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House vacation rentals in Islamorada

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Top-rated house rentals in Islamorada

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Home in Key Largo

4.84 out of 5 average rating, 428 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, totally renovated home with large TV’s, spacious living area, 2 Large Balconies including roof top great for star gazing, all the amenities of home. Free use of kayaks at the house, Kayak John pennekamp state park steps away from front door. 27 foot boat available 4 all water activities Which I captain.Quiet private street close to all keys activities and restaurants. There is a downstairs space that on a very rare occasion is occupied by myself or family member

Home in Key Largo

4.96 out of 5 average rating, 124 reviews

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!

Home in Key Largo

4.99 out of 5 average rating, 149 reviews

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Home in Islamorada

4.97 out of 5 average rating, 177 reviews

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.

Home in Marathon

4.94 out of 5 average rating, 158 reviews

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!!

Home in Key Largo

4.97 out of 5 average rating, 101 reviews

Little Cottage on an island

Very nice quiet neighborhood. Clean updated home with new appliances. Owner does live on property. There is a shared washer/dryer outside. The house is fully furnished with a queen bed and pullout sofa bed twin size. The home has a beautiful little office to work in and a full kitchen with all dishes and cooking utensils. Centrally located in Key Largo... 1 mile away from everything you need! There is a 21 yrs and over policy - house does have liquor bar. Thank you! 🏝️😊

Home in Marathon

4.99 out of 5 average rating, 120 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Home in Marathon

4.98 out of 5 average rating, 48 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Home in Key Largo

4.91 out of 5 average rating, 148 reviews

Blue House Marine in Key Largo

The house is a Duplex style house for guest it is very quite and private it has 3 bedrooms and two bathrooms kitchen living room and dining area also a walk around balcony its screen in, it has 2 queen style beds and two twin beds. the home has been remodel you have canal views and open ocean viewsfull bathroom by the pool, barbecue area table and chairs for dining plus out door furniture. P.S There is no longer pool heating

Home in Key Largo

4.9 out of 5 average rating, 374 reviews

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.

Home in Duck Key

4.9 out of 5 average rating, 162 reviews

4 Bed Sanctuary Villa w/ 35 ft Dock & Private Pool

My place is close to the heart of the FL keys. You’ll love my place because of the private tranquil pool in the backyard!. My place is good for couples, business travelers, families (with kids), and big groups. We also have a 35 foot dock that comes with the rental of the villa. You will need to procure trailer parking at Grassy Key Marina 2 miles South of the villa.

Home in Marathon

4.98 out of 5 average rating, 132 reviews

Marathon one-level home on the Marina - with slip!

***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.

Vacation rentals for every style

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Popular amenities for Islamorada house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Marathon

5 out of 5 average rating, 27 reviews

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

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Home in Marathon

4.95 out of 5 average rating, 124 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Home in Marathon

4.98 out of 5 average rating, 40 reviews

Oceanfront with Pool near Sombrero Beach

Home in Key Largo

4.88 out of 5 average rating, 188 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Home in Key Largo

4.95 out of 5 average rating, 111 reviews

Mariners Club Resort, Best in the Upper Keys

Home in Key Largo

4.87 out of 5 average rating, 109 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

Home in Marathon

5 out of 5 average rating, 8 reviews

Salt & Seaglass. XL Screen Porch, Dock, Pool club!

House rentals with free parking

Home in Marathon

5 out of 5 average rating, 36 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Home in Key Largo

4.96 out of 5 average rating, 51 reviews

Casa Solaris | Key Largo home with Private Pool!

Home in Marathon

5 out of 5 average rating, 30 reviews

Luxury Boating Paradise+Pool+Steps to Snorkeling

Home in Marathon

5 out of 5 average rating, 70 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

Home in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Home in Key Largo

4.92 out of 5 average rating, 64 reviews

Ocean Breeze Home

Home in Marathon

5 out of 5 average rating, 8 reviews

*NEW!*Serenity Oasis~Kayaks~Bikes!~Hot Tub~Spa!

Home in Marathon

5 out of 5 average rating, 20 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Weekly house rentals

Home in Key Largo

5 out of 5 average rating, 3 reviews

Keys Home, Boat Slip + Golf Cart

Home in Marathon

4.98 out of 5 average rating, 59 reviews

Sombrero beach oasis,great location,many amenities

Home in Marathon

4.98 out of 5 average rating, 82 reviews

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

Home in Marathon

4.93 out of 5 average rating, 15 reviews

4BR Sombrero Beach House on Canal w Dock & Pool

Home in Marathon

5 out of 5 average rating, 21 reviews

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

Home in Marathon

4.98 out of 5 average rating, 42 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Home in Marathon

5 out of 5 average rating, 18 reviews

Off the Hook~ Luxe Pool Home, Kayaks & Bikes!

Home in Key Largo

4.98 out of 5 average rating, 83 reviews

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.

Quick stats about house rentals in Islamorada

Total rentals
310 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
300 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
190 properties have a pool

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