Title: Windley Key Vacation Rentals from CA $312: Short-Term Rentals for 2026 | Expedia.ca

[Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)

![Theater of the Sea](https://images.trvl-media.com/place/6069249/5a39f3a2-0de6-49e9-a8f9-b4e8e17b70ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Windley Key Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-25&endDate=2025-12-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-26&endDate=2025-12-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windley Key vacation rentals

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treasure Harbor

[](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

Islamorada

9.0/10

Wonderful

(117)

"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary

[](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Cottage | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/7a0bffa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breezy Palms Resort

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

Matecumbe

8.8/10

Excellent

(592)

"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Terry

CA $215

CA $312 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/5be55ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Islands of Islamorada

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

Matecumbe

9.8/10

Exceptional

(70)

"Great for family vacation with kids. love it"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dixania

CA $833

CA $1,012 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/7f2e2269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/0514aa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Conch Key One-bedroom Cottage | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/3c8c13d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Key Largo One-bedroom Cottage](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/29275608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Bay Resort

[](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information)

Tavernier

10/10

Exceptional

(141)

"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

[](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information)

![Fishing](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/b43053cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Living area](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/1ac6888f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment | Private kitchen](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/8d608263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Terrace/patio](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/923a2492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kings Kamp

[](https://www.expedia.ca/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

Key Largo

8.8/10

Excellent

(23)

"Kings Kamp was a charming stay. The owners were friendly and made the stay easy"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erica

CA $376

CA $423 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dc4f4949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/c244835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/f15964b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Floating Bungalow by Stay Ombi

[](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

Key Largo

CA $1,722

CA $1,937 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/123000000/122340000/122335800/122335752/3aa63d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/123000000/122340000/122335800/122335752/3da57867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/123000000/122340000/122335800/122335752/w1535h1024x1y1-e8de4202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122340000/122335800/122335752/e8f34b06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachfront Retreat w Pool, Boat Ramp & Dock Rental

[](https://www.expedia.ca/Key-Largo-Hotels-Beachfront-Retreat-W-Pool.h122335752.Hotel-Information)

Key Largo

10/10

Exceptional

(2)

"Set up of RV was very nice. Great location and amenities at the campground."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cynthia C.

CA $163

CA $446 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Beachfront-Retreat-W-Pool.h122335752.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/822e7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/b5e8e966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/28450ffb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/c064b61a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity In The Sun Condo Fabulous Ocean View

[](https://www.expedia.ca/Tavernier-Hotels-Serenity-In-The-Sun-Condo-Fabulous-Ocean-View.h53645406.Hotel-Information)

Tavernier

10/10

Exceptional

(108)

"Fantastic place to stay! Very clean and great hosts. Will stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Les

CA $308

CA $661 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Serenity-In-The-Sun-Condo-Fabulous-Ocean-View.h53645406.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/72daed41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/16ce2e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/e7e5ee70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/52ff82ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lazy Daze Double King Suite Ocean Pointe 2310

[](https://www.expedia.ca/Tavernier-Hotels-Lazy-Daze-Double-King-Suite-Ocean-Pointe-2310.h78256364.Hotel-Information)

Tavernier

9.8/10

Exceptional

(26)

"Everything was exceptionally nice. Would definitely book again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharon

CA $267

CA $659 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Lazy-Daze-Double-King-Suite-Ocean-Pointe-2310.h78256364.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/895e45f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/737e91ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/1379ede6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/012c4b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information)

Tavernier

9.8/10

Exceptional

(210)

"Heidi has a little bit of paradise on her houseboat! You must plan on staying!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Toni M.

CA $410

CA $685 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/75000000/74060000/74058200/74058185/87fe04a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74060000/74058200/74058185/04bfb26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74060000/74058200/74058185/d4b08acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74060000/74058200/74058185/665ac8a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise in Key Largo, FL

[](https://www.expedia.ca/Key-Largo-Hotels-Paradise-In-Key-Largo.h74058185.Hotel-Information)

Key Largo

9.6/10

Exceptional

(61)

"Beautiful property. We uh, I very much enjoyed our stay highly recommend we will stay here again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

George D.

CA $185

CA $425 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Paradise-In-Key-Largo.h74058185.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/647c5456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/w1078h802x1y198-a3a83b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/4400c7a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/442e9a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW ! Lagoon-front townhouse with Marina in Key Largo

[](https://www.expedia.ca/Key-Largo-Hotels-Marvelous-2-Bedroom-House-With-AC-In-Key-Largo.h120624610.Hotel-Information)

Key Largo

10/10

Exceptional

(46)

"Good location. Lagoon and pool right outside door. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Debra C.

CA $457

CA $905 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Marvelous-2-Bedroom-House-With-AC-In-Key-Largo.h120624610.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/w1052h665x0y34-299237c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/0ae91338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/b09b34f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/66d12570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal comfort in Ocean Pointe Suites. 

[](https://www.expedia.ca/Tavernier-Hotels-Warm-Winter-Escape-In-Sunny-Florida-Keys-With-Oceanfront-Private-BeachMarina.h42281802.Hotel-Information)

Tavernier

10/10

Exceptional

(33)

"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert F.

