Search Condos in Windley Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Condo Rentals in Windley Key

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....
Relax on the beach with a clear ocean view, lounge chairs, and a shaded area under a thatched-roof structure.

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....

10.0 out of 10, Exceptional, (267)
"We enjoyed our stay! It was a great condo and was exactly as described in the listing. "
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Relax by the pool surrounded by palm trees and lounge chairs.

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.6 out of 10, Exceptional, (54)
"This condo exceeded our expectations! It was immaculately clean and had a cozy, welcoming feel. The view was spectacular, offering a serene and beautiful backdrop. We had everything we needed, from kitchen essentials to comfy furniture, making our stay seamless and enjoyable. It’s the perfect spot for a relaxing escape. Highly recommend!"
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Relax by the resort's oval-shaped pool surrounded by palm trees and lounge chairs.

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

10.0 out of 10, Exceptional, (125)
"We had an excellent stay! The property and all the added touches made our stay relaxing and low stress. The host was engaging and helpful if we had questions. We would stay here again!"
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Relax by the pool surrounded by lush greenery and lounge under shaded umbrellas.

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (219)
"Condo was clean and quiet. Loved the main suite in the back."
The price is ￥26,449
￥60,576 total
includes taxes & fees
Aug 17 - Aug 18
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Enjoy waterfront views and access to the water from this property, surrounded by lush greenery and palm trees.

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (185)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Enjoy waterfront views and access to a dock and boat.

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

10.0 out of 10, Exceptional, (170)
"Very nice, close to the pool, nice amenities, close to tons of great food options."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Welcome to Paradise!
Relax in Adirondack chairs around a small table, overlooking the ocean.

Welcome to Paradise!

9.6 out of 10, Exceptional, (72)
"This one bedroom is in the Tower of Kawama a great central location on Key Largo. We enjoyed the ocean view as well as the pool area. We would certainly stay again. "
Welcome to Paradise!
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Relax on the beach with a thatched-roof hut and comfortable beach chairs.

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

9.6 out of 10, Exceptional, (204)
"Very nice place to stay."
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Condo with Pool and Beach Access
Relax on the deck overlooking the serene water with comfortable seating and a ceiling fan for a peaceful atmosphere.

Condo with Pool and Beach Access

10.0 out of 10, Exceptional, (21)
"We liked everything about the property. This is a quite end unit and was nicely finished. Would definitely highly recommend staying here."
Condo with Pool and Beach Access
Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities
Enjoy waterfront views and access to the sea from this property, which offers a dock and lush surroundings.

Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities

10.0 out of 10, Exceptional, (83)
"Everything was great with our stay and owner had great communication. This building also has a lot of activities for kids on the ground floor which was great. "
Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
Relax by the serene pool surrounded by lush greenery and tall palm trees.

Relaxed Boho Vibes & Views [ Ocean Pointe 2315]

9.8 out of 10, Exceptional, (172)
"Enjoyed our stay. Highlighted by day trips to Key West, snorkeling with Robbie’s, and seeing a manatee while kayaking in John Pennekamp State Park. Property has nice beach area and pool. "
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
LICENSED MGER - MODERN 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!
Relax in comfort with Adirondack chairs and a fire pit, overlooking the ocean.

LICENSED MGER - MODERN 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!

9.4 out of 10, Exceptional, (55)
"Very clean space. Great amenities, perfect for family. Host very easy to work with! "
LICENSED MGER - MODERN 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!
Amazing Sunset View in Key Largo
Relax by the pool surrounded by palm trees.

Amazing Sunset View in Key Largo

10.0 out of 10, Exceptional, (95)
"Property and facilities were as described. Host very responsive to our one enquiry. "
Amazing Sunset View in Key Largo
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Relax in two Adirondack chairs on a shaded deck overlooking the ocean.

Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!

9.6 out of 10, Exceptional, (287)
"Visited with my Mother, sister and cousin. Felt very safe with the gated security. The grounds were beautiful and very well maintained. Location was great! The beach, marina, pool were all very close by. And the condo was fabulous and very well stocked."
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!

10.0 out of 10, Exceptional, (39)
"We had a very nice stay - easy checkin, very clean condo unit, condo grounds were very clean with lots to do. Location was also nice - convenient to parks and restaurants. Would definitely recommend! "
Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Relax under the shade of this beachside structure, surrounded by comfortable seating and a stunning ocean view.

Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities

10.0 out of 10, Exceptional, (11)
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Relax by the ocean with a warm fire and comfortable seating.

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (151)
"We stayed for a week. Wonderful condo and resort."
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Luxury Condo at Ocean Front Kawama Tower Complex
Relax in a casual beachside seating area surrounded by a thatched-roof structure and Adirondack chairs.

Luxury Condo at Ocean Front Kawama Tower Complex

9.4 out of 10, Exceptional, (55)
"Very clean and spacious condo. Pool area very quiet and relaxing - no crowds. Enjoyed the pickle ball courts. Quick drive to restaurants."
Luxury Condo at Ocean Front Kawama Tower Complex
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
Relax by the resort's large pool surrounded by palm trees and lounge chairs.

Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball

10.0 out of 10, Exceptional, (31)
"Clean and easy to book. Great location for a nice fishing trip. Owner wonderful to work with and provide locale information that was very helpful. "
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Relax in a shaded seating area overlooking the water, surrounded by a thatched roof and comfortable benches.

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball

10.0 out of 10, Exceptional, (34)
"Great place to take your family and enjoy doing nothing but relaxing by the pool or on the beach. "
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windley Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"Great resort, excellent staff and customer service, I'll definitely coming back "
Jose 2-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort