Title: Cow Key Vacation Home Rentals from CA $627: Search Top Private Vacation Homes for Rent | Expedia.ca

[Cow Key Travel Guide](https://expedia.ca/Cow-Key.dx180163)[Hotels in Cow Key](https://expedia.ca/Cow-Key-Hotels.d180163.Travel-Guide-Hotels)[Vacation Rentals in Cow Key](https://expedia.ca/Cow-Key-Vacation-Rentals.d180163.Travel-Guide-VacationRentals)[Cow Key Car Rentals](https://expedia.ca/Car-Rentals-In-Cow-Key.d180163.Car-Rental-Guide)[Cow Key Vacation Packages](https://expedia.ca/Cow-Key.d180163.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cow Key vacation homes

![Exterior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d56a9a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![LED TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/787fb31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information)

Cudjoe Key

9.4/10

Exceptional

(102 reviews)

"Great location. "

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

Davian k.

CA $231

CA $627 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information)

![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/2a1c9fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/10b16cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/eafa7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/5ac36685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Fairhaven House at Solaire Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information)

Raccoon Key

CA $3,683

CA $5,469 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/08f26cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/5fa1ecc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information)

Cudjoe Key

CA $342

CA $918 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/a01f4162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e29d300c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/w2500h1666x0y1-8de3e595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/67b94030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information)

Cudjoe Key

9.2/10

Wonderful

(7 reviews)

"Close to Key West. Would stay there again!!"

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

elisa b.

CA $272

CA $830 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/61fc156d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/092ca3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0ce6f815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/cf94feca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shellstone House at Solaire Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information)

Raccoon Key

10/10

Exceptional

(2 reviews)

"Beautiful home with great outdoor space and we loved the pool and private dock"

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

Sharon L.

CA $2,180

CA $4,147 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/6e3c9448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h819x1y0-b2147544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1284h2247x0y0-fe8bc1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/86d1247e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information)

Cudjoe Key

7.6/10

Good

(13 reviews)

"Good experience. The property is well place and the Venture is really nice and quiet."

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

Primeau J.

CA $338

CA $706 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/4c3dc49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/a935335c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/393a2acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/20d90f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(1 review)

"Very clean! Good location. "

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

January M.

CA $466

CA $1,075 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/7fa52371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/60a3d49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/463cda70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/f6d4e696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax by Florida Keys Beaches, just a 7-min drive away

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information)

Cudjoe Key

9.8/10

Exceptional

(201 reviews)

"Will definitely stay here again "

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

Jeannine R.

CA $375

CA $897 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/2f0f66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/29ebdd14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/b5a934e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/a7e2aa66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hemingway - Beach Houses Key West

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.Hotel-Information)

Upper Sugarloaf Key

9.6/10

Exceptional

(8 reviews)

"Perfect location way off the path if you like seclusion."

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

Jonathan L.

CA $1,090

CA $2,071 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/22e311d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/65dacfe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/d8e3a0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/b4b21153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mirador House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Mirador-House-At-Lunara-Bay.h74132647.Hotel-Information)

Raccoon Key

9.6/10

Exceptional

(34 reviews)

"Fantastic property! Fantastic hosts! Fantastic pool! Would highly recommend staying here, we had an amazing time. "

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

Claudia S.

CA $1,360

CA $2,910 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Key-West-Hotels-Mirador-House-At-Lunara-Bay.h74132647.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/46f398f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/53e705db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/07101baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/5cc75497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Altair House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(12 reviews)

"Great house. Large space, everything you need is there. "

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

CRIMSON A.

CA $1,429

CA $3,109 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/b85cd3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a00c4a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/93c22143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/ee43d350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Luxury Home - Tidelands House

[](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

Raccoon Key

CA $2,490

CA $4,127 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/5c412777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9c855c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/268b6c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9b31843e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Dreamside House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information)

Raccoon Key

9.4/10

Exceptional

(3 reviews)

"Size was perfect. Beautiful back yard. Great that there was a bathroom for every bedroom. "

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

Kristin E.

CA $1,776

CA $3,637 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/5cf2b74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/2661692e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/4a8c25f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/862d13b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 105 - Newly renovated house Oceanside and Pool

[](https://www.expedia.ca/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.Hotel-Information)

Cudjoe Key

CA $494

CA $1,127 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/37ba1c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/00d34243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/4a876812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/a6150bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spanish Queen @Venture Out, Cudjoe Key

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information)

Cudjoe Key

9.4/10

Exceptional

(19 reviews)

"This is our third time staying here. It is a great property and works perfectly for a three-person family."

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

Kimberly G.

