Windley Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation 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

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (195)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

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 CA $107
CA $192 total
includes taxes & fees
Sep 15 - Sep 16
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 CA $125
CA $336 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $763
CA $935 total
includes taxes & fees
Aug 22 - Aug 23
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (130)
"Clean, friendly, has its own beach"
Island Bay Resort

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, (186)
"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

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is CA $237
CA $615 total
includes taxes & fees
Aug 22 - Aug 23
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

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

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.

Welcome to Paradise!

9.6 out of 10, Exceptional, (72)
"This one bedroom is in the Tower of Kawama a great central location on Key Largo. We enjoyed the ocean view as well as the pool area. We would certainly stay again. "
Welcome to Paradise!

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

10.0 out of 10, Exceptional, (1)
"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windley Key Hotel Reviews