Title: Windley Key Vacation Rentals from CA $286: 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)

![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Windley Key Vacation Rentals

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-04-24&endDate=2026-04-26&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)

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

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.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

(121)

"Great spot! Will be back someday hopefully. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Diane

CA $209

CA $428 total

includes taxes & fees

Jan 5 - Jan 6

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

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/a7f8b8c7.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 $1,555

CA $1,749 total

includes taxes & fees

Jan 29 - Jan 30

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

![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)

![Deluxe Cottage](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.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

(602)

"Property was nice and easy to navigate, ocean view room was extra nice to have!"

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

Lisa

CA $191

CA $286 total

includes taxes & fees

Jan 12 - Jan 13

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

![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)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/123000000/122340000/122335800/122335752/w1536h1023x0y1-1c9f7942.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

(3)

"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 $155

CA $440 total

includes taxes & fees

Jan 7 - Jan 8

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

![Property grounds](https://images.trvl-media.com/lodging/100000000/99380000/99379100/99379050/w720h480x0y0-addd0c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/100000000/99380000/99379100/99379050/944bc2b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99380000/99379100/99379050/f784540b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99380000/99379100/99379050/51e2fc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RV by the Sea - Glamping in the Keys - Sleeps 6

[](https://www.expedia.ca/Key-Largo-Hotels-RV-By-The-Sea-Glamping-In-The-Keys-Sleeps-6.h99379050.Hotel-Information)

Key Largo

8.8/10

Excellent

(19)

"Fun accommodation in Key Largo. Clean, good size, nice pool."

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

James C.

CA $97

CA $371 total

includes taxes & fees

Jan 6 - Jan 7

[](https://www.expedia.ca/Key-Largo-Hotels-RV-By-The-Sea-Glamping-In-The-Keys-Sleeps-6.h99379050.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/78000000/77940000/77937700/77937661/076d9453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/78000000/77940000/77937700/77937661/da432f7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77940000/77937700/77937661/93009341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77940000/77937700/77937661/93688c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise in Key Largo Florida 2

[](https://www.expedia.ca/Key-Largo-Hotels-Paradise-In-Key-Largo-Florida.h77937661.Hotel-Information)

Key Largo

9.8/10

Exceptional

(41)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steve V.

CA $173

CA $424 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Key-Largo-Hotels-Paradise-In-Key-Largo-Florida.h77937661.Hotel-Information)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/102000000/101240000/101232100/101232074/d41b15fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101240000/101232100/101232074/e27d0da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/102000000/101240000/101232100/101232074/dea19358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101240000/101232100/101232074/0864a30f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy place in Calusa Key Largo

[](https://www.expedia.ca/Key-Largo-Hotels-Cozy-Place-In-Calusa-Key-Largo.h101232074.Hotel-Information)

Key Largo

9.4/10

Exceptional

(12)

"Perfect weekend getaway location."

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

Tex H.

CA $158

CA $453 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Key-Largo-Hotels-Cozy-Place-In-Calusa-Key-Largo.h101232074.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)

![Private beach, sun loungers](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/96315701.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)

![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)

### Kings Kamp

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

Key Largo

8.6/10

Excellent

(25)

"Clean room, Beautiful view of the sea from the room window."

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

Serhiy

CA $377

CA $424 total

includes taxes & fees

Jan 4 - Jan 5

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

![Pool](https://images.trvl-media.com/lodging/64000000/63120000/63112600/63112538/82e6e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/64000000/63120000/63112600/63112538/0464ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63120000/63112600/63112538/276a3898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/64000000/63120000/63112600/63112538/94f309cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Ocean view condo

[](https://www.expedia.ca/Tavernier-Hotels-Amazing-Ocean-View-Condo.h63112538.Hotel-Information)

Tavernier

9.6/10

Exceptional

(42)

"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"

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

Natalie M.

CA $225

CA $521 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Tavernier-Hotels-Amazing-Ocean-View-Condo.h63112538.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/94241dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/078f0b06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/95c54ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/b3fdbd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Home in Key Largo

[](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.Hotel-Information)

Key Largo

9.8/10

Exceptional

(29)

"It was clean and a very nice place to stay. Plenty of room and awesome amenities."

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

Eric M.

CA $221

CA $625 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.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)

![Marina](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-10596317.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)

### Island Sanctuary Islamorada

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

Tavernier

9.8/10

Exceptional

(13)

"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 $364

CA $547 total

includes taxes & fees

Jan 3 - Jan 4

[](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.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 $235

CA $600 total

includes taxes & fees

Jan 19 - Jan 20

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

![Property grounds](https://images.trvl-media.com/lodging/91000000/90530000/90524700/90524666/d754d352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/91000000/90530000/90524700/90524666/7d3e3e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90530000/90524700/90524666/83b3602f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/91000000/90530000/90524700/90524666/2f4fe73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Florida Keys Getaway - Slps 4 - Ocean View

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Getaway-Slps-4-Ocean-View.h90524666.Hotel-Information)

Tavernier

9.6/10

Exceptional

(19)

"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "

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

Michele G.

