Title: Cow Key Vacation Rentals from CA $434: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-07-17&endDate=2026-07-19&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 rentals

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/1387427b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/94d6428a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/3bedcb76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/a01f6053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(80 reviews)

"It was a nice location. 30” from Key West. "

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

Linda N.

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/87c78511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/f7550de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/99362c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/05b75118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grand Marina Suite by Brightwild Waterfront

[](https://www.expedia.ca/Key-West-Hotels-Grand-Marina-Suite-By-Brightwild-Waterfront.h109003026.Hotel-Information)

Stock Island

10/10

Exceptional

(3 reviews)

"Nice place "

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

Pawel

CA $872

CA $1,305 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Key-West-Hotels-Grand-Marina-Suite-By-Brightwild-Waterfront.h109003026.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fa9fff97.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/34000000/33570000/33566300/33566283/fcb4c32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage with swimming pool and dockage, just minutes to Key West!

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(167 reviews)

"Location was perfect. Oceanfront dock had beautiful sunsets. Oceanfront pool lovely and warm with incredible view. Very friendly vibe and relaxed atmosphere. "

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

Jennifer

CA $247

CA $442 total

includes taxes & fees

Mar 27 - Mar 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.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/45000000/44560000/44556700/44556643/080e8cfe.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)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/1020b125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SAVE BIG $$$ APRIL! 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

(86 reviews)

"The rental was super clean and beautiful."

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

christopher v.

CA $342

CA $773 total

includes taxes & fees

Apr 3 - Apr 4

[](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/95000000/94620000/94616500/94616487/d62d627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/2ea056a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/bf68a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/a03560e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private and Exclusive Florida Keys Getaway

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information)

Upper Sugarloaf Key

10/10

Exceptional

(14 reviews)

"Beautiful! Pool was amazing!"

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

Jennifer B.

CA $1,502

CA $2,573 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/78df4af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/6a3c7406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/7ec8a365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Home

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(178 reviews)

"Great location if you bring a boat. Secure location. Venture Out is a nice community. "

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

Georgiana V.

CA $309

CA $624 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.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)

![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/a6150bdb.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)

![Sport court](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/25a85f73.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

(20 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 $480

CA $939 total

includes taxes & fees

Apr 13 - Apr 14

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

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/4d522535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/ad59ca22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/80422f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/02900870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Capmar House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(29 reviews)

"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"

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

Anonymous traveller

CA $1,096

CA $2,346 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/dc4f2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cudjoe Cottages, swimming pool, just 20 miles from Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(154 reviews)

"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "

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

Peggy H.

CA $480

CA $958 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1435x0y0-13878f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1148x0y0-e3e5de04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/ac960d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1916h1147x0y0-2466c03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Direct-Oceanfront-Atlantic-Side-Dockage-Pool-And-20-Miles-From-Key-West.h33483790.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(163 reviews)

"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "

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

Phillip

CA $432

CA $897 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Summerland-Key-Hotels-Direct-Oceanfront-Atlantic-Side-Dockage-Pool-And-20-Miles-From-Key-West.h33483790.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/c6ea30d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/c4067d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w905h683x60y0-701bb32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/6b75217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise found

[](https://www.expedia.ca/Key-West-Hotels-Paradise-Found.h79683240.Hotel-Information)

Stock Island

9.8/10

Exceptional

(34 reviews)

"Great house and location. We have found our rental for our yearly stay in Key West. "

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

Elizabeth F.

CA $548

CA $1,016 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Key-West-Hotels-Paradise-Found.h79683240.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/c247b637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/e8ea6ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/2db43d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/d5b29171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort View 1BR Suite With Direct Pool Access

[](https://www.expedia.ca/Key-West-Hotels-Resort-View-1BR-Suite-With-Direct-Pool-Access.h109003134.Hotel-Information)

Key West

CA $701

CA $903 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Key-West-Hotels-Resort-View-1BR-Suite-With-Direct-Pool-Access.h109003134.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/115000000/114480000/114470400/114470329/300cc8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114480000/114470400/114470329/2094b3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114480000/114470400/114470329/883bdc70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114480000/114470400/114470329/1d8480a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

[](https://www.expedia.ca/Summerland-Key-Hotels-Keys-To-Paradise-95-56-Dock-Ocean-Views.h114470329.Hotel-Information)

Cudjoe Key

9.8/10

Exceptional

(145 reviews)

"Super relaxing! Great location! Wonderful views! "

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

Allicia W.

