Beachfront vacation rentals in Windley Key

Sunrise Escape - Ocean Front Villa - Sleeps 10

Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Anchors Away Condo - Key Colony Beach Oceanfront

Beautiful new renovation in Key Colony Beach ocean front complex. Unit #4 is a studio condo on the 1st floor (no stairs to climb) within steps of the heated pool and private beach. #4 features a crisp, clean white interior with new kitchen, bathroom and furnishings. Kitchen has everything needed to cook a complete meal (dishes, cookware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Beach Breeze

Be one of the first guest to stay at our new condo on the rare white sand private beach located in Key Colony Beach, FL. 2+2 ensuite, gourmet kitchen with designer touches. Patio table & chairs for outdoor dining and new Wicker upscale love seat & 2 chairs. Stackable washer & dryer in every unit. TV in living, primary & guest rooms. Paddle board, Kayak or swim right off of the beach or just sit and enjoy the beautiful view of the water. Pool is open. Minimum 7 days rental City Code.

Waterfront Oasis3/2 Direct Ocean

Welcome to our stunning vacation rental property located on the waters of the ocean, where you can enjoy the ultimate tropical getaway. Our property boasts of an exceptional location, featuring a private dock that provides direct access to the ocean. This beautifully furnished property has three spacious and comfortable bedrooms that can accommodate up to eight guests, making it perfect for families or friends. The two modern bathrooms are fully equipped with all the necessary amenities

Resort Condo: Pool | Beach | Marina | Pickleball

NEW LISTING! Experience the best of the Florida Keys in this prime location, offering both the luxurious amenities of a high-end resort and the cozy comforts of home, all with stunning views of the turquoise ocean. Enjoy access to an Olympic-size pool, hot tub, beautiful beach, marina, outdoor grills, tennis courts, pickleball, playground, and more. All of this comes at an excellent value, allowing you to spend more on the unforgettable experiences the Keys have to offer.

#1 Island Hideaway 89 - OCEAN FRONT

Enjoy the BEST VIEW from your living room window, 1st floor balcony and 2nd floor balcony directly overlook the Atlantic, marina and clubhouse. This 1 bedroom 1.5 bathroom is luxury and peaceful. Enjoy coffee in the captain's chairs on the balcony as the sun goes up or cocktails as the sun goes down. Custom kitchen bigger than most any other in this property, designer upgrades, professionally decorated. Enjoy the sitting area on the third floor overlooking the ocean.

Beachside Unit 22 - Private Beach on Atlantic

Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”