Title: Summerland Key Vacation Rentals from CA $555: Short-Term Rentals for 2026 | Expedia.ca

[Summerland Key Travel Guide](https://expedia.ca/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.ca/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Summerland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.ca/Summerland-Key.d6177802.Destination-Travel-Guides)

![Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6177802&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=6177802&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=6177802&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=6177802&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 Summerland Key vacation rentals

![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/925121e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/ce4bddc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.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.h73238505.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(56 reviews)

"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."

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

Raj

CA $279

CA $555 total

includes taxes & fees

Apr 2 - Apr 3

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.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)

![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)

![Pool](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fa9fff97.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 $248

CA $443 total

includes taxes & fees

Mar 27 - Mar 28

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

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/ce42ac53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/20868446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/2f62f857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Endless Summer Hideaway - lot 181

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information)

Cudjoe Key

CA $234

CA $413 total

includes taxes & fees

Mar 27 - Mar 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.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)

![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)

![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)

### 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 $310

CA $626 total

includes taxes & fees

Mar 29 - Mar 30

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

![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/e3bc7bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/c8330712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/fc5e8fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/2c15f130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Endless Ocean Views - RV589

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information)

Cudjoe Key

CA $268

CA $456 total

includes taxes & fees

Mar 27 - Mar 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/6b5c5ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/548e5f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/8235caf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/425cb8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seabreeze Escape WF RV Lot 489

[](https://www.expedia.ca/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.Hotel-Information)

Cudjoe Key

8.0/10

Very good

(1 review)

CA $234

CA $413 total

includes taxes & fees

Mar 27 - Mar 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2720h1531x0y0-d54bbbc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2641h1530x1y4-f00b5aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2722h1530x2y6-b30f2be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | Garden view](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w1153h1530x0y2-2909ca24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Atlantic View Luxury Villa with Pool

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

Summerland Key

10/10

Exceptional

(2 reviews)

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

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

Preetam

CA $774

CA $1,413 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/166b3fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/5ff4b852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/e990b643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/88788395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Oasis \~ YOUR Paradise awaits in Venture Out Resort!

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information)

Cudjoe Key

9.6/10

Exceptional

(14 reviews)

"The owners were fantastic to deal with and the house was great. "

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

Anonymous traveller

CA $193

CA $509 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/78d41425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/03f59755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/359e6f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/611ec5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kelly's Kabin - Adorable Private Summerland Key Cottage

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information)

Summerland Key

9.8/10

Exceptional

(123 reviews)

"Great location and Host was very helpful and responsive."

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

Dennis G.

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1268x0y0-ddb8f2af.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

[](https://www.expedia.ca/Summerland-Key-Hotels-Direct-Oceanfront-Atlantic-Side-Dockage-Pool-And-20-Miles-From-Key-West.h33483790.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 $343

CA $775 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)

![A heated pool](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/8bf693c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/09f11ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/627e8283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

[](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(1 review)

"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."

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

Cheryl V.

CA $260

CA $809 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.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)

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

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/99097ad0.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)

### 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

(9 reviews)

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

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

elisa b.

CA $275

CA $824 total

includes taxes & fees

Mar 29 - Mar 30

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.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)

### SAVE BIG $$$ APRIL! 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

(106 reviews)

"Janet and Jerry were excellent hosts and the property was perfect for our trip "

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

Shayne H.

CA $274

CA $687 total

includes taxes & fees

Apr 13 - Apr 14

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

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/50d75af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b22a7d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/bb5499e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b7dc0f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(3 reviews)

"Absolutely love it here… Randy is great to work with and always available. "

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

Jeannine R.

CA $333

CA $649 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.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)

![Beach towels](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/f6d4e696.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)

![Smart TV](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/bfb5dd99.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

(206 reviews)

"Will definitely stay here again "

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

Jeannine R.

CA $344

CA $862 total

includes taxes & fees

Apr 23 - Apr 24

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

![Beach](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/21ae09eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/58163bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/2c3a4e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/c9d78c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Florida Style, wrap around porch, boat basin for dockage, open water

[](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information)

Little Torch Key

9.6/10

Exceptional

(99 reviews)

"Wonderful family getaway"

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

Anthony V.

CA $557

CA $1,143 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/ef2b6e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/w2499h1666x1y1-110e9872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a8d925a6.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/121000000/120820000/120816900/120816897/5ca0fb60.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

8.0/10

Very good

(2 reviews)

" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."

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

jim b.

CA $311

CA $873 total

includes taxes & fees

Apr 6 - Apr 7

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

![Interior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h837x1y0-05f17a6f.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)

![Exterior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h819x1y0-b2147544.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

8.0/10

Very good

(15 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 $300

CA $659 total

includes taxes & fees

Apr 6 - Apr 7

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

![Smart TV](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/4a876812.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)

![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

(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 $482

CA $942 total

includes taxes & fees

Apr 13 - Apr 14

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

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## Find vacation rentals that suit your style

Private vacation homes

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Aparthotels

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Condos

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Houseboats

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Apartments

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Cottages

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VILLA)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CABIN)

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## Top Summerland Key Hotel Reviews

![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/a7994045_y.jpg)

### Looe Key Reef Resort

8/10 Good

"Tiki Bar had great tacos, but the services was a little slow."

