Holiday rentals in Windley Key

Top guest favourite

Guest favourite

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.

Top guest favourite

Guest favourite

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.

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.

Top guest favourite

Guest favourite

Closest Oceanfront Home - 3 Stories and Boat Dock

Welcome to Paradise Palms, the crown jewel of oceanfront living in Islamorada. This gated, three-story retreat is one of the closest homes to the water, offering unobstructed panoramic views, rare third-floor balcony access, and boat dockage. Thoughtfully designed with modern coastal elegance, enjoy two oceanfront balconies, luxury amenities, and unforgettable sunrises and sunsets. Your comfort and satisfaction are our top priorities. Let us help you turn your vacation dreams into reality.

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

Top guest favourite

Guest favourite

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.

Top guest favourite

Guest favourite

Luxury Island Retreat • Speakeasy Lounge & Dock

"It's just the best AirBnB we have ever seen...beyond what we have had!" - Guest Oceanfront retreat for families, groups & special occasions: 🍸 Speakeasy for cocktails & karaoke 🏊 Community pool & paddleboarding from private dock 🚴 4 bikes to explore 🌅 Ocean views from 2nd & 3rd-floor balconies 🔥 BBQ & fire pit for intimate gatherings 🍳 Well-appointed kitchen 🛏️ 3 bedrooms, ensuite baths & luxury linens 🔋 EV charger 📍 Paddleboard to Islamorada Sandbar 💬 24/7 guest support

Top guest favourite

Guest favourite

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.

Top guest favourite

Guest favourite

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

Top guest favourite

Guest favourite

Las Olas: waterfront home, private pool & dock

Experience Key Largo from this beautiful waterfront home, perfect for families and groups of up to 8 guests. Relax by the private pool, enjoy the dock, play a game of pool, or unwind in the spacious outdoor living areas and balconies. The home features a modern kitchen, comfortable living spaces, and everything you need for an unforgettable Florida Keys getaway. The perfect place to enjoy the sunshine, waterfront lifestyle, and quality time with family and friends.

Off-Grid Islamorada Houseboat

Escape to your own private floating retreat in Islamorada, surrounded by nature and endless starry skies. This off-grid houseboat offers total seclusion—no neighbors, just peace and beauty. Perfect for nature lovers and stargazers. Please note: Guests may arrive on their own vessel or boar rental options are available, dock access is 200 yards from our mooring. Enjoy unmatched tranquility in the heart of the Florida Keys. Minimum stay 2 nights.

Top guest favourite

Guest favourite

Fishing Getaway | Dock, Pool & Sunrise

Wake up to breathtaking oceanfront sunrises in the Sportfishing Capital of the World. This luxury 3BR, 3BA townhome in Islamorada features a private dock, waterfront resort-style pool, and a quiet gated community just minutes from the Keys’ best fishing, marinas, restaurants, and attractions. Pet-friendly and fully equipped, it’s the perfect escape for anglers, families, couples, and extended stays.