Special offers and Exclusive deals

Search Hotels

2026-08-01
2026-08-02
Guests

Filter Results

Hotels by class

Enter name

Price per night

Accommodation type

Attractions

Thematic hotels

Review rating

Hotel facilities

Room facilities

Apply Filters
Clear Filters

Holiday Homes in Islamorada

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

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

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

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

La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Staying at the 3-bedroom La Dolce Vita Villa Islamorada, guests can easily reach the Lobster Trap Art Gift Shop and Gallery, located approximately 6 km away. This Islamorada holiday home is suitable… More

From US$ 333 Book Now

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 offers a hot tub, ensuring a more relaxing stay. This 2-bedroom villa features opportunities… More

Book Now

Heart Of Morada

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

At the 3-bedroom Heart Of Morada Villa Islamorada, guests can enjoy canoeing and cycling as well as a location nearly 5 minutes' walk from the Hurricane Monument. More

Book Now

Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

Located just around the corner from the Lower Matecumbe Key, the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa offers opportunities for snorkelling in the area. More

From US$ 1956 Book Now

Casa Mar

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

Casa Mar Villa Islamorada enjoys a convenient location, 4 km from the Craig Key, and offers guests to unwind in a hot tub. The 3-bedroom holiday home features a heated pool and is ideal for up to 6… More

From US$ 657 Book Now

Antigua Place

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

Staying at the 3-bedroom Antigua Place Islamorada villa, guests can visit Anne's Beach, which is only 1.8 km away. Offering windsurfing, snorkelling, and fishing, the Islamorada holiday home is… More

Book Now

Beacon Reef 406

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

Featuring a Jacuzzi, the 2-bedroom Beacon Reef 406 Villa Islamorada is located about 5 minutes' walk from the History of Diving Museum and can host up to 4 guests. Providing guests with Wi-Fi and… More

Book Now

Paradise Palms Islamorada

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

During the stay at Paradise Palms Islamorada villa, guests can indulge in snorkelling, canoeing, and ping pong or visit the Michelle Nicole Lowe Art Gallery, located 4.5 km away. Located within a 10… More

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

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 the Lignumvitae Key Botanical State Park. The 2-bedroom villa features opportunities for… More

Book Now

Lyons Landing

105 Severino Drive, Islamorada, United States Show map

The 4-bedroom Lyons Landing Villa Islamorada is located approximately 20 minutes' walk from the Rain Barrel Village and welcomes its guests to enjoy windsurfing, snorkelling, and diving. More

Book Now

Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

At the 4-bedroom Martin Family Fish Camp Villa Islamorada, guests can enjoy windsurfing, snorkelling, and canoeing as well as a location about 5 minutes' walk from the Lobster Trap Art Gift Shop and… More

From US$ 823 Book Now

Palms 417

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

The 1-bedroom Palms 417 Villa Islamorada is located about 20 minutes' walk from the Indian Key State Historic Site and provides windsurfing, snorkelling, and diving for active guests. Offering a hot… More

Book Now

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 hot tub or visit the Indian Key State Historic Site, located about 20 minutes' walk away. This 1-bathroom villa… More

Book Now

Beacon Reef 503

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

During the stay at Beacon Reef 503 Villa Islamorada, guests can indulge in a hot tub or visit the class museum "Florida Keys History and Discovery Center", located an 18-minute walk away. The 2… More

Book Now

Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

Situated right around the corner from the Lower Matecumbe Key, the 2-bedroom Villa Riolo Islamorada is ideal for up to 6 guests. More

Book Now

Sandglass 4

74980 Overseas Hwy 4, Islamorada, United States Show map

Situated about 15 minutes' walk from the Lower Matecumbe Key, the 5-bedroom Sandglass 4 Islamorada villa provides access to numerous tourist attractions in the area. Suitable for up to 12 guests, the… More

From US$ 696 Book Now

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada hosts up to 12 guests and provides proximity to the Lower Matecumbe Key, situated only a 5-minute stroll away. Guests can… More

From US$ 1939 Book Now

Fl Keys Venetian Shores Waterfront With Ocean Access, Pool

141 Stromboli Drive, Islamorada, United States Show map

Located approximately 25 minutes' walk from the 45-acre Founders Park, Fl Keys Venetian Shores Waterfront With Ocean Access, Pool Islamorada villa has a swimming pool and is ideal for up to 8 guests.… More

