Windley Key Holiday Rentals

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Check prices for these dates

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Holiday Rentals in Windley Key

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Terrace/patio

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (495)
"Great Property, easy check in and "
The price is HK$604
HK$1,087 total
includes taxes & fees
17 Aug - 18 Aug
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (64)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is HK$4,278
HK$5,245 total
includes taxes & fees
1 Aug - 2 Aug
The Islands of Islamorada
Treasure Harbor
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (89)
"Very cute bost houses. Clean and quiet. "
The price is HK$911
HK$2,129 total
includes taxes & fees
17 Aug - 18 Aug
Treasure Harbor
Island Bay Resort
Private beach, sun-loungers, beach umbrellas, beach towels

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (125)
"Clean, friendly, has its own beach"
Island Bay Resort
Key Largo Cottages
Boating

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (22)
"Beautiful and peaceful place "
Key Largo Cottages
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (217)
"Great middle point to explore all the keys and relax and enjoy! "
The price is HK$1,413
HK$3,283 total
includes taxes & fees
31 Jul - 1 Aug
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
Marina

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

9.8 out of 10, Exceptional, (184)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!
Property grounds

Summer Deals! OCEANFRONT Lux 1300sf with 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."
The price is HK$1,900
HK$3,863 total
includes taxes & fees
28 Jul - 29 Jul
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (65)
"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Condo in the Keys
Outdoor pool

Condo in the Keys

5.0 star property
8.8 out of 10, Excellent, (9)
"Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. "
Condo in the Keys
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
Terrace/patio

Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach

9.8 out of 10, Exceptional, (129)
"The property is older but was clean and orderly. Good access to the rest of the city. First time staying in Key Largo so can’t gauge the property against others. "
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
BEACHFRONT POOL HOME
Outdoor pool, a heated pool

BEACHFRONT POOL HOME

9.6 out of 10, Exceptional, (106)
"Another fantastic stay in an amazing spot!!"
BEACHFRONT POOL HOME
Condo with Pool and Beach Access
Terrace/patio

Condo with Pool and Beach Access

9.8 out of 10, Exceptional, (22)
"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
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (70)
"Great tiny house, enjoyed our stay"
The price is HK$975
HK$2,964 total
includes taxes & fees
13 Aug - 14 Aug
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (57)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is HK$1,043
HK$3,032 total
includes taxes & fees
21 Aug - 22 Aug
Waterfront Tiny House w Pool, Beach, and Boat Dock
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (9)
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Outdoor pool, a heated pool

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (56)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Front desk girl i didn't remember her name but she was very kind and proffesional and gave us a beautiful upgrade. Our second time here and will continue to come back."
jonathan 1-night trip
Posted 1 day ago
Chesapeake Beach Resort