House vacation rentals in Windley Key

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.

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.

Life On A Rock Luxury Home in Downtown Islamorada

This Tommy Bahama Inspired Home Located at Mile Marker 81. Restaurants, Bars, Shops, and Beach all Walkable in this location. Located in the Heart of Downtown Islamorada. If you need specific dates please reach out to us. The Home features all Tommy Bahama Furniture, New Tempur-Pedic Breeze Mattresses. If you need specific dates please reach out to us. Room for Boat / Trailer Storage Perfect Biking Location Full Kitchen Washer / Dryer 65 Inch TV in Living Room Wifi Natural Light House

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.

Off The Charts-Waterfront Tiki Bar & Private Dock

Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets. For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.

Two Authentic Conch Houses Private Beach on FL BAY

Looking for the perfect Florida Keys vacation rental? Nestled between Key Largo and Islamorada, Sunset Beach Hideaway is a unique waterfront retreat directly on the Florida Bay. Set on 1.16 acres of lush tropical landscaping with coral rock block fences, this private getaway blends Old Florida charm with modern comforts. 📍 Conveniently located in Tavernier, Florida, just steps from Circle K and Dairy Queen. 🎥 Watch the video tour: Sunset Beach Hideaway

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!

El Encanto | Private pool & tropical tiki

Your tropical Key Largo escape: a private pool, shaded tiki, grill, and generous outdoor areas made for time together. El Encanto welcomes up to 8 guests with 3 queen bedrooms, a sofa bed, 2 bathrooms, an equipped kitchen, bright living room, dining area, laundry, and on-site parking. Unwind by the water, share an outdoor meal, and return to a cool, comfortable home prepared for families and friends.

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!