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2026-10-30
2026-10-31
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Luxury accommodations in Islamorada

Fisher Inn Resort & Marina

84951 Overseas Highway, Islamorada, United States Show map

Located 4.3 km from shopping venues such as Lobster Trap Art Gift Shop and Gallery, Fisher Inn Resort & Marina Islamorada includes luggage storage and stores. This hotel features an outdoor swimming… More

From US$ 215 Book Now

Caloosa Cove Resort By Coolvacay

73801 Overseas Highway, Islamorada, United States Show map

Situated around 5 minutes by car from Anne's Beach, the 3-star Caloosa Cove Resort By Coolvacay Islamorada offers 30 rooms. Located 3.1 km from Lower Matecumbe Key Island, this Islamorada hotel… More

From US$ 414 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 towels. The resort boasts a sun deck and a picnic area on… More

From US$ 134 Book Now

Matecumbe Resort

76261 Overseas Highway, Islamorada, United States Show map

Matecumbe Resort Islamorada offers air-conditioned rooms a few moments from Lower Matecumbe Key Island. 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

Nestled in the cultural district of Islamorada, right around the corner from Matecumbe United Methodist Church, the luxury Cheeca Lodge & Spa Islamorada hotel features an adult pool and views of the… More

From US$ 185 Book Now

Hadley Resort And Marina

82749 Overseas Highway, Islamorada, United States Show map

Offering an outdoor swimming pool, the 3-star Hadley Resort And Marina Islamorada is nestled in the entertainment district of Islamorada, a 19-minute stroll from Upper Matecumbe Key Island. Featuring… More

From US$ 147 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

Located within 3 km of Upper Matecumbe Key Island, the beachfront Amara Cay Resort Islamorada includes a sun deck, playground, and a golf course. More

From US$ 266 Book Now

The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

The 5-star The Islands Of Islamorada hotel, located in the cultural district of Islamorada, approximately a 20-minute walk from Hurricane Monument, features views of the pool. Boasting a location a… More

From US$ 721 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Situated around a 25-minute stroll from Hurricane Monument, the comfortable 5-star Casa Morada Hotel Islamorada can arrange guided snorkelling trips to ensure a more exciting holiday. Boasting a… More

From US$ 677 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

The 4-star beachfront La Siesta Resort & Villas Islamorada, located in an entertainment area, offers Wi-Fi throughout the property, an outdoor swimming pool and a fitness area. Featuring a lobby area… More

From US$ 232 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

The 4-star luxury Islander Resort Islamorada, located in a cultural neighbourhood, also stands within 25 minutes' walk of Hurricane Monument and provides guided tour service for better sightseeing. More

From US$ 204 Book Now

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

84457 Overseas Highway, Islamorada, United States Show map

Located only 1.2 km from Windley Key Fossil Reef Geological State Park, the 4-star family Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort features Wi-Fi throughout the property… 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 Lignumvitae Key Botanical State Park. Offering 54 rooms, the resort provides an… More

From US$ 142 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 merely 9 minutes' walk from Windley Key Fossil Reef Geological State Park. This 3-star hotel, overlooking Islamorada, offers… More

From US$ 213 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 Whale Harbor Marina and offers 45 rooms with views of the pool. Featuring a heated pool, the 3… More

From US$ 149 Book Now

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

Offering access to Hurricane Monument, which is only 0.9 km away, the contemporary 4-star Bayside Villas By Islander Resort Islamorada features a sundeck and a picnic area. The luxurious resort is… More

From US$ 191 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

The 3-star Sunset Inn Islamorada, located merely 5 minutes' walk from the class museum "Florida Keys History and Discovery Center" and a mere 1.3 km from Gallery Morada, features a year-round outdoor… More

From US$ 107 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

Located around a 20-minute walk from Wilson Key, the 3-star Drop Anchor Resort & Marina Islamorada boasts a heated pool. Featuring 18 rooms with views of the sea, the resort is 2.8 km from Rain… More

From US$ 343 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 only 5 minutes' walk from 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

The comfortable Ragged Edge Resort & Marina Islamorada is situated only 10 minutes on foot from Rain Barrel Village and boasts a sunbathing terrace and a picnic area. Featuring an outdoor swimming… More

From US$ 233 Book Now

Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway, Islamorada, United States Show map

Located just near Lower Matecumbe Key Island, 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 parking, this… More

From US$ 326 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 canyoning… More

From US$ 365 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

Up to 6 guests can stay at Margaritaville Islamorada villa and enjoy Cowpens Anchorage, located a 6-minute walk away. More

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

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

Located 500 metres from Windley Key Fossil Reef Geological State Park, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is suitable for 6 guests and provides a year-round… More

From US$ 467 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Located 8 minutes' stroll from Windley Key Fossil Reef Geological State Park, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is suitable for 7 guests and provides a heated pool to… 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

Located nearly a 15-minute walk from Hurricane Monument, the 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa gives access to various tourist… More

From US$ 1071 Book Now

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Featuring an outdoor swimming pool as well as views of the sea, Executive Bay Islamorada By Sofla Vacations villa offers a prime location a mere 10 minutes' walk from Rain Barrel Sculpture Gallery. More

From US$ 150 Book Now

Pristine Islamorada Pool Home With Ocean View And Dockage

148 Anglers Way, Islamorada, United States Show map

Situated nearly 5 minutes' walk from Windley Key Fossil Reef Geological State Park, the 2-bedroom Pristine Islamorada Pool Home With Ocean View And Dockage is ideal for up to 7 guests. More

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

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

Located only a 6-minute walk from the world-class museum "Florida Keys History and Discovery Center", the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location… More

From US$ 1360 Book Now

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

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

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

From US$ 1093 Book Now

Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

The 3-bedroom Islamorada Modern Penthouse With Private Beach villa is situated approximately 5 minutes' walk from FNX Club by Islamorada Fitness and offers guests to relax with a Jacuzzi. Offering an… More

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

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

Offering an outdoor swimming pool, the 3-bedroom Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is situated merely 9 minutes' walk from Lobster Trap Art Gift… 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 Windley Key… 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 merely an 8… More

From US$ 394 Book Now

Pineapple Beach

130 Aregood Lane, Islamorada, United States Show map

Along with access to such natural sites as the 45 - acre Founders Park, approximately 25 minutes' walk away, the 5-bedroom Pineapple Beach Islamorada villa offers a swimming pool. The property… More

From US$ 2875 Book Now

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

135 Gulfview Drive, Islamorada, United States Show map

Situated approximately a 15-minute walk from Anne's Beach, Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9 Islamorada entices guests to explore various tourist… More

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

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

Located merely a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa features an outdoor… 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

Located just 1 km from Michelle Nicole Lowe Art Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has a heated pool and is ideal for… More

From US$ 587 Book Now