CA $180

CA $500 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Getaway-Slps-4-Ocean-View.h90524666.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)

![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)

![Marina](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/28450ffb.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 $295

CA $646 total

includes taxes & fees

Jan 6 - Jan 7

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

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/79000000/78540000/78534000/78533920/aadb7e70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78540000/78534000/78533920/e15b65b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78540000/78534000/78533920/1f7903f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78540000/78534000/78533920/51397bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Where the sea, sun, and sand are just outside your door!

[](https://www.expedia.ca/Key-Largo-Hotels-Welcome-To-Paradise-II.h78533920.Hotel-Information)

Key Largo

9.6/10

Exceptional

(31)

"Everything is as described. We brought our boat and used the marina. Our trailer fit on the property’s as well. "

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

Jane O.

CA $303

CA $566 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-Largo-Hotels-Welcome-To-Paradise-II.h78533920.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/2e6dec1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/w1535h1024x1y1-14607650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/46854630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/97916ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Key-Largo-Hotels-New-Tiny-Home-Paddle-Boards.h90174063.Hotel-Information)

Key Largo

9.6/10

Exceptional

(85)

"Very quiet and cozy "

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

Stephanie T.

CA $206

CA $550 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Key-Largo-Hotels-New-Tiny-Home-Paddle-Boards.h90174063.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)

![Exterior](https://images.trvl-media.com/lodging/112000000/111090000/111087200/111087158/56f86889.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)

### 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 $198

CA $516 total

includes taxes & fees

Jan 10 - Jan 11

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

![Outdoor dining](https://images.trvl-media.com/lodging/40000000/40000000/39990300/39990272/10270958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/40000000/40000000/39990300/39990272/5af3af70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/40000000/39990300/39990272/fea4e178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/40000000/39990300/39990272/39ba9797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Key-Largo-Hotels-2-BR2-BA-Oasis-W-Kayak.h39990272.Hotel-Information)

Key Largo

8.6/10

Excellent

(88)

"It was very clean. Pet friendly. Everybody at the campground is wonderful."

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

Tammie F.

CA $187

CA $478 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-Largo-Hotels-2-BR2-BA-Oasis-W-Kayak.h39990272.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/88000000/87830000/87824100/87824083/7edc0ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/88000000/87830000/87824100/87824083/b7b8bab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87830000/87824100/87824083/cd09e26f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/88000000/87830000/87824100/87824083/a48ed721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Haven Key Largo | Ocean Pointe 1315

[](https://www.expedia.ca/Tavernier-Hotels-Blue-Haven-Key-Largo-Ocean-Pointe-1315.h87824083.Hotel-Information)

Tavernier

9.6/10

Exceptional

(15)

"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"

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

Philippa

CA $218

CA $583 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Tavernier-Hotels-Blue-Haven-Key-Largo-Ocean-Pointe-1315.h87824083.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100160000/100150100/100150070/58cd76fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/101000000/100160000/100150100/100150070/5a8ec4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/101000000/100160000/100150100/100150070/4cdbd36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100160000/100150100/100150070/2dd3be06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Chic Ocean Pointe 3214

[](https://www.expedia.ca/Tavernier-Hotels-Boho-Chic-Ocean-Pointe-3214.h100150070.Hotel-Information)

Tavernier

10/10

Exceptional

(12)

"It was clean, well organized and communication was great. Had a good time."

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

Shirl

CA $257

CA $640 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Tavernier-Hotels-Boho-Chic-Ocean-Pointe-3214.h100150070.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=2026-01-16&endDate=2026-01-17&regionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)

## Top Windley Key Hotel Reviews

![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg)

### Drop Anchor

10/10 Excellent

"The staff was personable, great location, having the bicycles and kayaks were a great touch"

[](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information)

![Holiday Inn Key Largo by IHG](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg)

### Holiday Inn Key Largo by IHG

10/10 Excellent

"Comfortable and convenient. Enjoyed the shade of the tiki huts."

[](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information)

![Playa Largo Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg)

### Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"Courteous staff, clean, many extra like hot chocolate bar, s’mores station and coffee station. Nice stay!"

[](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information)

![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg)

### Reefhouse Resort & Marina

10/10 Excellent

"Great staff and facility"

[](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information)

![Rock Reef Resort](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg)

### Rock Reef Resort

10/10 Excellent

"Cute hotel a great location for our trip through the Keys.. the room was clean and comfortable and the staff was friendly and helpful.. "

[](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information)

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

### Chesapeake Beach Resort

10/10 Excellent

"Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return."

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

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

### Bayside Inn Key Largo

10/10 Excellent

"Room was clean and the staff was super helpful and friendly. Highly recommend! "

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

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"Great place, staff was very friendly, I would highly recommend "

[](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.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

"everything was wonderful! the room, the staff, the view! it was perfect!"

