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2026-10-30
2026-10-31
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Beachfront hotels 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

Sands Of Islamorada

80051 Overseas Highway, Islamorada, United States Show map

Located about 10 minutes by car from Lobster Trap Art Gift Shop and Gallery, Sands Of Islamorada hotel offers air-conditioned rooms 3.4 km from the class museum "Florida Keys History and Discovery… More

From US$ 200 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

Coconut Cove Resort & Marina

84801 Overseas Highway, Islamorada, United States Show map

Featuring a picnic area and barbecue grills, the 2-star Coconut Cove Resort & Marina Islamorada is situated just a 5-minute walk from Windley Key Island. 4.9 km from Hurricane Monument, the inn… More

From US$ 245 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

La Jolla Resort

82216 Overseas Highway, Islamorada, United States Show map

La Jolla Resort Islamorada, located a 14-minute walk from History of Diving Museum, features Wi-Fi in public areas. This resort lies in proximity to the world-class museum "Florida Keys History and… More

From US$ 181 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

Anglers Reef Paradise

110 Anglers Way 110, Islamorada, United States Show map

Situated approximately a 5-minute walk from 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

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

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

Beacon Reef 501

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

Featuring a fitness room for active guests, Beacon Reef 501 Villa Islamorada is just a 5-minute walk from History of Diving Museum. Located fairly close to Island Community Church, this 2-bedroom… More

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The Lighthouse- Ocean Views, Game Room, Pool ,Dock Access

84745 Old Hwy #8, Islamorada, United States Show map

The Lighthouse- Ocean Views, Game Room, Pool ,Dock Access Islamorada villa provides spa therapy and a terrace for a delightful experience, and is located 8 minutes' walk from Windley Key Fossil Reef… More

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Casa Mar

115 Ponce De Leon Blvd, Islamorada, United States Show map

Casa Mar Villa Islamorada enjoys a convenient location, 4 km from Craig Key Island, and offers guests to unwind in a hot tub. The 3-bedroom holiday home features a heated pool and is ideal for up to… More

From US$ 657 Book Now

Is55Flr Captain'S Cove

227 El Capitan Dr, Islamorada, United States Show map

Located a 15-minute walk from Anne's Beach, Is55Flr Captain'S Cove Islamorada villa offers fitness classes, as well as a fitness room for active guests. More

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Antigua Place

126 Ponce De Leon Blvd, Islamorada, United States Show map

The 3-bedroom Antigua Place Islamorada villa is located about 20 minutes on foot from Anne's Beach and allows guests to enjoy windsurfing, snorkelling, and fisheries. More

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Beacon Reef 406

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

Located around 5 minutes' walk from History of Diving Museum, the 2-bedroom Beacon Reef 406 Villa Islamorada offers a Jacuzzi for additional relaxation. Providing guests with Wi-Fi and parking, this… More

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Paradise Palms Islamorada

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

Located just an 8-minute walk from Windley Key Fossil Reef Geological State Park, the 3-bedroom Paradise Palms Islamorada villa is suitable for 8 guests and provides an outdoor swimming pool to relax… More

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Little Bay Cottage

82246 Overseas Hwy, Islamorada, United States Show map

Situated about 10 minutes' walk from Keys History & Discovery Center, the 2-bedroom Little Bay Cottage Islamorada entices guests with snorkelling, diving, and fisheries in the area. Providing guests… More

From US$ 549 Book Now

Palms 404

79901 Overseas Hwy Unit 404, Islamorada, United States Show map

Offering a Jacuzzi for a relaxing experience, Palms 404 Villa Islamorada is located a 20-minute walk from Lignumvitae Key Botanical State Park. The 2-bedroom villa features opportunities for… More

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Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

Situated around 5 minutes' walk from Lobster Trap Art Gift Shop and Gallery, the 4-bedroom Martin Family Fish Camp Villa Islamorada entices guests with windsurfing, snorkelling, and canyoning in the… More

From US$ 823 Book Now

Palms 417

79901 Overseas Highway #417, Islamorada, United States Show map

Featuring a heated pool, the 1-bedroom Palms 417 Villa Islamorada is suitable for up to 3 people and is located around 20 minutes' walk from Indian Key State Historic Site. Providing guests with Wi… More

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Palms 317

79901 Overseas Hwy Unit 317, Islamorada, United States Show map

During the stay at the 1-bedroom Palms 317 Villa Islamorada, guests can indulge in a Jacuzzi or visit Indian Key State Historic Site, located about 20 minutes' walk away. This 1-bathroom villa… More

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