[](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information)

![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/afeef809_y.jpg)

### Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Well maintained property, beautiful pool"

[](https://expedia.ca/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information)

![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964_y.jpg)

### Parmer's Resort

8/10 Good

"Within easy reach of Key West"

[](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information)

![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688_y.jpg)

### Sugar Loaf Lodge

8/10 Good

"good location"

[](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information)

![Private Oceanfront Cottage with dockage, pool just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f_y.jpg)

### Private Oceanfront Cottage with dockage, pool just minutes to Key West!

6/10 Okay

"Yes you are on the ocean, yes there are docks, and yes you are centrally located for activities. Cottage was clean but very dated and not well kept. It is not private, we had people walking and driving in and around us throughout the day. We did bring a dog, which is why we liked the private description, but it was not and he spent a lot of time barking when we were there. Duct tape around windows and doors, note saying you cant turn the AC below 75\. I live in Wisconsin and keep mine cooler than that! The pools were located in such a way as I felt rude using them. Grill, is a little propane weber fold up, not really what you expect. Definitely could use some upgrades and better description."

[](https://expedia.ca/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information)

![Private Secluded Ocean View & Pool Near Key West](https://images.trvl-media.com/lodging/58000000/57870000/57865200/57865163/w2304h1532x8y4-5bab2d17_y.jpg)

### Private Secluded Ocean View & Pool Near Key West

2/10 Terrible

"The pictures we received at the time we rented this property were grossly misrepresented.We were told it was a gated property. When we pulled up, the gate waa wide open..it did not work at all.The main door to enter the house locked; however, there were two other doors that were wide open when we entered as the locks were broken.It is advertised as having a hot tub and heated pool. When we arrived, we were informed it was not a hot tub but a spillover into the pool. The thermostat on the pool said 104, but the water temperature waa 70 degrees.The outside of the property has been poorly taken care of. Broken chairs near the pool, mildew buildup on the fence, trash everywhere, and black mold on the "extra" apartment on the property. The house is advertised to sleep 10 and said the couch opened up into a bed. The couch does not open up. There werent even 10 chairs to sit on or 10 forks to eat from.We would not stay here again."

[](https://expedia.ca/Summerland-Key-Hotels-Private-Secluded-Ocean-View-Pool-Near-Key-West.h57865163.Hotel-Information)

![Old Florida Style, wrap around porch, boat basin for dockage, open water](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/21ae09eb_y.jpg)

### Old Florida Style, wrap around porch, boat basin for dockage, open water

10/10 Excellent

"This was a beautiful home! We truly enjoyed our stay and the beautiful view from the home! We will be back! "

[](https://expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information)

![Charming cottages, dockage, pool, just minutes to Key West](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194_y.jpg)

### Charming cottages, dockage, pool, just minutes to Key West

8/10 Good

"Value for money: Fair This is a unit in a 3-unit divided house, not a cottage as described. It was clean, comfortable, quiet, and a good size, located a convenient drive to Key West. We enjoyed our stay."

[](https://expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

![Canal front, dockage, 2 bedroom,  2 bath](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/94e4b670_y.jpg)

### Canal front, dockage, 2 bedroom, 2 bath

2/10 Terrible

"Nice community, not far from Key West. However the house was not clean. The sheets and pillows had blood on them and looked like they had not been washed, there was a lot of dust and floors were not vacuumed properly. The bathrooms had hair on the walls. This resulted in us having to sleep on top of blankets we brought with us. "

[](https://expedia.ca/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information)

## Find out more about Summerland 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 Summerland 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 Summerland Key ](https://expedia.ca/Summerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Condo Rentals in Summerland Key ](https://expedia.ca/Summerland-Key-Condos.d6177802-aaCondos.Travel-Guide-Accommodation)

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- [Hotels in Palm Beach](https://expedia.ca/Palm-Beach-Hotels.d9061.Travel-Guide-Hotels)
- [Hotels in Naples](https://expedia.ca/Naples-Hotels.d602724.Travel-Guide-Hotels)
- [Hotels in Daytona Beach](https://expedia.ca/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [Hotels in Marco Island](https://expedia.ca/Marco-Island-Hotels.d8812.Travel-Guide-Hotels)
- [Hotels in West Palm Beach](https://expedia.ca/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels)
- [Hotels in Fort Myers](https://expedia.ca/Fort-Myers-Hotels.d602729.Travel-Guide-Hotels)
- [Hotels in Sarasota](https://expedia.ca/Sarasota-Hotels.d602719.Travel-Guide-Hotels)

Flights

- [Flights to Sarasota](https://expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)
- [Flights to Fort Myers](https://expedia.ca/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Flights to Daytona Beach](https://expedia.ca/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Flights to Cape Canaveral](https://expedia.ca/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights)
- [Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)

Cars

- [Car rentals in Fort Myers](https://expedia.ca/Car-Rentals-In-Fort-Myers.d602729.Car-Rental-Guide)

Activities

- [Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities)
- [Things to do in Boynton Beach](https://expedia.ca/Things-To-Do-In-Boynton-Beach.d6253.Travel-Guide-Activities)
- [Things to do in Fort Myers](https://expedia.ca/Things-To-Do-In-Fort-Myers.d602729.Travel-Guide-Activities)
- [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities)
- [Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)
- [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)
- [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities)
- [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

Packages

- [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

Vacation Rentals

- [Naples Rentals](https://expedia.ca/Naples-Vacation-Rentals.d602724.Travel-Guide-VacationRentals)

General

- [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549)

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