Islamorada, FL unique stayscozycozy

The widest selection of unusual accommodations in Islamorada, FL

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

35 Unique places to stay in Islamorada, FL

Houseboat Offers A Rooftop Deck For Stunning Views Of The Sunrise And Sunset. - Islamorada, FL
9.4 409 reviews
Islamorada, FL
2 4
£439/nighttotal: £878 (2 )

Houseboat Offers A Rooftop Deck For Stunning Views Of The Sunrise And Sunset.

houseboat - Tavernier
This houseboat resort is situated on the waterfront in Tavernier, within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, and within 3 miles of Florida Keys Dive Center and Harry Harris Park. The resort has received excellent ratings for its location, cleanliness and overall experience.
The houseboat offers a rooftop deck for stunning views of the sunrise and sunset, with a spacious 84 square metre layout and four bedrooms. Guests can enjoy a range of amenities, including a swimming pool, restaurant, bar, and free Wi-Fi in public areas, making it the perfect base for exploring the area.
360 Degree Waterview Houseboat - Islamorada, FL
9.9 388 reviews
Islamorada, FL
2 1
£174/nighttotal: £348 (2 )

360 Degree Waterview Houseboat

boat - Islamorada, Village of Islands
This solar and wind-powered houseboat is located in Islamorada, half a mile from the shore and a short distance from restaurants, bars, and music venues. The houseboat has received excellent ratings for location, cleanliness, and user experience.
The houseboat offers one bedroom and one bathroom, sleeping up to two guests. You can enjoy a fully equipped kitchen, a bathroom with a compost toilet and shower, a queen-sized bed, and a roof deck for enjoying cocktails. The houseboat also comes with a 12-foot skiff, a kayak, a stand-up paddleboard, and snorkeling gear, encouraging guests to explore the surrounding waters.
Waterfront Sunset View Aqua Villa At Sea Biscuit @ Mangrove Resort Llc - Islamorada, FL
9.5 52 reviews
Islamorada, FL
2 2
£323/nighttotal: £646 (2 )

Waterfront Sunset View Aqua Villa At Sea Biscuit @ Mangrove Resort Llc

house - Tavernier
This waterfront houseboat resort in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, offering easy access to both relaxation and healthcare. The resort boasts excellent user ratings and very good scores for location and cleanliness, ensuring a pleasant stay.
The 46 square metre houseboat features a comfortable layout with one bathroom, perfect for a couple or small family. Guests can enjoy a range of amenities, including a swimming pool, barbecue grills, and a tranquil garden, making it ideal for a relaxing getaway.
Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures - Islamorada, FL
9.8 493 reviews
Islamorada, FL
2 1
£333/nighttotal: £666 (2 )

Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures

houseboat - Islamorada, Village of Islands
This houseboat is located at Mile Marker 90, just south of Key Largo, offering easy access to the ocean and the bay via Tavernier Creek. The property has received excellent ratings from previous guests for its location, cleanliness and overall experience.
The houseboat spans 111 square metres and can accommodate up to four guests. It boasts a fully equipped kitchen, a terrace, a garden, a spa, a fitness centre, and parking, as well as access to a range of activities and services at the marina.
Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc - Islamorada, FL
9.3 42 reviews
Islamorada, FL
2 2
£330/nighttotal: £660 (2 )

Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc

house - Tavernier
The Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc is situated in Tavernier, a short walk from Baker's Cay Resort Beach and Mariners Hospital, and within a 5km radius of Florida Keys Dive Center and Harry Harris Park. This resort is highly rated for its location, cleanliness, and overall experience, making it an ideal choice for travellers seeking a relaxing and enjoyable stay.
The houseboat offers 46 square metres of space, featuring a bedroom, bathroom, and a terrace with stunning ocean views. Guests can enjoy the on-site swimming pool, spa, garden, and free WiFi in public areas, as well as explore the surrounding area with its beautiful beaches, parks, and dive centres.
Houseboat 2bd, 1 Bath Private Keys Cottage Mullet - Islamorada, FL
9.7 416 reviews
Islamorada, FL
2 2
£195/nighttotal: £390 (2 )

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet

boat - Islamorada, Village of Islands
This boat rental is located in Islamorada, Village of Islands, a short distance from the famous fishing spots and the mesmerizing sunsets of the Florida Keys. It has received excellent ratings for its cleanliness, location, and user experience.
The accommodation has two bedrooms and one bathroom, offering a comfortable and relaxing stay for couples or small families. Guests can enjoy access to a kitchen with a fridge and microwave, air conditioning, a garden, parking, and internet, as well as the option of renting a private boat to explore the surrounding waters.
The Salty Suite Islamorada House Boat - Islamorada, FL
10 3 reviews
Islamorada, FL
2 1
£149/nighttotal: £298 (2 )

The Salty Suite Islamorada House Boat

barge - Islamorada, Village of Islands
The Salty Suite, a unique floating accommodation, is moored in a protected, shallow basin (1.2-2.4 metres deep) behind the World Wide Sportsman in Islamorada, Village of Islands, with land-based amenities and restaurants less than 400 metres away.
This one-bedroom, one-bathroom houseboat accommodates up to three guests, offering solar-powered amenities, air conditioning, a kayak, a paddleboard, and a $50 discount for excursions with Key King Charters.
1.5 Bedroom, 1 Bath With Back Deck. Pet Friendly With 2 Queen And 2 Twin Beds. - Islamorada, FL
9.6 4 reviews
Islamorada, FL
2 2
£354/nighttotal: £708 (2 )

1.5 Bedroom, 1 Bath With Back Deck. Pet Friendly With 2 Queen And 2 Twin Beds.

houseboat - Tavernier
This Tavernier houseboat, situated 0.8km from Mariners Hospital and within 4.8km of both the Florida Keys Dive Center and Harry Harris Park, offers a tranquil waterfront escape.
Sleeping up to four guests in two bedrooms and one bathroom, this self-catering vessel boasts air conditioning, Wi-Fi, and pet-friendly accommodation, with potential for fishing, kayaking, or paddleboarding directly from the boat.
Florida Keys Boat Trips Multi Activity - Islamorada, FL
Islamorada, FL
2 1
£292/nighttotal: £584 (2 )

Florida Keys Boat Trips Multi Activity

boat - Islamorada, Village of Islands
This Islamorada boat rental, located a short walk from Windley Key and 0.8km from Windley Key Fossil Reef Geological State Park, offers easy access to local attractions.
Sleeping up to 11 guests in one bedroom and one bathroom, this vessel boasts private beach access, proximity to Theater of the Sea (2.3km), and allows pets.
Billfish: 1-bedroom House Boat In Perfect Islamorada With Ac - Islamorada, FL
Islamorada, FL
2 1
£328/nighttotal: £656 (2 )

Billfish: 1-bedroom House Boat In Perfect Islamorada With Ac

houseboat - Islamorada, Village of Islands
This unique floating accommodation, a houseboat, is situated in the Matecumbe neighbourhood of Islamorada, Village of Islands, placing guests within 1.5 kilometres of the Keys History & Discovery Centre and History of Diving Museum, and a short distance from Bud n' Mary's Dive Center and Florida Keys Brewing Co.
This dwelling offers air conditioning, internet, one bedroom with a full bed, a living room with a futon, and one bathroom, accommodating up to two guests with an 11:00 AM check-out time.
1 Bd Private Houseboat/ Cottage Tarpon - Islamorada, FL
9.4 617 reviews
Islamorada, FL
2 2
£157/nighttotal: £314 (2 )

1 Bd Private Houseboat/ Cottage Tarpon

apartment - Islamorada, Village of Islands
This boat is situated in Islamorada, close to the village centre and within easy reach of the famous bridges and fishing spots. It boasts excellent ratings for location, cleanliness, and overall user experience.
The accommodation comes with two bedrooms and one bathroom, offering comfortable living space for a small group. Amenities include air conditioning, a kitchen, a garden, and parking, ensuring a pleasant and convenient stay.
Aqua Lodge Houseboat "Captain's Quarters" - Islamorada, FL
9.6 15 reviews
Islamorada, FL
2 2
£410/nighttotal: £820 (2 )

