
House holiday rentals in Islamorada
Find and book unique houses on Airbnb
Top-rated house rentals in Islamorada
Guests agree: These houses are highly rated for location, cleanliness and more.

Waterfront Sunsets, Great Price, Relaxing Spot!!!
Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Flakey's
Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

Oceanfront Tiny Villa in the Heart of the FL Keys
Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Great key Largo home with water front and pool
we have a dog clean fee , always ask the before booking Fantastic canal front home located in Key Largo. Bring your own boat and enjoy it all! The home is minutes away from Gilbert resort, best seafood in the world at any number of local restaurants, Souvenir stores and the best fishing and diving spots. The home has 2 bedrooms and 2 bathrooms, fully furnished, spacious living room with large TV, Full kitchen with all appliances and amenities and a beautiful deck

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Spacious 3Br/3Ba, 70ft Dock, March avail VACA23-16
Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)
Popular amenities for Islamorada house rentals
House rentals with a pool

Pristine pool front home w/ocean views Anglers 148

Beach House in Marathon with Amazing Backyard!

Blue House Marine in Key Largo

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Oceanfront mermaid house pool and dock

Waterfront Key Largo Home - Tropical Paradise

Lagoona-Matata

Mariners 212 Great Location with Marina Views
Weekly house rentals

Villa 7218 on Duck key - Boat Slip Available

Flamingo Palms-April availability

Waterfront 2-bedroom Home w/Pool and Spa

Waterfront Private Home w/Pool-Family&Pet Friendly

Grand Sands /120'Dock/Mini Golf/HtdPool /Game Room

Viamarhe House-Private beach, Kayak, yard games

Oceanview Escape

Oceanview Marathon - Screened Porch, Theater & Bar
Private house rentals

Waterfront with Boat Lift/Kayaks and Hot Tub

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

Florida Keys Oceanside Utopia

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

3/2 Home w Dock, lagoon, kayaks!

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Boating Paradise Villa rental Lic# VACA-25-124

P01 - New 3 bed, 3 bath with private pool
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $793 NZD | $793 NZD | $784 NZD | $771 NZD | $814 NZD | $850 NZD | $805 NZD | $754 NZD | $728 NZD | $728 NZD | $769 NZD | $784 NZD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about house rentals in Islamorada

Total holiday rentals
Explore 270 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $137 NZD per night before taxes and fees

Verified guest reviews
Over 1,930 verified reviews to help you choose

Family-friendly holiday rentals
260 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Holiday rentals with a pool
170 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
270 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.9 Average rating
Islamorada stays are highly rated by guests—averaging 4.9 out of 5!
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Coral Castle
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Calusa Campground
- Seven Mile Bridge
- The Turtle Hospital
- Robbies Marina Of Islamorada
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Homestead Bayfront Park
- Founder's Park
- Ernest F. Coe Visitor Center
- History Of Diving Museum
- Harry Harris Beach and Park
- Fruit & Spice Park





