A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Windley Key Vacation Rentals

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Our top choices for Windley Key vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (783 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $172
CA $216 total
includes taxes & fees
Nov 17 - Nov 18
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (182 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is CA $139
CA $355 total
includes taxes & fees
Nov 11 - Nov 12
Treasure Harbor

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is CA $174
CA $508 total
includes taxes & fees
Nov 15 - Nov 16
Florida Keys Getaway - Slps 4 - Ocean View

4. Paradise Palms | 2 Balconies | Ocean Pointe 1206

Paradise Palms | 2 Balconies | Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is CA $243
CA $616 total
includes taxes & fees
Nov 14 - Nov 15
Paradise Palms | 2 Balconies | Ocean Pointe 1206

5. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (42 reviews)
"It was very nice!!"
United States
Michelle
The price is CA $422
CA $474 total
includes taxes & fees
Dec 10 - Dec 11
Kings Kamp

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is CA $177
CA $511 total
includes taxes & fees
Nov 15 - Nov 16
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

7. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is CA $270
CA $635 total
includes taxes & fees
Nov 16 - Nov 17
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

8. Heavenly Hideaway | Ocean View | Ocean Pointe 3306

Heavenly Hideaway | Ocean View | Ocean Pointe 3306
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Second time staying in this condo. Great view, clean, and really like the interior design. Looking forward to visiting again next year."
United States
Doug M.
The price is CA $275
CA $671 total
includes taxes & fees
Nov 18 - Nov 19
Heavenly Hideaway | Ocean View | Ocean Pointe 3306

9. Corner Penthouse | Ocean Views | Ocean Pointe 5416

Corner Penthouse | Ocean Views | Ocean Pointe 5416
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great place - love the location! "
United States
Ann C.
The price is CA $384
CA $803 total
includes taxes & fees
Nov 10 - Nov 11
Corner Penthouse | Ocean Views | Ocean Pointe 5416

10. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
The price is CA $343
CA $408 total
includes taxes & fees
Nov 30 - Dec 1
2BR Oceanfront Suite w/ Beach & Marina Access

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

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (258 reviews)
"Great place, big pool and great location to restaurants and nearby activities"
United States
Anthony R.
The price is CA $286
CA $604 total
includes taxes & fees
Nov 20 - Nov 21
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

12. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
The price is CA $267
CA $497 total
includes taxes & fees
Nov 11 - Nov 12
Ocean Pointe Ocean View w/heated pool beach marina

13. Blue Haven | Nature View 2BR | Ocean Pointe 1315

Blue Haven | Nature View 2BR | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
The price is CA $243
CA $616 total
includes taxes & fees
Nov 10 - Nov 11
Blue Haven | Nature View 2BR | Ocean Pointe 1315

14. Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
Tavernier
9.4 out of 10, Exceptional, (3 reviews)
"Very clean. The view was amazing. Very comfortable beds. We are definitely coming back to this condo! "
United States
Jason U.
The price is CA $243
CA $614 total
includes taxes & fees
Nov 10 - Nov 11
Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $184
CA $520 total
includes taxes & fees
Nov 19 - Nov 20
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

16. Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (103 reviews)
"Great visit!"
United States
Leigh D. H.
The price is CA $267
CA $511 total
includes taxes & fees
Nov 12 - Nov 13
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

17. Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun

Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
The price is CA $319
CA $558 total
includes taxes & fees
Nov 10 - Nov 11
Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun

18. Lazy Daze | Double King Suite | Ocean Pointe 2310

Lazy Daze | Double King Suite | Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
The price is CA $267
CA $644 total
includes taxes & fees
Nov 17 - Nov 18
Lazy Daze | Double King Suite | Ocean Pointe 2310

19. Starfish Seas | Ocean View | Ocean Pointe 1302

Starfish Seas | Ocean View | Ocean Pointe 1302
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is CA $267
CA $644 total
includes taxes & fees
Nov 18 - Nov 19
Starfish Seas | Ocean View | Ocean Pointe 1302

20. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Great stay"
United States
Blain R.
The price is CA $234
CA $606 total
includes taxes & fees
Nov 16 - Nov 17
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windley Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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