CA $369

CA $937 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Warm-Winter-Escape-In-Sunny-Florida-Keys-With-Oceanfront-Private-BeachMarina.h42281802.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/109000000/108880000/108879000/108878919/c60eb0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108880000/108879000/108878919/403f7716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108880000/108879000/108878919/ea9a3e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/109000000/108880000/108879000/108878919/b42e3366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

[](https://www.expedia.ca/Tavernier-Hotels-Ocean-View-Gem-Ocean-Pointe-3406.h108878919.Hotel-Information)

Tavernier

10/10

Exceptional

(3)

"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin W.

CA $321

CA $726 total

includes taxes & fees

Jan 21 - Jan 22, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Ocean-View-Gem-Ocean-Pointe-3406.h108878919.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256353/cdd7becc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256353/8660af17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256353/e5d544cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256353/6b3fca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern and Coastal Ocean Pointe 2307

[](https://www.expedia.ca/Tavernier-Hotels-Modern-Coastal-Renovation.h78256353.Hotel-Information)

Tavernier

10/10

Exceptional

(122)

"We enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Halley R.

CA $207

CA $569 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Modern-Coastal-Renovation.h78256353.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/107000000/106880000/106875800/106875784/edd58440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106880000/106875800/106875784/1ea6a354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106880000/106875800/106875784/c3d94e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/107000000/106880000/106875800/106875784/b09b059b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Condo w/ Ocean View, Pool & Tropical Setting

[](https://www.expedia.ca/Tavernier-Hotels-2BR-Condo-W-Ocean-View.h106875784.Hotel-Information)

Tavernier

9.6/10

Exceptional

(4)

" centrally located for keys travel"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gary

CA $399

CA $736 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Tavernier-Hotels-2BR-Condo-W-Ocean-View.h106875784.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/112000000/111090000/111087200/111087158/da77210d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111090000/111087200/111087158/18ef3644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111090000/111087200/111087158/8f562d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/112000000/111090000/111087200/111087158/1ad79dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Happy in the Keys Tiny Home-in Key Largo. 

[](https://www.expedia.ca/Key-Largo-Hotels-Charming-3-Bedroom-Tiny-Home-In-Peaceful-Key-Largo-Retreat.h111087158.Hotel-Information)

Key Largo

10/10

Exceptional

(10)

"It was a lovely place, very clean and comfortable. Will be definitely be coming back. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carol

CA $226

CA $551 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-Charming-3-Bedroom-Tiny-Home-In-Peaceful-Key-Largo-Retreat.h111087158.Hotel-Information)

![2 bedrooms, in-room safe, desk, bed sheets](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w903h683x61y0-6a8ad40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w903h683x60y0-ed597f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-23f3304c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-10596317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Sanctuary Islamorada

[](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.Hotel-Information)

Tavernier

9.8/10

Exceptional

(12)

"It exceeded our expectations, and we are so glad we found this location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenn H.

CA $363

CA $572 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383398/bfc84dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383398/cd1af683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383398/72f54992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383398/c449b326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aqua Vista Ocean Pointe 3307

[](https://www.expedia.ca/Tavernier-Hotels-Aqua-Vista-Ocean-Pointe-3307.h106383398.Hotel-Information)

Tavernier

10/10

Exceptional

(1)

"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

CA $286

CA $681 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Tavernier-Hotels-Aqua-Vista-Ocean-Pointe-3307.h106383398.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119460000/119451000/119450905/40a73590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119460000/119451000/119450905/aa3730b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119460000/119451000/119450905/f07863a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119460000/119451000/119450905/16c8fbe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Coral House - Bayside Retreat for 6-8 guests

[](https://www.expedia.ca/Key-Largo-Hotels-The-Coral-House-Bayside-Retreat-For-6-10-Guests.h119450905.Hotel-Information)

Key Largo

7.8/10

Good

(7)

"Great location with private beach loved it "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bobby A.

CA $1,366

CA $1,551 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Key-Largo-Hotels-The-Coral-House-Bayside-Retreat-For-6-10-Guests.h119450905.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09&regionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=HOUSE_BOAT)

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## Top Windley Key Hotel Reviews

![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg)

### Bayside Inn Key Largo

10/10 Excellent

"Yes"

[](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg)

### Lime Tree Bay Resort

10/10 Excellent

"This place is the best kept secret "

[](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg)

### Fisher Inn Resort & Marina

10/10 Excellent

"We enjoyed are stay at Fisher Inn, room was clean and updated. The paddle board use was a nice perk! "

[](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special! "

[](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Always a great experience every time we go to key largo we stay there "

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg)

### Cheeca Lodge & Spa

10/10 Excellent

"Fabulous waterfront, activities, and dining as well as the staff. "

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg)

### Creekside Inn

10/10 Excellent

"Goo"

[](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information)

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"The breakfasts are great "

[](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg)

### Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"Very good "

[](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information)

## 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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- [Vacation Homes in Windley Key ](https://expedia.ca/Windley-Key-Private-Vacation-Homes.d553248635976197663-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Car rentals in International Drive District](https://expedia.ca/Car-Rentals-In-International-Drive-District.d6034244.Car-Rental-Guide)

Activities

- [Things to do in Boca Chica Key](https://expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)
- [Things to do in Golden](https://expedia.ca/Things-To-Do-In-Golden.d6058316.Travel-Guide-Activities)

General

- [Visit Union Square](https://expedia.ca/San-Francisco-Union-Square.dx800129)
- [Visit Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park.dx6160046)

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