Search special places in Islamorada, FL from 100+ sites!

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

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Islamorada, FL unique stays
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

35 Unique places to stay in Islamorada, FL

Our Favorite Family Unique Stays in Islamorada, FL

Family vacations in a unique stay in Islamorada, FL offer one-of-a-kind accommodation near the water.

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, located in the Matecumbe district, offers convenient walking distance to the Florida Keys Brewing Co. and the Hurricane Monument.
The two-bedroom, one-bathroom vessel sleeps four and features a fully equipped kitchen with a lobster pot, microwave, and outdoor barbecue, plus air conditioning and a smart TV.
Baycation Houseboat | Florida Keys Waterfront Stay - Islamorada, FL
9.8 490 reviews

Baycation Houseboat | Florida Keys Waterfront Stay

barge, Islamorada, Village of Islands
This houseboat is located at Mile Marker 90, at the northern edge of Islamorada, offering easy access to both the ocean and bay. The property has received excellent ratings for user experience, location, and cleanliness.
This floating home is 1190 square feet and comfortably accommodates up to four guests. The houseboat offers a fully equipped kitchen, a spacious living area, a triple upper deck, a pet-friendly environment, and a relaxing atmosphere.
Aqua Lodge Houseboat -"Conch Shell" - Islamorada, FL
9.3 42 reviews

Aqua Lodge Houseboat -"Conch Shell"

boat, Tavernier
The Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc is located in Tavernier, Florida, just a 15-minute walk from Baker's Cay Resort Beach and Mariners Hospital. This unique houseboat offers a memorable experience on the water with excellent ratings for location, cleanliness, and overall user satisfaction.
The 500-square-foot houseboat features one bathroom and a range of amenities including a swimming pool, spa, garden, terrace, and parking. Guests can enjoy free Wi-Fi in public areas, a smoke-free environment, and easy access to nearby attractions like the Florida Keys Dive Center and Harry Harris Park.
Islamorada Bungalow 3 - Islamorada, FL
9.6 84 reviews

Islamorada Bungalow 3

bungalow, Islamorada, Village of Islands
This cozy cottage is located in Islamorada, just a short distance from the center of the Village of Islands, offering easy access to the famous fishing spots and the breathtaking sunsets of the Florida Keys. It consistently receives excellent ratings for location, cleanliness, and user experience.
The bungalow features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy amenities like a private backyard, a community heated pool, a private porch, washer and dryer, bikes, and a security camera.

Best Islamorada, FL unique accommodations with a garden

Aqua Lodge Houseboat "Captain's Quarters" - Islamorada, FL
9.6 15 reviews

Aqua Lodge Houseboat "Captain's Quarters"

houseboat, Tavernier
This houseboat is located in Tavernier, Florida, just a short walk from Baker's Cay Resort Beach and Mariners Hospital, offering easy access to the area's attractions. Guests rave about the unique experience and excellent ratings.
The houseboat features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy amenities like a kitchen, air conditioning, a swimming pool, and internet access, ensuring a comfortable and enjoyable stay.
Houseboat 2bd, 1 Bath Private Keys Cottage Mullet - Islamorada, FL
9.7 413 reviews

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet

boat, Islamorada, Village of Islands
This boat is located in Islamorada, just a short drive from the Overseas Highway and close to the village's attractions. It has received excellent ratings for location, cleanliness, and user experience.
The boat has two bedrooms and one bathroom, making it ideal for a small family or group of friends. It comes equipped with a kitchen, air conditioning, and a garden, and offers a 20% discount on private boat rentals.
2/1 Floating Villa W/ Water View The Pelagic - Islamorada, FL
9.6 77 reviews

2/1 Floating Villa W/ Water View The Pelagic

barge, Islamorada, Village of Islands
This Islamorada barge rental, located in the Village of Islands, offers easy access to local attractions; precise distances to specific landmarks require further inquiry.
The two-bedroom, one-bathroom vessel sleeps six guests and features a full kitchen, Wi-Fi, air conditioning, and pet-friendly accommodations, perfect for exploring the Florida Keys' abundant marine life.
Aqua Lodge Houseboat "Tarpon" - Islamorada, FL
9.8 34 reviews

Aqua Lodge Houseboat "Tarpon"

boat, Tavernier
This houseboat in Tavernier is located within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, offering easy access to the area's attractions. The property has received excellent ratings for user experience, location, and cleanliness.
The boat features one bedroom and one bathroom, and comes equipped with a kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking. Enjoy the waterfront location, relax in the private pool, and take advantage of the nearby beach, dive center, and park.

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, world-class fishing, and the Florida Keys Overseas Highway, a scenic drive that connects the islands. Theater of the Sea is a popular attraction in Islamorada, where you can see dolphins, sea lions, and other marine animals. Just a short drive away in Key Largo is John Pennekamp Coral Reef State Park, a great place to snorkel or scuba dive.
  • What clothing or gear is recommended for the climate in Islamorada, FL?