From US$ 1011 Book Now

Palms 309

79901 Overseas Hwy., Islamorada, United States Show map

Palms 309 Villa Islamorada enjoys a beachfront location, a 10-minute drive from the Lobster Trap Art Gift Shop and Gallery, and offers guests to unwind in a hot tub. Guests can enjoy snorkelling… More

Book Now

Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Accommodating up to 3 guests, the 1-bedroom Sunshine Place Islamorada villa is situated 3.8 km from renowned cultural sites such as the Rain Barrel Sculpture Gallery. The property features… More

From US$ 384 Book Now

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 is suitable for 4 guests and provides a Jacuzzi for a truly relaxing stay. Guests can… More

Book Now

Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

82236 Overseas Highway, Islamorada, United States Show map

During the stay at Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa, guests can indulge in fishing or visit the Indian Key State Historic Site, located 25 minutes' walk away. Located 2.2 km… More

From US$ 1005 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Hosting up to 9 guests, Bella Villa Islamorada is nestled in a business area, about 15 minutes' walk from the Windley Key Fossil Reef Geological State Park. Guests can enjoy bowling and pool at the… More

Book Now

Waterfront Ocean Access Canal Kamp Key Homes

76412 Overseas Highway, Islamorada, United States Show map

Waterfront Ocean Access Canal Kamp Key Homes Islamorada is nestled just around the corner from the Lower Matecumbe Key and can accommodate up to 6 guests. Guests can enjoy snorkelling at the 3… More

From US$ 450 Book Now

Palms 407

79901 Overseas Hwy Unit 407, Islamorada, United States Show map

Situated within 6 km of the History of Diving Museum, the 2-bedroom Palms 407 Villa Islamorada boasts a Jacuzzi, as well as a spa salon for guests to relax in. At this Islamorada holiday home… More

Book Now

Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

Featuring an indoor water park and a wellness centre, the 6-bedroom Little Bay Compound Villa Islamorada offers guests to enjoy a beachfront location only 10 minutes' walk from the Keys History &… More

Book Now

West Plaza Del Lago

63 W Plaza Del Lago, Islamorada, United States Show map

During the stay at West Plaza Del Lago Islamorada villa, guests can indulge in windsurfing, snorkelling, and diving or visit the Lower Matecumbe Key, located a 25-minute walk away. More

Book Now

Beacon Reef 222

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

Situated 300 m from the History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada is ideal for up to 4 guests. This 2-bathroom villa features opportunities for snorkelling in the area,… More

Book Now

The Oasis

82703 Old Highway, Islamorada, United States Show map

Hosting up to 8 guests, The Oasis Villa Islamorada is nestled in a beach area, only 1.7 km from Anne s Beach. Guests can enjoy snorkelling, canoeing, and cycling at this 3-bedroom villa, located 10… More

From US$ 1964 Book Now

Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida

10610 San Remo Dr, Islamorada, United States Show map

The 3-bedroom Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida is located about a 20-minute stroll from the 45-acre Founders Park and allows guests to enjoy diving… More

Book Now

Beacon Reef 306

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

Located around 300 metres from the History of Diving Museum, the 2-bedroom Beacon Reef 306 Villa Islamorada is suitable for 4 guests and offers a Jacuzzi to relax in. Offering Wi-Fi, this Islamorada… More

Book Now

Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Featuring a hot tub, the 4-bedroom Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is located merely 7 minutes' walk from the Hurricane Monument and can host up to 7 guests. Providing… More

Book Now

Palms 301

79901 Overseas Hwy Unit 301, Islamorada, United States Show map

During the stay at the 2-bedroom Palms 301 Villa Islamorada, guests can indulge in a Jacuzzi or visit the Lignumvitae Key Botanical State Park, located about 20 minutes' walk away. This 2-bathroom… More

Book Now

Beacon Reef 310

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

Offering guests to unwind in a Jacuzzi, Beacon Reef 310 Villa Islamorada is located 25 minutes' walk from the Upper Matecumbe Key. Guests can enjoy windsurfing, snorkelling, and canoeing at the 2… More

Book Now

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

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

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa accommodates up to 6 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located merely an 8… More

From US$ 1403 Book Now