
House holiday rentals in Islamorada
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Top-rated house rentals in Islamorada
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*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes
Perfectly situated in KCB w/ 37.5' of dockage on a wide and pristine canal that leads easy access to both the Ocean & the Gulf, our newly listed 1/2 duplex is newly renovated w/ brand new AC, appliances, fixtures, furniture, mattresses, & decors. Featuring 3BR 2BA accommodating up to 8 ppl in a large & open living room & backyard, provided w/ multi-game table, bikes, kayaks, 6-burners grill, 2 mins walk to Sunset park, & Cabana Club access, it is the perfect Florida Keys getaway for your family.

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!

Waterfront House with 37 ft Dock & Cabana Club
Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

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.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Key Largo Waterfront: Tiki, Dock, Kayak & Pool
This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the tandem kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

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!!

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

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 house rentals in Islamorada
House rentals with a pool

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

Lagoon View Retreat • 2 Kings• Pickleball• Marina

Papo's Paradise

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

NEW! CASA LARGO -Golf Cart, 2 Kings 3 Bath, Kayaks

Waterfront home w/pool, dock & close to beach

Beach House, Private Pool & Dock, Gulf Sunset view

Waterfront Oasis with Boat Dock & Pool!
Weekly house rentals

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

Florida Keys Oceanside Utopia

Waterfront with Boat Lift/Kayaks and Hot Tub

Dock, Beach Club, Ocean & Gulf Access, Tennis

Oceanfront Rooftop Views w/ 75ft of Dockage

Tropical 2BR/2BA Getaway in Gorgeous Key Largo

Charming Beach House directly ON the beach

Marathon Keys Escape • Pool • Hot Tub • Near Beach
Private house rentals

Oceanside, Fee-Less Pet, with kayaks - 60 FT Dock

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

Heated Pool w/4 water loungers/CabanaClub/ 6 Bikes

Casa Chiquita Waterfront Canal Home

Waterfront Private Home w/Pool-Family&Pet Friendly

Chasing Sunrises | Family Style

Viamarhe House-Private beach, Kayak, yard games

Golf Coast Oasis near Sombrero Beach,
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $510 SGD | $561 SGD | $574 SGD | $574 SGD | $606 SGD | $632 SGD | $599 SGD | $561 SGD | $542 SGD | $542 SGD | $572 SGD | $584 SGD |
| 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 300 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $102 SGD per night before taxes and fees

Verified guest reviews
Over 1,900 verified reviews to help you choose

Family-friendly holiday rentals
280 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
180 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
290 of Islamorada holiday rentals include wifi 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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- House rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Long Beach
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Conch Key
- Theater of the Sea
- Everglades Alligator Farm
- Homestead-Miami Speedway
- Monkey Jungle
- Seven Mile Bridge
- Key Largo Kampground And Marina
- Dolphin Research Center
- Sunset Park
- Calusa Campground
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- Founder's Park




