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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

Our top choices for Windley Key resorts

Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, individually decorated

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (212 reviews)
"Room was beautiful, just as pictured on the website. It is a lovely place."
United States
CATHY
The price is AED 1,027
AED 1,424 total
includes taxes & fees
7 Jul - 8 Jul
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,322 reviews)
"It was amazing place, highly recommend, thdy have really good view☺️"
United States
Tuba
The price is AED 475
AED 699 total
includes taxes & fees
23 Jun - 24 Jun
Lime Tree Bay Resort
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,320 reviews)
"Perfect couple stay"
United States
Yiset
The price is AED 756
AED 1,119 total
includes taxes & fees
14 Jul - 15 Jul
Cheeca Lodge & Spa
Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,287 reviews)
"Good place to stay, very friendly staff and great breakfast!"
United Kingdom
Christos
The price is AED 598
AED 941 total
includes taxes & fees
6 Jul - 7 Jul
Amara Cay Resort
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Our favorite hotel in the FL Keys"
United States
Jose
The price is AED 1,090
AED 1,428 total
includes taxes & fees
25 Jun - 26 Jun
Playa Largo Resort & Spa, Autograph Collection
Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,003 reviews)
"Our families really enjoyed our stay there new favorite"
United States
Marc
The price is AED 674
AED 1,027 total
includes taxes & fees
9 Jul - 10 Jul
La Siesta Resort & Villas
Exterior

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,103 reviews)
"Great stay over Spring Break. Beautiful place!"
United States
Angela
The price is AED 931
AED 1,250 total
includes taxes & fees
12 Jul - 13 Jul
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
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Top Windley Key Hotel Reviews

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Bayside Inn Key Largo was one of the highlights of our Florida Keys vacation. From the moment we arrived, it felt like the perfect welcome to the Keys. The property sits right on the bay and offers so many relaxing amenities packed into a small, easy to navigate resort. There is a small beach area, paddle boards, hammocks, picnic tables, lounge chairs, and even a dock overlooking the water that is perfect for watching the sunset or simply relaxing in the sun. One of my favorite memories was waking up each morning to the sound of roosters, grabbing a coffee from the fantastic self serve coffee station in the lobby, and walking down to the dock to watch the sunrise over the water. The location couldn’t be better. Snook’s Restaurant is literally next door, making it easy to walk over for breakfast, lunch, dinner, drinks, or sunset views. You can spend the day paddle boarding, swimming, sightseeing, or simply relaxing by the water without ever needing to get back in your car. Our room was clean, comfortable, and well maintained, with a comfy bed, a nice bathroom, and beautiful views of the bay. The front desk hostess was incredibly kind and helpful, making us feel welcome throughout our stay. What I loved most was that Bayside Inn doesn’t try to be a giant luxury resort. It’s small, relaxed, and unpretentious while still offering wonderful amenities and an authentic Keys atmosphere. If you’re looking for a peaceful waterfront getaway in Key Largo, this is it."
Trici 2-night trip
Posted 2 hours ago
Bayside Inn Key Largo