Aqua Lodge Houseboat "Captain's Quarters"

houseboat - Tavernier
This houseboat is situated in Tavernier, a short walk from Baker's Cay Resort Beach and Mariners Hospital, with the Florida Keys Dive Center and Harry Harris Park within easy reach. The property has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The two-bedroom, one-bathroom houseboat can accommodate up to four guests, offering a spacious and relaxing environment. Guests can enjoy a range of amenities, including a kitchen, air conditioning, a swimming pool, and internet access, as well as the added benefit of a waterfront location and pet-friendly policies.

Check Out Family-Friendly Unusual Places to Stay in Islamorada, FL

Keep the whole group happy with exceptional beach access at our family-friendly unique stays in Islamorada, FL.

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.6 85 reviews
Islamorada, FL
2 2
£361/nighttotal: £722 (2 )

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada

apartment - Islamorada, Village of Islands
This charming cottage is situated in Islamorada, just a short distance from the Village of Islands' centre, offering easy access to fishing piers and the lively downtown area. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for a relaxing getaway.
The cottage comfortably sleeps four guests in two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private backyard, a community pool, a fully equipped kitchen, a washer and dryer, a private porch, and bikes for exploring the area.
Charming House Boat With 2 Bedrooms And Wifi, Ac In Wonderful Islamorada - Islamorada, FL
10 5 reviews
Islamorada, FL
2 2
£471/nighttotal: £942 (2 )

Charming House Boat With 2 Bedrooms And Wifi, Ac In Wonderful Islamorada

houseboat - Islamorada, Village of Islands
This Islamorada houseboat, situated in the Matecumbe district, offers easy walking access to the Florida Keys Brewing Co. and the Hurricane Monument.
The two-bedroom, one-bathroom floating home sleeps four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, and a barbecue; nearby attractions include Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park.
Bungalow #4 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.7 97 reviews
Islamorada, FL
2 2
£352/nighttotal: £704 (2 )

Bungalow #4 - 2 Bed/1 Bath & Pool In Islamorada

apartment - Islamorada, Village of Islands
This charming bungalow is situated just a short distance from the lively downtown area of Islamorada, offering easy access to the renowned fishing piers and the scenic Overseas Highway. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cottage comfortably accommodates up to four guests across two bedrooms and one bathroom, spanning 88 square metres. Guests can enjoy a private backyard and porch, a community heated pool, a fully equipped kitchen with modern appliances, a washer and dryer, complimentary bicycles, and a security camera for added peace of mind.
Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp - Islamorada, FL
10 181 reviews
Islamorada, FL
2 2
£527/nighttotal: £1054 (2 )

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp

apartment - Islamorada, Village of Islands
This family-friendly holiday home is located in Islamorada, just a short drive from the San Pedro Underwater Archaeological Preserve State Park, Robbie’s of Islamorada, and Indian Key Historic State Park, all within a 3 km radius. This property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom dwelling can comfortably accommodate up to five guests. The property offers a range of amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and concierge services, as well as a tennis court and free parking.

Best Islamorada, FL unusual places with a garden

Aqua Lodge Houseboat "Tarpon" - Islamorada, FL
9.8 34 reviews
Islamorada, FL
2 1
£346/nighttotal: £692 (2 )

Aqua Lodge Houseboat "Tarpon"

houseboat - Tavernier
This houseboat is located on the waterfront in Tavernier, just a 15-minute walk from Baker's Cay Resort Beach and Mariners Hospital and within 3 miles of the Florida Keys Dive Center and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and user experience.
The houseboat features one bedroom and one bathroom, making it ideal for a couple or small family. Amenities include a kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace, a garden, parking, and internet access. Guests can also enjoy the unique experience of living on the water, with direct access to the beautiful Florida Keys scenery and potential water activities.
Island Sanctuary Islamorada - Islamorada, FL
9.4 25 reviews
Islamorada, FL
2 2
£277/nighttotal: £554 (2 )