    You'll want to pack light, breathable clothing for the hot and humid weather. Don't forget your swimsuit, sunscreen, and sunglasses. You'll also want to bring a hat and comfortable walking shoes for exploring the area. And if you plan on doing any water activities, be sure to pack water shoes or sandals to protect your feet from the coral.
  • Is there Wi-Fi or good mobile phone coverage in and around Islamorada, FL?

    Most hotels and restaurants in Islamorada offer Wi-Fi, and mobile phone coverage is generally good. However, there are some areas, especially out on the water or in remote parts of the Keys, where service may be spotty. It's always a good idea to have a backup plan, like a portable Wi-Fi hotspot, just in case.
  • What other cities should you visit around Islamorada, FL?

    If you're looking to explore more of the Florida Keys, Key Largo and Marathon are both worth a visit. Key Largo is home to the John Pennekamp Coral Reef State Park, and Marathon is known for its beautiful beaches and the Seven Mile Bridge. You can also take a day trip to Key West, the southernmost point in the United States.
  • What should you know about unique stays in Islamorada, FL before booking?

    Islamorada has a variety of unique accommodations, from waterfront hotels to cozy bed and breakfasts. If you're looking for something special, consider staying in a houseboat or a condo on the beach. Just be sure to book in advance, especially during peak season.

Popular destinations

Traveler-Approved Unusual Accommodations with Jacuzzi in Islamorada, FL

Reward yourself with an unforgettable private soak in a hot tub or jacuzzi at these unique Islamorada, FL stays.

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,sups - Islamorada, FL
10 178 reviews

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,sups

bungalow, Islamorada, Village of Islands
This house is situated by the sea in Islamorada, Village of Islands, within 2 miles of San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park. It has excellent user, location and cleanliness ratings.
The house is suitable for families and groups, with 2 bedrooms and a guest capacity of 5. It includes a cozy interior with a fireplace, a fully equipped kitchen with a refrigerator and an oven, and a balcony. Guests can also enjoy amenities such as a water park, outdoor pool, spa tub, concierge services, a garden, and barbecue grills.

Best pet friendly Islamorada, FL unique stays

Among the 35 accommodations in Islamorada, FL, here are the 3 best pet friendly unique accommodations

Florida Keys Boat Trips Multi Activity - Islamorada, FL
No reviews

Florida Keys Boat Trips Multi Activity

boat, Islamorada, Village of Islands
This Islamorada boat rental, sleeping up to 11 guests, is conveniently located near Windley Key (a 17-minute walk) and Windley Key Fossil Reef Geological State Park (0.5 miles), with Theater of the Sea just 1.4 miles away.
The one-bedroom, one-bathroom vessel offers private beach access with direct ocean views, pet-friendly accommodations, parking, and proximity to snorkeling opportunities.
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
This Tavernier houseboat, located 0.5 miles from Mariners Hospital and within 3 miles of the Florida Keys Dive Center, Harry Harris Park, and the Old Road Gallery, offers convenient access to local attractions.
This two-bedroom, one-bathroom vessel sleeps four guests and includes air conditioning, internet, and pet-friendly accommodations, perfect for exploring Tavernier's waterfront.
"Manatee" Houseboat With Rooftop Sunset View - Islamorada, FL
9.4 409 reviews

"Manatee" Houseboat With Rooftop Sunset View

boat, Tavernier
This houseboat resort is located in Tavernier, Florida, just a short walk from Baker's Cay Resort Beach and Mariners Hospital, and within a 3-mile drive of several other attractions. The property consistently receives excellent ratings from guests for its cleanliness, location, and overall experience.
The houseboat offers a unique waterfront experience with a spacious 900 square feet layout, featuring four bedrooms. Guests can enjoy amenities such as a rooftop terrace with stunning views, a swimming pool, a restaurant and bar, and free Wi-Fi in public areas.

Top-Rated Oceanfront Unique Stays in Islamorada, FL

Wake up to the turquoise waters of the Florida Keys! Discover one-of-a-kind oceanfront escapes near the world-famous Robbie’s of Islamorada, the History of Diving Museum, and the stunning reefs of Hen and Chickens.

Aqua Lodge Houseboat 2bd/1bth! - Islamorada, FL
9.6 114 reviews

Aqua Lodge Houseboat 2bd/1bth!

barge, Islamorada, Village of Islands

Best Unique Stays with a Pool in Islamorada, FL

Pool access at a unique stay in Islamorada, FL makes a swim the perfect complement to a day by the water.

Aqua Lodge Houseboat "Sea Turtle" - Islamorada, FL
9.3 44 reviews

Aqua Lodge Houseboat "Sea Turtle"

barge, Tavernier
Aqua Lodge Houseboat "The Grey Lady" - Islamorada, FL
9.8 75 reviews

Aqua Lodge Houseboat "The Grey Lady"

barge, Tavernier
©2026 cozycozy.com