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Beach house holiday rentals in Islamorada

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Top-rated beach 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

Guest favourite

Home in Marathon

5 out of 5 average rating, 21 reviews

Horizon

Horizon is a bright beautiful upscale home, custom designed to take full advantage of its unique ocean location. Every room, has a wide sliding glass door to oceanfront balconies. Every bedroom has a private bath. Pool with Spa, Observation Platform for those sunrises on open water, ping pong, corn toss, kayaks and paddle boards, multiple dining areas, WIFI, quality appliances, comfy cotton bedding, crib, high chair multiple TV's poolside loungers, rocking chairs & bird watching. ++++

Guest favourite

Home in Islamorada

5 out of 5 average rating, 36 reviews

Beautiful Anglers Reef - 2/2.5 - Pool+Marina+Beach

Slip available for rent 6/22/24 & 7/20/24. DM for details Sat - Sat preferred, inquire as needed Awesome family get-a-away in beautiful Islamorada. The Oceanfront pool is serene! The gated community is an immaculately kept flora fauna setting. Located in walking distance to swim with the dolphins at Theater of the Sea and local restaurants and bars. Anglers Reef is perfect for boaters, kayaker's, foodies, honeymooners, couples, snowbirds or anyone that wants to experience the Florida Keys.

Guest favourite

Home in Key Largo

5 out of 5 average rating, 23 reviews

Private 2+ Acre House~Private Beach~Tiki Hut~Dock

There is nothing like this tropical waterfront property in Key Largo. This unique large acre lot offers crystal clear water, dock access, a tiki hut, room for your boat and even a small boat ramp. You will truly feel like you are in your own slice of tropical paradise! Relax in a hammock, on your own private beach, or under the giant screened patio. If you are up for an adventure use our paddle boards and kayaks located on the property. We are located on the bayside for the perfect sunsets!

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 178 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.

Guest favourite

Home in Key Largo

4.97 out of 5 average rating, 103 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! 🏝️😊

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 121 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.

Guest favourite

Home in Key Largo

4.87 out of 5 average rating, 109 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

Close to restaurants and dining, parks, and great views. You’ll love my home because of the peaceful atmosphere, sitting on your own dock watching the boats pass by or friendly manatees swim up. Enjoy swimming in the pool or just relaxing on the patio with a drink in your hand. This home is in a private, gated community and about 10 homes from the bay. A Pontoon boat rental is available(ask for details). Great for couples, adventurers, families (with kids).

Guest favourite

Home in Duck Key

4.93 out of 5 average rating, 145 reviews

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Welcome to your happy place in paradise! 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!!

Guest favourite

Home in Marathon

5 out of 5 average rating, 24 reviews

Oceanfront w/ Dock, Hot Tub & Secluded

Buchanan Keys Cottage Take a step back into “Old Keys” living. Once Upon A Tide; there was a sense of tranquility & peacefulness found throughout the Keys, like the one you will uncover when choosing to stay at this private, serene, 1/1 oceanfront cottage. Located on Grassy Key, this beautiful home is just 10 minutes from the City of Marathon. Far enough to be away from the hustle & bustle, but close enough to make a grocery/store run a “Keys breeze”.

Guest favourite

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

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 81 reviews

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!

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Popular amenities for Islamorada beach house rentals

Free parking on premises

Air conditioning

Beachfront house rentals

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 25 reviews

Florida Keys Oceanside Utopia

Guest favourite

Home in Marathon

5 out of 5 average rating, 11 reviews

Seaside Sunrise. Newly remodeled waterfront

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 8 reviews

Key Colony Beach-POOL & DOCK

Guest favourite

Home in Key Largo

4.95 out of 5 average rating, 43 reviews

Treetops

Guest favourite

Home in Marathon

5 out of 5 average rating, 70 reviews

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

Home in Marathon

5 out of 5 average rating, 7 reviews

Oceanside Oasis 2bed/2bath with brand new private

Guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 19 reviews

Water, Water Everywhere! "The Wheel House"

Beach house rentals with a pool

Guest favourite

Home in Marathon

5 out of 5 average rating, 18 reviews

Waterfront Escape -VACA-23-408

Home in Marathon

5 out of 5 average rating, 8 reviews

Salty kisses beach house

Guest favourite

Home in Marathon

5 out of 5 average rating, 24 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

Guest favourite

Home in Marathon

5 out of 5 average rating, 14 reviews

Waterfront 2-bedroom Home w/New Pool and Spa

Home in Key Largo

4.88 out of 5 average rating, 188 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Home in Key Largo

4.9 out of 5 average rating, 77 reviews

Great key Largo home with water front and pool

Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 22 reviews

Cielo's Del Mar 1 - Pool/Dock/Beach Luxury in KCB

Private beach house rentals

Guest favourite

Home in Marathon

5 out of 5 average rating, 27 reviews

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

Guest favourite

Home in Marathon

4.83 out of 5 average rating, 18 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 63 reviews

Florida Keys Cottage with Pool - Hawks Cay Resort

Guest favourite

Home in Key Largo

4.89 out of 5 average rating, 19 reviews

Keys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More

Guest favourite

Home in Key Largo

5 out of 5 average rating, 37 reviews

Coastal Cottage with private backyard and hot tub

Guest favourite

Home in Marathon

4.88 out of 5 average rating, 33 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

Home in Islamorada

4.84 out of 5 average rating, 25 reviews

Hidden Gem Duplex in Heart of Islamorada! Sleeps 8

Home in Key Largo

5 out of 5 average rating, 7 reviews

Cozy home with beach access and 2 boat ramps

Destinations to explore