CA $721

CA $1,391 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Summerland-Key-Hotels-Keys-To-Paradise-95-56-Dock-Ocean-Views.h114470329.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76590000/76585900/76585831/ff61641c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/77000000/76590000/76585900/76585831/2515bc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76590000/76585900/76585831/9207bd9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76590000/76585900/76585831/8772498c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS 

[](https://www.expedia.ca/Cudjoe-Key-Hotels-WOW-Updated.h76585831.Hotel-Information)

Cudjoe Key

9.8/10

Exceptional

(28 reviews)

"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"

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

Patrick M.

CA $493

CA $971 total

includes taxes & fees

Apr 19 - Apr 20

[](https://www.expedia.ca/Cudjoe-Key-Hotels-WOW-Updated.h76585831.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/ef1e4f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/w1200h797x0y2-fa708366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/9eb0d106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/c5527e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grand Marina Suite - Poolside & Waterfront Condo

[](https://www.expedia.ca/Key-West-Hotels-Oceanfront-Oasis-Two-Bedroom-Aparthotel.h37116833.Hotel-Information)

Stock Island

9.6/10

Exceptional

(32 reviews)

"Good condo and staff help me out on phone with me till we found the condo. "

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

Raamkumaran

CA $699

CA $999 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Key-West-Hotels-Oceanfront-Oasis-Two-Bedroom-Aparthotel.h37116833.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/c532d8a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2500h1664x0y1-e1c3d816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2499h1666x1y1-3bf06910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2500h1663x0y1-0f893c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Post Card Point #319 - Ocean Views!

[](https://www.expedia.ca/Summerland-Key-Hotels-Post-Card-Point-319-Ocean-Views.h109979224.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(54 reviews)

"New furniture, and outfitting. Great view. Possibly the best location in the community. Steps from the boat ramp. "

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

Matthew K.

CA $540

CA $1,249 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Summerland-Key-Hotels-Post-Card-Point-319-Ocean-Views.h109979224.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/eacdb869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w1666h2499x1y1-3446235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2500h1666x0y1-ee87ad68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2499h1666x1y1-11741275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-2BR-In-Venture-Out-35-Dock.h116800175.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(6 reviews)

"Beautiful "

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

Lisa P.

CA $612

CA $1,255 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-2BR-In-Venture-Out-35-Dock.h116800175.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/w1170h1553x0y3-f03c7684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/49585f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/915efe13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/6d84fe3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

[](https://www.expedia.ca/Key-West-Hotels-Spacious-22-Waterfront-Condo-WPoolDock.h99341484.Hotel-Information)

Meadows

9.6/10

Exceptional

(25 reviews)

"Really enjoyed the accommodations. "

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

Timothy

CA $556

CA $1,096 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Key-West-Hotels-Spacious-22-Waterfront-Condo-WPoolDock.h99341484.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/358f9f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/0be3ab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/4660c78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/c3bbe589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aquaria House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Aquaria-House-At-Lunara-Bay.h74132633.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(41 reviews)

"Great house and pool! Dock is nice. The house is located close to the main highway coming into Key West and you do hear a lot of road noise. "

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

Andy T.

CA $1,096

CA $2,341 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Key-West-Hotels-Aquaria-House-At-Lunara-Bay.h74132633.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/681d666f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/682ba7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/a6298f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/fded6d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information)

Stock Island

7.6/10

Good

(31 reviews)

"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."

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

Julie

CA $355

CA $712 total

includes taxes & fees

Apr 22 - Apr 23

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.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=2026-04-07&endDate=2026-04-08&regionId=180163&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL)

Condos

[](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO)

Apartments

[](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT)

Private vacation homes

[](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=HOUSE_BOAT)

Cottages

[](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

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## Top Cow Key Hotel Reviews

![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg)

### Havana Cabana at Key West 

10/10 Excellent

"We had a great stay! The room was clean and comfortable, and the staff was very friendly and helpful throughout our visit. The pool area was one of our favorite parts—relaxing, well-maintained, and perfect to unwind. The property also felt very welcoming and had a nice atmosphere overall. The only downside was that sometimes people were speaking loudly in the hallways, which could be a bit disruptive when trying to rest. Other than that, everything was excellent and we would definitely stay here again!"

