Holiday Rentals in Windley Key

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Our top choices for Windley Key holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is €317
includes taxes & fees
23 Mar - 24 Mar
Treasure Harbor

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (66 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is €273
includes taxes & fees
22 Mar - 23 Mar
Paradise in Key Largo, FL

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is €356
includes taxes & fees
13 Apr - 14 Apr
Amazing Ocean view condo

RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (24 reviews)
"Good stay"
Netherlands
Anna d.
The price is €294
includes taxes & fees
29 Mar - 30 Mar
RV by the Sea - Glamping in the Keys

Paradise in Key Largo Florida 2

Paradise in Key Largo Florida 2
Key Largo
9.6 out of 10, Exceptional, (44 reviews)
"The cleanliness, the availability, the comfort. Everything was perfect in fact. Vz are planning on contacting the owner and tomorrow maybe arrange another rental on that property. It was in the perfect spot walking distance to the pool. Everything was readily available. Everything that they advertised was actually above and beyond. Our expectations can't say enough. Good about it was a perfect vacation. Thank you"
United States
Steve V.
The price is €292
includes taxes & fees
14 Apr - 15 Apr
Paradise in Key Largo Florida 2

Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (16 reviews)
"Perfect weekend getaway location."
United States
Tex H.
The price is €322
includes taxes & fees
25 Mar - 26 Mar
Cozy place in Calusa Key Largo

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (112 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is €456
includes taxes & fees
6 Apr - 7 Apr
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (637 reviews)
"We enjoyed our stay! This was a better experience than the more expensive house one I paid in Key West. "
United States
Wendy
The price is €212
includes taxes & fees
29 Mar - 30 Mar
Breezy Palms Resort

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (7 reviews)
"Great area"
United States
Yesenia
The price is €421
includes taxes & fees
23 Mar - 24 Mar
Reel Key Largo Escape Ocean Pointe 5209

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (32 reviews)
"Clean, updated, had everything we could have asked for. "
United States
Debra D.
The price is €396
includes taxes & fees
29 Mar - 30 Mar
Charming Home in Key Largo

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.4 out of 10, Very good, (32 reviews)
"Clean room, Beautiful view of the sea from the room window."
United States
Serhiy
Kings Kamp

Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina

Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina
Key Largo
9.8 out of 10, Exceptional, (9 reviews)
"This is a beautiful place to stay. Convenient and quiet. Exceptionally well run. "
United States
Joleen
The price is €435
includes taxes & fees
31 Mar - 1 Apr
Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is €369
includes taxes & fees
27 Mar - 28 Mar
Island Sanctuary Islamorada

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (125 reviews)
"Beautiful place! My family enjoyed a wonderful vacation stay over Thanksgiving. Would highly recommend."
United States
Dan M.
Modern and Coastal Ocean Pointe 2307

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is €443
includes taxes & fees
17 Mar - 18 Mar
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (42 reviews)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is €411
includes taxes & fees
13 Apr - 14 Apr
Ocean view condo with balcony/marina view

Salty Mermaid Ocean Pointe 4406

Salty Mermaid Ocean Pointe 4406
Tavernier
10.0 out of 10, Exceptional, (1 review)
The price is €508
includes taxes & fees
25 Mar - 26 Mar
Salty Mermaid Ocean Pointe 4406

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (162 reviews)
"Very clean and quiet location. Beds were comfy and all necessities were provided. Would definately recommend!"
United States
Arielle F.
The price is €448
includes taxes & fees
14 Apr - 15 Apr
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
Key Largo
8.6 out of 10, Excellent, (90 reviews)
"It was very clean. Pet friendly. Everybody at the campground is wonderful."
United States
Tammie F.
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (1 review)
Premium Floating Bungalow by Stay Ombi
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

Find out more about Windley Key

Everything you need to know about Windley Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windley Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windley Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windley Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windley Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windley Key holiday rentals we have selected for you start as low as €212 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windley Key rentals

At Expedia, we put the best Windley Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windley Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windley Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windley Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.