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

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Windley Key

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Windley Key ](https://expedia.ca/Windley-Key-Private-Vacation-Homes.d553248635976197663-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Windley Key ](https://expedia.ca/Windley-Key-Condos.d553248635976197663-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Windley Key ](https://expedia.ca/Windley-Key-Apartments.d553248635976197663-aaApartments.Travel-Guide-Accommodation)
- [Villas in Windley Key ](https://expedia.ca/Windley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)
- [Cottages in Windley Key ](https://expedia.ca/Windley-Key-Cottages.d553248635976197663-aaCottages.Travel-Guide-Accommodation)
- [Houseboats in Windley Key ](https://expedia.ca/Windley-Key-Houseboats.d553248635976197663-aaHouseboats.Travel-Guide-Accommodation)
- [Aparthotels in Windley Key ](https://expedia.ca/Windley-Key-Apart-Hotels.d553248635976197663-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Windley Key ](https://expedia.ca/Windley-Key-RV-Parks.d553248635976197663-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Windley Key ](https://expedia.ca/Windley-Key-Resort-Hotels.d553248635976197663-aaResortHotels.Travel-Guide-Accommodation)
- [Motels in Windley Key ](https://expedia.ca/Windley-Key-Motels.d553248635976197663-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Windley Key ](https://expedia.ca/Windley-Key-Guest-Houses.d553248635976197663-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Windley Key ](https://expedia.ca/Windley-Key-Cabins.d553248635976197663-aaCabins.Travel-Guide-Accommodation)
- [Lodges in Windley Key ](https://expedia.ca/Windley-Key-Lodges.d553248635976197663-aaLodges.Travel-Guide-Accommodation)
- [Condo Resorts in Windley Key ](https://expedia.ca/Windley-Key-Condominium-Resort.d553248635976197663-aaCondominiumResort.Travel-Guide-Accommodation)

### Expedia's Latest Trends

Hotels

- [Hotels in Amelia Island](https://expedia.ca/Amelia-Island-Hotels.d10814.Travel-Guide-Hotels)
- [Cheap Hotels in International Drive District](https://expedia.ca/International-Drive-District-Orlando-Hotels-Cheap-Hotels.0-n6034244-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [International Drive District hotels](https://expedia.ca/International-Drive-District-Orlando-Hotels.0-n6034244-0.Travel-Guide-Filter-Hotels)
- [Hotels in Prince Edward](https://expedia.ca/Prince-Edward-Hotels.d553248635924757362.Travel-Guide-Hotels)
- [Sherwood Inn](https://expedia.ca/Huntsville-Hotels-Sherwood-Inn.h699045.Hotel-Information)
- [Sleep Inn & Suites Buffalo Airport](https://expedia.ca/Buffalo-Hotels-Sleep-Inn-Suites-Buffalo-Airport.h85007.Hotel-Information)
- [The Scott Resort & Spa ](https://expedia.ca/Phoenix-Hotels-The-Scott-Resort-Spa.h2557.Hotel-Information)
- [Park Hyatt New York](https://expedia.ca/New-York-Hotels-Park-Hyatt-New-York.h7650971.Hotel-Information)
- [Oakwood Premier Tokyo](https://expedia.ca/Tokyo-Hotels-Oakwood-Premier-Tokyo.h13061201.Hotel-Information)
- [Hotels with Free Airport Shuttle in International Drive District](https://expedia.ca/International-Drive-District-Orlando-Hotels-Hotels-With-Free-Airport-Shuttle.0-n6034244-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Bisha, a Luxury Collection Hotel Toronto](https://expedia.ca/Toronto-Hotels-Bisha-Hotel-Toronto.h18669075.Hotel-Information)

Flights

- [Cheap Flights from Edmonton (YEG) to Orlando (MCO)](https://expedia.ca/lp/flights/yeg/mco/edmonton-to-orlando)
- [Cheap Flights from Montreal](https://expedia.ca/lp/flights/178288/flights-from-montreal)
- [Cheap Flights from Edmonton (YEG) to Zürich (ZRH)](https://expedia.ca/lp/flights/yeg/zrh/edmonton-to-zurich)
- [Cheap Flights to Amelia Island](https://expedia.ca/Cheap-Flights-To-Amelia-Island.d10814.Travel-Guide-Flights)
- [Flights to India](https://expedia.ca/Destinations-In-India.d80.Flight-Destinations)
- [Cheap Flights from Toronto (YYZ) to Milan (MXP)](https://expedia.ca/lp/flights/yyz/mxp/toronto-to-milan)
- [Cheap Flights from Toronto (YYZ) to Split (SPU)](https://expedia.ca/lp/flights/yyz/spu/toronto-to-split)
- [WestJet Toronto (YYZ) to Fort Myers (RSW) flights](https://expedia.ca/lp/flight-routes/westjet-from-pearson-intl-to-southwest-florida-intl/ws/yyz/rsw)
- [Cheap Flights from Belize City (BZE) to San Pedro (SPR)](https://expedia.ca/lp/flights/bze/spr/belize-city-to-san-pedro)
- [Cheap Flights from Toronto (YYZ) to Tokyo (TYO)](https://expedia.ca/lp/flights/yyz/tyo/toronto-to-tokyo)

Cars

- [Car rental Kailua-Kona Airport (KOA)](https://expedia.ca/Car-Rentals-In-Kona-Intl.d4280139.Car-Rental-Guide)
- [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)

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app