CA $477

CA $934 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/3e905f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/23ac2d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/2c998f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/1e949ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Reel Island Retreat #273 at Venture Out in the Florida Keys

[](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information)

Cudjoe Key

9.6/10

Exceptional

(7 reviews)

"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "

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

Lindsay C.

CA $430

CA $1,029 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/beabdb4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/w2500h1666x0y1-6df08e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/222af626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/27011986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

[](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.Hotel-Information)

Cudjoe Key

9.2/10

Wonderful

(29 reviews)

"Close to Key West and lots of great boating"

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

Simon S.

CA $466

CA $1,075 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/080e8cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information)

Cudjoe Key

9.8/10

Exceptional

(82 reviews)

"The place is clean and convenient for anyone wanting to spend time on the water in the keys"

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

Ubaldo G.

CA $531

CA $1,010 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/f12238b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/02e9b6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/466c62c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/a6d00a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suncoast House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.Hotel-Information)

Raccoon Key

9.6/10

Exceptional

(42 reviews)

"Beautiful House, super clean, perfect location "

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

carlos s.

CA $1,360

CA $2,910 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/d88aeee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/3c832205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/14d16ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/34b098b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Catchlight House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-Catchlight-House-With-Private-Pool.h107978707.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(6 reviews)

"Awesome place definitely recommend if going to key west "

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

Brandon M.

CA $1,429

CA $3,109 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-Catchlight-House-With-Private-Pool.h107978707.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=2026-02-19&endDate=2026-02-20&regionId=180163&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

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Cottages

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Private vacation homes

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Condos

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Cow+Key%2C+Florida%2C+United+States+of+America&regionId=180163&latLong=24.560702%2C-81.741201&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Cow+Key%2C+Florida%2C+United+States+of+America&regionId=180163&latLong=24.560702%2C-81.741201&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=HOUSE_BOAT)

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## Top Cow Key Hotel Reviews

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg)

### Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Everything the room washer dryer the staff and the view "

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information)

![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg)

### Parrot Key Hotel & Villas

10/10 Excellent

"This is my second time staying at the Parrot Key. Love the hotel. Beautiful property & rooms, plus the staff is always accommodating & pleasant. The hotels location is also great, just a five to eight minute drive to Duval. I would highly recommend staying there. "

[](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information)

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg)

### Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"It was a great experience and the room was amazing would definitely come back here on our next vacation "

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information)

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg)

### Beachside Resort & Residences

10/10 Excellent

"The staff was great. The room was good."

[](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information)

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg)

### Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent

"The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. We would definitely stay there again. "

[](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg)

### DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Flawless."

[](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information)

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg)

### Blue Flamingo Resort Key West

10/10 Excellent

"Great property! We had a junior suite and it was extremely spacious. The staff was very nice and the free shuttle to Duval St was a great perk. My only complaint was that nobody, but nobody told you to make a reservation for the free shuttle. I talked to multiple people at the front desk, concierge and on the phone… not one word about making a reservation. We saw countless people deal with that same situation. Kinda frustrating getting told you can’t get on the shuttle when you’ve been waiting for up to an hour. "

[](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information)

![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg)

### Margaritaville Beach House Key West

10/10 Excellent

"This was my favorite hotel during out recent trip to the Keys. I really enjoyed all the little perks they offer like poolside smoothies, cookies and the shuttle. The pool area is very relaxing and fun to hang out at. The rooms were nice including comfortable beds and clean bathrooms. The staff was excellent. I also enjoyed that this hotel is away from all the busy areas on the island and there is a beach across the street."

[](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information)

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg)

### Ibis Bay Beach Resort

10/10 Excellent

"Everything was fantastic"

[](https://expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information)

## Find out more about Cow Key

## Cow Key Vacation Homes information

| Number of reviews | 541                 |
| ----------------- | ------------------- |
| Accommodation     | 1323 Vacation Homes |
| Lowest Price      | CA $627             |
| Highest Price     | CA $5,469           |

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- [Stock Island Vacations ](https://www.expedia.ca/Stock-Island.d180166.Destination-Travel-Guides)
- [Visit Stock Island ](https://www.expedia.ca/Stock-Island.dx180166)

- [Ada Rental Cars in Stock Island ](https://www.expedia.ca/ADA-Car-Rentals-In-Stock-Island.d180166-c1109.Car-Rental-Guide-Suppliers)
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- [Things to do in Stock Island ](https://www.expedia.ca/Things-To-Do-In-Stock-Island.d180166.Travel-Guide-Activities)

- [Book Vacation Homes in Cow Key on Expedia.com ](https://www.expedia.com/Cow-Key-Private-Vacation-Homes.d180163-aaPrivateVacationHomes.Travel-Guide-Accommodation)