
House vacation 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.

Off The Charts-Waterfront Tiki Bar & Private Dock
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets. For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.

Islamorada Bungalow # 5
Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

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.

The Paradise 2
Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!

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

Heart of Islamorada ~ Private Boat Dockage

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

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

Keys to Ohana. Ocean views. Private Pool, Hot Tub

3/2 Home w Dock, lagoon, kayaks!

P01 - New 3 bed, 3 bath with private pool

Marathon one-level home on the Marina - with slip!
Weekly house rentals

Florida Keys Oceanside Utopia

KCB Tropical Escape

Oceanfront mermaid house pool and dock

Viamarhe House-Private beach, Kayak, yard games

Oceanview Escape

*NEW* Casa Coco-Pool/Tennis/Ramp

Gorgeous Ocean View Home!

Golf Coast Oasis near Sombrero Beach
Private house rentals

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

Flamingo Palms-JUNE Dates available at a discount!

Oceanfront with Pool near Sombrero Beach

Boating Paradise Villa rental Lic# VACA-25-124

Casa Blue Flamingo

Waterfront Home| Heated Pool + Dock+Kayaks

Oceanview Marathon - Screened Porch, Theater & Bar

Villa Bella 3/3 with Private Pool & Dock!
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$96,860 GYD | G$96,860 GYD | G$95,814 GYD | G$94,140 GYD | G$99,371 GYD | G$103,764 GYD | G$98,324 GYD | G$92,048 GYD | G$88,910 GYD | G$88,910 GYD | G$93,931 GYD | G$95,814 GYD |
| 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 vacation rentals
Explore 270 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at G$16,736 GYD per night before taxes and fees

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

Family-friendly vacation rentals
260 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 130 rentals that welcome pets

Vacation rentals with a pool
170 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
270 of Islamorada vacation 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Beachfront rentals Islamorada
- Fitness-friendly rentals Islamorada
- Rentals with pools Islamorada
- Family-friendly rentals Islamorada
- Resort rentals Islamorada
- Beach condo rentals Islamorada
- Hotel rooms Islamorada
- Townhouse rentals Islamorada
- Bungalow rentals Islamorada
- Rentals with an EV charger Islamorada
- Rentals with breakfast Islamorada
- Pet-friendly rentals Islamorada
- Rentals with a fireplace Islamorada
- Rentals with a patio Islamorada
- Rentals with beach access Islamorada
- Serviced apartment rentals Islamorada
- Waterfront rentals Islamorada
- Apartment rentals Islamorada
- Rentals with a washer and dryer Islamorada
- Rentals with a fire pit Islamorada
- Rentals with a hot tub Islamorada
- Condo rentals Islamorada
- Rentals with outdoor seating Islamorada
- Luxury rentals Islamorada
- Beach house rentals Islamorada
- Villa rentals Islamorada
- Rentals with a kayak Islamorada
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- 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
- The Turtle Hospital
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- 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





