Holiday rentals in Windley Key

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Welcome to Anglers Reef, a bright coastal cottage in Islamorada, FL, with access to resort-style amenities. Enjoy a private boat slip, tropical pool, sandy beach, and walkable marina. Inside, relax in open living spaces, a fully equipped kitchen, and serene bedrooms. Unwind on breezy porches or explore nearby snorkeling, fishing, dining, and Keys adventures. Ideal for families, couples, and boaters seeking laid-back luxury. Thoughtfully designed for comfort, privacy, and effortless island life.

Oceanfront 3‑Stories of Bliss • Dockage & Gameroom

🌴Welcome to Paradise Palms– the Crown Jewel of the Neighborhood🌴 This brand-new, gated oceanfront retreat offers an exclusive luxury experience in the Florida Keys. This three-story home blends modern elegance with tropical charm, featuring unobstructed panoramic ocean views, boat dockage, and luxury amenities designed for the ultimate getaway. Enjoy two oceanfront balconies and take in unforgettable sunrises and sunsets. We’re committed to providing the best—because you deserve nothing less.

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

FL Keys Ocean Front Escape

Welcome to FL Keys Ocean Front Escape in beautiful Islamorada! This 2-bedroom, 3-bathroom retreat offers stunning ocean views and all the comforts of home. Enjoy essentials like WiFi, air conditioning, a fully equipped kitchen, and a washer. Relax in paradise with the perfect blend of modern amenities and tropical charm. Experience 360' views of the finest Islamorada sunrise from the private roof top deck! Whether you're fishing, snorkeling, or just unwinding, your dream getaway starts here!

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

🌊Welcome to The Seascape🌊 Experience waterfront living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's famous sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

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.

Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!

Beautiful 4-bedroom, 3.5 bath home in gated community of Angler's Reef INCLUDES 31 FT boat slip. Renovated kitchen w/updated appliances, quartz countertops and breakfast bar. Downstairs Jr. suite (BED 1) with en-suite bathroom. Powder bath is located on the first floor off the kitchen and living area. The 8-person dining table and 5-person bar stools for large groups. This rental includes boat slip #14, which can accommodate boats up to 31 feet in length. Message for more information!

Angler’s Reef home • Pool • Kayaks • Paddle boards

Relax with the whole family at this peaceful Angler's Reef boutique complex. Oceanfront community located at Mile Marker 85 has a beautiful community pool overlooking the Atlantic ocean. The community also offer kayaks, which can be launch from the private beach. This home has 2 bedrooms located on the 2nd floor with their private bathroom. The kitchen is fully equipped with stainless appliances, granite counters, 3 TVs & WiFi. The property has parking for 2 vehicles. License 26-5143

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.