[](https://expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information)

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7ea6251e_y.jpg)

### Ibis Bay Beach Resort

4/10 Poor

"Room was pretty clean when we checked in. Housekeeping never changed our sheets. Floors where not cleaned, we had an ant feast in our bathroom every morning. A racoon jumped out of a trash can at me. View is amazing, staff was nice, low budget place to stay."

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

"Everything was "

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

![Opal Key Resort & Marina, Key West](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60_y.jpg)

### Opal Key Resort & Marina, Key West

6/10 Okay

"TV selections were poor. Did not have ABC which is a basic cable channel. Other channels very limited too. Realize you are not coming to watch TV but if you have a few days of bad weather or retire to the room early evening, nothing much to watch, no variety."

[](https://expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information)

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd_y.jpg)

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

8/10 Good

"The room was spacipus and clean"

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

![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5fd7b8bf_y.jpg)

### Margaritaville Beach House Key West

2/10 Terrible

"The worst experience I have ever had in any resort. The staff needs some lessons in manners! I wasn’t even asked how my day was when I was checking out! The room was the worst experience bathroom handle falling off every time I open the door. Noisy elevator sounds old, worn out furniture, just a few of the things that I had to endure. I tried to change rooms and was told I could not have similar room yet the room next to me was the exact same layout and only once during my stay, I saw it’s occupied! Beware this resort"

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

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/864ce9f9_y.jpg)

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

10/10 Excellent

"Everything about this property was amazing from the staff, to the clean rooms, to the pool! "

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

![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f_y.jpg)

### The Perry Hotel & Marina Key West

10/10 Excellent

"Wonderfully kept property with incredible food. Peaceful views of the marina and a great choice of background music. We will be back."

[](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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 poolside and the staff were very friendly. "

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

## Find out more about Cow 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 Cow 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 Cow Key ](https://expedia.ca/Cow-Key-Private-Vacation-Homes.d180163-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Cow Key ](https://expedia.ca/Cow-Key-Condos.d180163-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Cow Key ](https://expedia.ca/Cow-Key-Apartments.d180163-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Cow Key ](https://expedia.ca/Cow-Key-Cottages.d180163-aaCottages.Travel-Guide-Accommodation)
- [Resorts in Cow Key ](https://expedia.ca/Cow-Key-Resort-Hotels.d180163-aaResortHotels.Travel-Guide-Accommodation)
- [Houseboats in Cow Key ](https://expedia.ca/Cow-Key-Houseboats.d180163-aaHouseboats.Travel-Guide-Accommodation)
- [Guest Houses in Cow Key ](https://expedia.ca/Cow-Key-Guest-Houses.d180163-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Cow Key ](https://expedia.ca/Cow-Key-Villas.d180163-aaVillas.Travel-Guide-Accommodation)
- [B&B in Cow Key ](https://expedia.ca/Cow-Key-Bed-And-Breakfast.d180163-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Cow Key ](https://expedia.ca/Cow-Key-Apart-Hotels.d180163-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Cow Key ](https://expedia.ca/Cow-Key-RV-Parks.d180163-aaRVParks.Travel-Guide-Accommodation)
- [Cabin Rentals in Cow Key ](https://expedia.ca/Cow-Key-Cabins.d180163-aaCabins.Travel-Guide-Accommodation)
- [Hostels in Cow Key ](https://expedia.ca/Cow-Key-Hostels.d180163-aaHostels.Travel-Guide-Accommodation)
- [Motels in Cow Key ](https://expedia.ca/Cow-Key-Motels.d180163-aaMotels.Travel-Guide-Accommodation)
- [Inns in Cow Key ](https://expedia.ca/Cow-Key-Inns.d180163-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

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### What are some of the best vacation rentals that Cow Key has to offer?

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