Island Sanctuary Islamorada

houseboat - Tavernier
This luxury houseboat in Tavernier, Florida Keys, boasts a prime waterfront location, situated within 3.2km of Mariners Hospital and under 9.7km from Islamorada County Park.
The 93 square metre vessel offers two bedrooms, one bathroom, sleeping up to two guests, and features a kitchen with a fridge, air conditioning, a swimming pool, terrace, garden, and spa, plus on-site parking and housekeeping services available upon request.
Perfect Escape To The Ocean - Islamorada, FL
9.6 64 reviews
Islamorada, FL
2 2
£428/nighttotal: £856 (2 )

Perfect Escape To The Ocean

barge - Islamorada, Village of Islands
This solar-powered barge, offering unique floating accommodation in Islamorada, Village of Islands, is situated in the Florida Keys, its precise location within the archipelago to be confirmed upon booking.
The vessel boasts two bedrooms, one bathroom, sleeping up to four guests, and includes a kitchen, air conditioning, and internet access; enjoy swimming in the Florida Keys waters and exploring nearby attractions.
Aqua Lodge Houseboat "Sea Turtle" - Islamorada, FL
9.3 44 reviews
Islamorada, FL
2 1
£323/nighttotal: £646 (2 )

Aqua Lodge Houseboat "Sea Turtle"

houseboat - Tavernier
This houseboat is situated in Tavernier, a short walk from Baker's Cay Resort Beach and Mariners Hospital, offering a peaceful escape from the hustle and bustle of everyday life. The property has excellent user, location, and cleanliness ratings, indicating a high-quality experience. This floating home features one bedroom and one bathroom, accommodating up to two guests. Amenities include a private pool, a terrace, and a garden, as well as internet access, air conditioning, and a kitchen with a fridge and microwave.

Frequently asked questions about unique stays in Islamorada, FL

  • What attractions are Islamorada, FL and the nearby cities famous for?

    Islamorada is known for its beautiful beaches, fishing, and boating. You can find plenty of shops and restaurants along the Overseas Highway, and there are a number of great places to go kayaking, paddleboarding, and snorkeling. The area is also home to the History of Diving Museum, which is a great place to learn about the history of diving in the Florida Keys. If you're looking for something a little more adventurous, you can take a day trip to Key West, which is about 100 miles south of Islamorada. Key West is known for its vibrant nightlife, quirky shops, and historical sites.
  • What clothing or gear is recommended for the climate in Islamorada, FL?

    You'll definitely want to pack light, breathable clothing, as the weather in Islamorada is typically hot and humid. You'll also want to bring sunscreen, a hat, and sunglasses to protect yourself from the sun. If you plan on spending time on the water, you'll want to bring swimwear, water shoes, and a rash guard to protect your skin from the sun and the elements.
  • Is there Wi-Fi or good mobile phone coverage in and around Islamorada, FL?

    You'll find Wi-Fi available at most hotels, restaurants, and cafes in Islamorada. Mobile phone coverage is generally good, but there may be some areas where reception is spotty. If you're planning on spending a lot of time outdoors, you might want to consider bringing a portable Wi-Fi hotspot.
  • What other cities should you visit around Islamorada, FL?

    If you're looking for a more laid-back vibe, you can visit Marathon, which is located about 30 miles south of Islamorada. Marathon is known for its beautiful beaches, fishing, and boating. If you're looking for a more bustling atmosphere, you can visit Key West, which is about 100 miles south of Islamorada. Key West is known for its vibrant nightlife, quirky shops, and historical sites.
  • What should you know about unique stays in Islamorada, FL before booking?

