Windley Key Vacation Rentals

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Vacation Rentals in Windley Key

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

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

2.5 star property
8.8 out of 10, Excellent, (497)
"Great Property, easy check in and "
The price is CA $111
CA $196 total
includes taxes & fees
Aug 17 - Aug 18
Breezy Palms Resort

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 CA $756
CA $926 total
includes taxes & fees
Aug 3 - Aug 4
The Islands of Islamorada

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (89)
"Very cute bost houses. Clean and quiet. "
The price is CA $159
CA $373 total
includes taxes & fees
Aug 10 - Aug 11
Treasure Harbor

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (126)
"Clean, friendly, has its own beach"
Island Bay Resort

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

9.8 out of 10, Exceptional, (217)
"Great middle point to explore all the keys and relax and enjoy! "
The price is CA $274
CA $605 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

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

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

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."
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!

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

Charming Home in Key Largo

9.8 out of 10, Exceptional, (22)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is CA $112
CA $450 total
includes taxes & fees
Aug 4 - Aug 5
Charming Home in Key Largo

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

9.8 out of 10, Exceptional, (130)
"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

9.6 out of 10, Exceptional, (106)
"Another fantastic stay in an amazing spot!!"
BEACHFRONT POOL HOME

Key Largo Sunset Estate

10.0 out of 10, Exceptional, (56)
"We loved our stay! Plenty of room for all of us, amazing view, beautiful sunsets, and live music every night."
Key Largo Sunset Estate

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

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

9.4 out of 10, Exceptional, (70)
"Great tiny house, enjoyed our stay"
The price is CA $166
CA $507 total
includes taxes & fees
Aug 25 - Aug 26
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Kings Kamp

2.5 star property
8.6 out of 10, Excellent, (22)
"The property is beautiful, nicely renovated and clean. A true gem is a covered patio with grill and a small beach right outside the door. There is plenty of local attractions to choose from near by. We had a fantastic stay and would highly recommend this property. We hope to come back again some day. Thank you!"
The price is CA $256
CA $289 total
includes taxes & fees
Aug 29 - Aug 30
Kings Kamp
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