
House vacation rentals in Windley Key
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Top-rated house rentals in Windley Key
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OceanView 2/2.5 w Beach Pool & Marina Islamorada
Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional fee, if available. REELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal.

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!!!

Exceptional vaca in Angler's Reef Islamorada
Welcome to 128 Anglers Way: "Morada Daydreaming". This house has 2 bedrooms upstairs, each with its own full bath and private balcony. A washer/dryer combo is conveniently located upstairs. The main level open floor plan features peek a boo ocean views. It also contains a half bath and a fully stocked kitchen. An outdoor seating area and gas grill is provided. Includes 2 assigned parking spaces. Angler's Reef is a premier resort style community with a heated pool, kayaks, and paddle boards.

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.

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
This unique property possesses easygoing charm & has been in the family since 1951. It was purchased by owners’ grandparents to use as a fishing cottage. It has since evolved, creating a classic Keys Conch house. (CONCH is a term used to describe a Florida Keys native & is derived from shell found in local waters). Guests enjoy 1 acre of waterfront privacy surrounded by coconut palms & endless bay front views and offers spectacular sunsets, wildlife encounters, & direct boating access.

Blue House Marine in Key Largo
If it’s for a company, I need to be notified which I do not wish to have any company allowed to booked. 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 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.

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.

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.

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!

Pristine Islamorada Pool Home with Ocean View and
Welcome to Angler’s Reef 148 - a stunning Islamorada vacation destination. This two bedroom, two and a half bath conch house overlooks the resort style swimming pool and is available for weekly and monthly vacation rentals. Our home has ocean views, 2 spacious decks, a full kitchen, dock space is available to rent - check prior to booking and other inspired amenities for your best vacation yet!
Popular amenities for Windley Key house rentals
House rentals with a pool

Heart of Islamorada ~ Private Boat Dockage

Beach House in Marathon with Amazing Backyard!

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Lagoona-Matata

Beach House, Private Pool, Dock, Gulf View Sunsets

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Las Olas

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks
Weekly house rentals

Florida Keys Retreat

Off The Charts-Waterfront Tiki Bar & Private Dock

3/2 Home w Dock, lagoon, kayaks!

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Luxury Waterfront Home

Waterfront Key Largo Home - Tropical Paradise

Luxury Boating Paradise+Pool+Sailing Kayaks

Gorgeous Ocean View Home!
Private house rentals

Blue Heaven Marathon

World-Class Oceanfront Pool/Hottub Sunset Escape

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

P87 - Modern 4 bedroom, 4 bath home on open water

Cottage in Paradise

Golf Coast Oasis near Sombrero Beach

The Islander 3BR Pool Oasis in Key Colony- KCB#1

Villa 7205 on Duck Key- Boat Slip Available
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Schnebly Redland's Winery & Brewery
- Calusa Campground
- Coral Castle
- Homestead-Miami Speedway
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Theater of the Sea
- Seven Mile Bridge
- Everglades Alligator Farm
- Deering Estate
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Founder's Park
- History Of Diving Museum
- Conch Key