    Islamorada has a number of unique accommodations, including waterfront homes, villas, and even a few bed and breakfasts. If you're looking for a truly unique experience, you can stay in a 'floating' hotel room at the Cheeca Lodge and Resort. The Cheeca Lodge is a historic resort that has been welcoming guests for over 60 years. It is located on a beautiful stretch of beach and offers a variety of amenities, including a spa, a restaurant, and a marina. The resort also has a number of unique accommodations, including a few floating hotel rooms that are located over the water. These rooms offer stunning views of the ocean and are a great way to experience Islamorada in a truly unique way.

Popular destinations

Explore Unique Stays with a Hot Tub in Islamorada, FL

Every premier waterfront unique stay in Islamorada, FL comes equipped with its own private hot tub.

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp - Islamorada, FL
10 181 reviews
Islamorada, FL
2 2
£527/nighttotal: £1054 (2 )

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp

apartment - Islamorada, Village of Islands
This family-friendly holiday home is located in Islamorada, just a short drive from the San Pedro Underwater Archaeological Preserve State Park, Robbie’s of Islamorada, and Indian Key Historic State Park, all within a 3 km radius. This property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom dwelling can comfortably accommodate up to five guests. The property offers a range of amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and concierge services, as well as a tennis court and free parking.

Best pet friendly Islamorada, FL unique stays

Among the 35 accommodations in Islamorada, FL, here are the 2 best pet friendly unique accommodations

Off-grid Islamorada Houseboat - Islamorada, FL
10 9 reviews
Islamorada, FL
2 2
£435/nighttotal: £870 (2 )

Off-grid Islamorada Houseboat

barge - Islamorada, Village of Islands
This secluded houseboat in Islamorada, Village of Islands, offers complete privacy and unparalleled access to the Florida Keys' marine ecosystem, its precise location within the vast waterways determining proximity to specific landmarks.
The two-bedroom, one-bathroom floating accommodation sleeps four guests and features a kitchen, air conditioning, internet access, and provides a unique off-grid experience with opportunities for fishing and watersports.
Florida Keys Boat Charters - Islamorada, FL
Islamorada, FL
6 1
£345/nighttotal: £1035 (3 )

Florida Keys Boat Charters

boat - Islamorada, Village of Islands
This Islamorada boat charter is centrally located, within a 1.4 km walk of Windley Key Fossil Reef Geological State Park and a few kilometres of the Theatre of the Sea and History of Diving Museum.
Sleeping up to 11 guests in one bedroom and one bathroom, this vessel offers sea views and pet-friendly accommodation, ideally positioned for exploring Islamorada's attractions including Pigeon Key (15 km) and John Pennekamp Coral Reef State Park (27-34 km).

Discover 5-Star Unusual Places to Stay in Islamorada, FL

Hand-picked for quality, these luxury unique stays in Islamorada, FL blend coastal character with 5-star comfort.

1.5 Bedroom, 1 Bath With Back Deck. Pet Friendly With 2 Queen And 2 Twin Beds. - Islamorada, FL
9.6 4 reviews
Islamorada, FL
2 2
£354/nighttotal: £708 (2 )

1.5 Bedroom, 1 Bath With Back Deck. Pet Friendly With 2 Queen And 2 Twin Beds.

houseboat - Tavernier

Best Unique Stays with a Pool in Islamorada, FL

Enjoy the luxury of an on-site pool during your coastal escape at these unique stays in Islamorada, FL.

Aqua Lodge Houseboat "Yellow Tail " - Islamorada, FL
9.6 80 reviews
Islamorada, FL
2 1
£354/nighttotal: £708 (2 )

Aqua Lodge Houseboat "Yellow Tail "

houseboat - Tavernier
Aqua Lodge Houseboat "The Grey Lady" - Islamorada, FL
9.7 78 reviews
Islamorada, FL
6 4
£532/nighttotal: £1596 (3 )

Aqua Lodge Houseboat "The Grey Lady"

houseboat - Tavernier
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 74 reviews
Islamorada, FL
2 3
£443/nighttotal: £886 (2 )

Aqua Lodge Houseboat "Calypso"

houseboat - Tavernier
©2026 cozycozy.com