The widest selection of unusual accommodations in Islamorada, FL

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

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Islamorada, FL unique stays
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35 Unique places to stay in Islamorada, FL

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

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

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

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

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

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

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

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

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

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

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
No reviews

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

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

Aqua Lodge Houseboat "Yellow Tail "

houseboat, Tavernier
Aqua Lodge Houseboat "The Grey Lady" - Islamorada, FL
9.7 78 reviews

Aqua Lodge Houseboat "The Grey Lady"

houseboat, Tavernier
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 74 reviews

Aqua Lodge Houseboat "Calypso"

houseboat, Tavernier
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