Windley Key Holiday Rentals

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Holiday Rentals in Windley Key

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

10.0 out of 10, Exceptional, (185)
"Lodgings first rate. Boat access to Mahi and Grouper catches."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

10.0 out of 10, Exceptional, (3)
"Our stay was nothing but amazing! The area/community is beautiful and Al was a wonderful host! Will definitely be staying here again next year!!"
FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

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, (513)
"Best kept secret, love staying here,!"
The price is AU$215
includes taxes & fees
15 Sept - 16 Sept
Breezy Palms Resort

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (100)
"Unique House boat experience, friendly staff. "
The price is AU$372
includes taxes & fees
2 Sept - 3 Sept
Treasure Harbor

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,038
includes taxes & fees
21 Aug - 22 Aug
The Islands of Islamorada

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (129)
"Clean, friendly, has its own beach"
Island Bay Resort

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"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, (221)
"Condo was clean and quiet. Loved the main suite in the back."
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

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

9.8 out of 10, Exceptional, (66)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

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

10.0 out of 10, Exceptional, (268)
"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....

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

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

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is AU$691
includes taxes & fees
21 Aug - 22 Aug
Charming Home in Key Largo

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (30)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

BEACHFRONT POOL HOME

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

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

9.6 out of 10, Exceptional, (55)
"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.

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

10.0 out of 10, Exceptional, (13)
"We had an amazing stay at this Key Largo condo! The location is ideal—very central to everything in the area. One of the highlights was having access to a golf cart, which made it easy and fun to explore the neighborhood and surrounding areas on local roads.The condo itself was clean, comfortable, and well-equipped. The beds were cozy, there were plenty of fresh towels, and the kitchen had all the essentials we needed. Each room had a smart TV, which was a great bonus for relaxing in the...
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities

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!!

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

9.4 out of 10, Exceptional, (73)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is AU$578
includes taxes & fees
25 Aug - 26 Aug
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
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