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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Villas in Windley Key

The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (63)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is NZ$1,113
includes taxes & fees
1 Aug - 2 Aug
The Islands of Islamorada
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
Boats docked in a serene marina surrounded by lush greenery and palm trees.

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (51)
"Great location Vivian was very responsive to any questions we had"
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
Stroll through a serene outdoor space surrounded by mature trees and a variety of shrubs, featuring a large rock and a red pathway.

SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!

9.4 out of 10, Exceptional, (30)
"We enjoyed the condo and grounds."
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
2bd/2ba Ocean Retreat in Kawama Yacht Club
Enjoy al fresco dining and relaxation in this shaded patio area, complete with a barbecue grill and comfortable seating.

2bd/2ba Ocean Retreat in Kawama Yacht Club

10.0 out of 10, Exceptional, (41)
"Property was everything as advertised. Check in / out was a breeze. Located directly beside cabana and pool areas. The lagoon was a nice surprise for snorkeling. The property is close to shopping and everything in Key Largo. Definitely recommend for a family adventure."
2bd/2ba Ocean Retreat in Kawama Yacht Club
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
Relax by the tranquil pool surrounded by a natural rock formation and a marina with docked boats.

SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

9.6 out of 10, Exceptional, (66)
"Our unit was super clean and met all of our needs We enjoyed how big the place was and the overall property had plenty for us to do! Great location too"
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
Waterfront House with Boat Dock
Relax on the spacious balcony with a sofa set and individual chairs, overlooking a serene landscape.

Waterfront House with Boat Dock

5.0 star property
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
Waterfront House with Boat Dock
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Overlooking the marina, this hotel features a stunning rock formation with a cascading water feature.

MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!

9.6 out of 10, Exceptional, (42)
"We had a really wonderful stay at the property. The place is very clean, very well maintained and came equipped with everything we needed. The pool and facilities are perfect. The only complaint (and it is super minor) is that there isn’t a beach close by so we travelled a good distance to find one, not that we minded since it meant we got to explore the Keys."
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Guests can enjoy a serene atmosphere and stunning views of the pool and garden from this resort's two-story building.

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

10.0 out of 10, Exceptional, (1)
"This was a beautiful spot for 3 couples to relax and enjoy this beautiful setting. The outside space was perfect with tables, firepit & grills. The house was stocked well enough to be able to prepare some meals. I would definitely return again."
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Enjoy a serene ocean view from the resort's pool, surrounded by lush greenery and palm trees.

Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

10.0 out of 10, Exceptional, (13)
"Anglers Way was a meticulously clean property centrally located on Islamorada. The hosts were extremely responsive to our inquiries prior to and during our stay in their home. The property was well equipped and provided for all our needs. They undoubtedly deserve our 5 star review and would recommend this property for those seeking a restful vacation. "
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
The Lookout with Resort Privileges
Relax by the resort pool surrounded by palm trees and lounge chairs.

The Lookout with Resort Privileges

The Lookout with Resort Privileges
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Stunning two-story residence with a balcony and beautiful garden views.

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

9.4 out of 10, Exceptional, (60)
"Easy clean condo "
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Relax by the ocean-view pool surrounded by lounge chairs and a shaded pavilion.

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (115)
"The property and the location was absolutely perfect. "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Relax by the tranquil pool, surrounded by lush greenery and a serene waterfront setting.

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

10.0 out of 10, Exceptional, (2)
"We’ve vacationed in the Keys many times and this property was the best. First is location. It’s on a canal cut off Little Basin. There are many walkable restaurants and attractions. The house itself was very clean and the layout conducive to renters with two master suites upstairs and a smaller bedroom and bath down. Property management very attentive and communicative with a very nice young lady coming on site. Beautiful pool area and deck by water. Can’t go wrong with this."
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Newly upgraded Key Largo Villa W/Boat Slip
Relax on the patio surrounded by palm trees and a serene body of water.

Newly upgraded Key Largo Villa W/Boat Slip

10.0 out of 10, Exceptional, (81)
"Excellent location Great value"
Newly upgraded Key Largo Villa W/Boat Slip
Sandcastle Luxury Villa in Key Largo with Resort Privileges
Relax by the pool surrounded by palm trees and lounge chairs, with a picturesque arched bridge connecting the area.

Sandcastle Luxury Villa in Key Largo with Resort Privileges

10.0 out of 10, Exceptional, (3)
"The house was great and so was the resort access. Enjoyable long weekend!"
Sandcastle Luxury Villa in Key Largo with Resort Privileges
Endless Summer with Resort Privileges
Relax by the pool surrounded by palm trees and lounge chairs, with a picturesque arched bridge connecting the area.

Endless Summer with Resort Privileges

9.6 out of 10, Exceptional, (14)
"Great location. Everyone was very attentive. They went beyond during our stay and after. Resort is such a bonus. I've been a serval times and i highly recommend the property"
Endless Summer with Resort Privileges
Sea Haven with Resort Privileges
Relax by the resort's central pool, surrounded by palm trees and lounge areas, with a picturesque arched bridge connecting the spaces.

Sea Haven with Resort Privileges

9.8 out of 10, Exceptional, (9)
"Place was clean. Shuttle from house to resort was quick & reliable. Resort very nice."
Sea Haven with Resort Privileges
Gull's Nest with Resort Privileges
Relax by the ocean with a clear view from this resort's pool area, surrounded by lounge chairs and lush greenery.

Gull's Nest with Resort Privileges

9.6 out of 10, Exceptional, (24)
"Not far from miami airport. Great resort access. Beautiful and clean lodging. Food is also great as resort. Will rebook! "
Gull's Nest with Resort Privileges
Coastal Oasis with Resort Privileges
Relax by the pool surrounded by palm trees and lounge chairs under a picturesque arched bridge.

Coastal Oasis with Resort Privileges

9.4 out of 10, Exceptional, (6)
"Excellent in every way … clean , new and beautiful place !!"
Coastal Oasis with Resort Privileges
Twilight with Resort Privileges
Relax by the pool surrounded by palm trees and lounge chairs, with a picturesque arched bridge connecting the area.

Twilight with Resort Privileges

10.0 out of 10, Exceptional, (1)
"What a great option to have access to the hotel but come back each day and finish at the clubhouse pool for sunset! Really great house with plenty of room and great variety to get away from the hotel! "
Twilight with Resort Privileges
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Delightful stay. Lovely pool areas. Lot of activities included in Hotel Fee including par 3 golf, kayaking, fishing off the pier. Food service was excellent, with the freshest fruit we've every had !!"
Jerry 4-night trip
Posted 1 day ago
Cheeca Lodge & Spa