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House vacation rentals in Windley Key

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Top-rated house rentals in Windley Key

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Home in Key Largo

4.84 out of 5 average rating, 429 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, 126 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, 151 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, 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.

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, 104 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, 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.

Home in Key Largo

4.97 out of 5 average rating, 144 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

WATERFRONT Oceanside Keys delight In Key Largo Kampground- minimum stay 4 days. Your own private TIKI/ BOAT DOCK & swim ladder at the door; HOA boat launch. Bring or rent a boat up to 25' [ no jet skis] Snorkel in front of the house. Launch the PROVIDED tandem kayak from our beach down the street. 1 mile from the land base of Pennekamp State Park. Paddling, boating, fishing, snorkeling and diving are glorious in Pennekamp Park waters. No indoor smoking. No pets.

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).

Home in Key Colony Beach

4.93 out of 5 average rating, 101 reviews

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.

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, 375 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.

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Popular amenities for Windley Key house rentals

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House rentals with a pool

Home in Marathon

5 out of 5 average rating, 36 reviews

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

Home in Marathon

5 out of 5 average rating, 17 reviews

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

Home in Marathon

4.98 out of 5 average rating, 53 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Home in Key Largo

4.88 out of 5 average rating, 188 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Home in Key Largo

4.96 out of 5 average rating, 51 reviews

Casa Solaris | Key Largo home with Private Pool!

Home in Marathon

4.93 out of 5 average rating, 28 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

Home in Marathon

5 out of 5 average rating, 18 reviews

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

Home in Marathon

4.98 out of 5 average rating, 132 reviews

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

Weekly house rentals

Home in Marathon

5 out of 5 average rating, 18 reviews

Waterfront Escape -VACA-23-408

Home in Marathon

4.91 out of 5 average rating, 11 reviews

1 Free Night-Ask Us How - Tropical Private Home

Home in Marathon

5 out of 5 average rating, 27 reviews

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

Home in Marathon

4.98 out of 5 average rating, 41 reviews

Oceanfront with Pool near Sombrero Beach

Home in Key Largo

4.91 out of 5 average rating, 68 reviews

Little Peace of Haven

Home in Key Largo

4.9 out of 5 average rating, 77 reviews

Great key Largo home with water front and pool

Home in Marathon

5 out of 5 average rating, 70 reviews

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

Home in Key Largo

4.95 out of 5 average rating, 43 reviews

Treetops

Private house rentals

Home in Marathon

4.96 out of 5 average rating, 25 reviews

Florida Keys Oceanside Utopia

Home in Key Largo

4.89 out of 5 average rating, 19 reviews

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

Home in Key Largo

5 out of 5 average rating, 37 reviews

Coastal Cottage with private backyard and hot tub

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

Home in Key Colony Beach

5 out of 5 average rating, 75 reviews

“La casa azul” step 3’ to a private pool

Home in Marathon

4.88 out of 5 average rating, 17 reviews

Viamarhe House-Private beach, Kayak, yard games

Home in Key Colony Beach

4.95 out of 5 average rating, 19 reviews

Water, Water Everywhere! "The Wheel House"

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