
House vacation rentals in Islamorada
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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.

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

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!!

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!

Your Keys Getaway!
Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.
Popular amenities for Islamorada house rentals
House rentals with a pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Heart of Islamorada ~ Private Boat Dockage

Pristine pool front home w/ocean views Anglers 148

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

3/2 Home w Dock, lagoon, kayaks!

4BR 3B, Heated Pool & Spa, 60' Dock

Waterfront Home 37.5-ft dock, Cabana Club Included

Casa Solaris | Key Largo home with Private Pool!
Weekly house rentals

KCB Tropical Escape

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

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Viamarhe House-Private beach, Kayak, yard games

Waterfront / Ocean Access Canal / Kamp Key

Boat Dock+King Bed & Cabana Club
Private house rentals

Florida Keys Oceanside Utopia

Waterfront with Boat Lift/Kayaks and Hot Tub

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

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

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

Oceanfront mermaid house pool and dock

Oceanfront with Pool near Sombrero Beach

Oceanview Escape
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$96,670 GYD | G$96,670 GYD | G$95,627 GYD | G$93,956 GYD | G$99,176 GYD | G$103,561 GYD | G$98,132 GYD | G$91,868 GYD | G$88,736 GYD | G$88,736 GYD | G$93,747 GYD | G$95,627 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$16,703 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!
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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
- Everglades Alligator Farm
- Bahia Honda State Park
- Theater of the Sea
- Seven Mile Bridge
- Calusa Campground
- Robbies Marina Of Islamorada
- Monkey Jungle
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Ernest F. Coe Visitor Center
- Dolphin Research Center
- Founder's Park
- Homestead Bayfront Park
- History Of Diving Museum
- Harry Harris Beach and Park
- Fruit & Spice Park





