

From US$ 587 Book Now