Title: Summerland Key Vacation Rentals from $291: Search Short-Term Rentals | Expedia.com

[Summerland Key Travel Guide](https://expedia.com/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Flights to Summerland Key](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Car Rentals in Summerland Key](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.com/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 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6177802&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)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-07-24&endDate=2026-07-26&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)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.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)

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

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

Cudjoe Key

9.0/10

Wonderful

(56 reviews)

"The location was perfect for going in and out of Key West. The house was clean, spacious and comfortable. "

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

Josie D.

$359 nightly

$398 total

Apr 2 - Apr 3

Total with taxes and fees

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

![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)

![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.com/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.

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

![Deluxe Villa, Ocean View | 4 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2304h1532x8y4-86de2f42.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.com/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

$975 nightly

$1,097 total

Apr 5 - Apr 6

Total with taxes and fees

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

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/c7aff2d5.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)

![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)

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

[](https://www.expedia.com/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.

$452 nightly

$501 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.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)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.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.com/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.

$501 nightly

$557 total

Apr 3 - Apr 4

Total with taxes and fees

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/d142accd.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)

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

[](https://www.expedia.com/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 traveler

$327 nightly

$363 total

Apr 8 - Apr 9

Total with taxes and fees

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

![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.com/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.

$549 nightly

$602 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/6ca864aa.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)

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

### Endless Summer Hideaway - lot 181

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

Cudjoe Key

$273 nightly

$294 total

Mar 31 - Apr 1

Total with taxes and fees

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9e0e4056.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)

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

[](https://www.expedia.com/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.

$449 nightly

$498 total

Apr 13 - Apr 14

Total with taxes and fees

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

![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.com/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.

$415 nightly

$460 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/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)

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

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

### Spanish Queen @Venture Out, Cudjoe Key

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

Cudjoe Key

9.4/10

Exceptional

(21 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.

$615 nightly

$683 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/ccc6991c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/586730d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/5c8f33a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/2903bcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One of the very few beach houses with a daily, rental license in the Keys.

[](https://www.expedia.com/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information)

Summerland Key

8.8/10

Excellent

(67 reviews)

"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "

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

Paula D.

$1,283 nightly

$1,423 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/3f698bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/da1c9823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/fd63c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/84aef88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

[](https://www.expedia.com/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(96 reviews)

"We had a great time and will be back. "

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

Michelle K.

$697 nightly

$773 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.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)

![A heated pool](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/056b8deb.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)

![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.com/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information)

Cudjoe Key

$301 nightly

$325 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/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)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/425cb8a3.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)

![Miscellaneous](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/42e04085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seabreeze Escape WF RV Lot 489

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

Cudjoe Key

8.0/10

Very Good

(1 review)

$273 nightly

$294 total

Mar 31 - Apr 1

Total with taxes and fees

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/6db1494c.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.com/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.

$578 nightly

$634 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/b6f371a6.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.com/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(155 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.

$629 nightly

$698 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/60a3d49e.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.com/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.

$553 nightly

$614 total

Apr 24 - Apr 25

Total with taxes and fees

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

![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/e279f33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/3a4f3a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/w2500h1666x0y1-51dfe5dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/22d4a29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

[](https://www.expedia.com/Summerland-Key-Hotels-Florida-Keys-Canal-Front-2BR2BA-W-35-Seawall.h121310572.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(2 reviews)

"very good! "

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

Joseph D.

$618 nightly

$678 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Florida-Keys-Canal-Front-2BR2BA-W-35-Seawall.h121310572.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)

![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/15b239c0.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.com/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.

$562 nightly

$623 total

Apr 6 - Apr 7

Total with taxes and fees

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

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE)

Apartments

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Cabins

[](https://www.expedia.com/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CABIN)

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## Top Summerland Key Hotel Reviews

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

### Parmer's Resort

10/10 Excellent

"Everything about Parmer’s resort was great! The staff was incredibly kind and helpful, the amenities were fun, the space around rooms were filled with lots of seating and areas to relax. There was a variety of breakfast items as well. "

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

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

### Looe Key Reef Resort

10/10 Excellent

"This was a great little affordable nest that we could stay at as we explored both ends of Keys. The staff was wonderful and very accommodating. The tiki bar on the property was fun and entertaining with karaoke, trivia night, & live bands. Bed was super comfortable. Back door to the channel to watch the boats. We could do everything we wanted without spending a ton on where we stayed. Ideal for the adventurous traveler."

[](https://expedia.com/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

"Excellent breakfast, stayed in the hotel which was spotless and comfortable. Staff was very friendly...and a lot of fun. A lot of activities geared towards adults at this KOA. "

[](https://expedia.com/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.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.com/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.com/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.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

"Very nice place. Rooms were spacious. Loved the laid back feeling. "

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

![Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/3f698bba_y.jpg)

### Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8/10 Good

"We had a nice stay at Cudjoe key. We like the location of the home (in between Key West and Marathon). Views were beautiful! We enjoyed the local wildlife neighbors (lizards, pelicans, a one legged cormorant and jelly fish). Great restaurants nearby. Pool was nice and plenty of outdoor chairs for relaxing. Inside the home was as expected based on prior reviews. I would like to have had more bath towels provided. Communication and instruction from the managers good. Washer and dryer very efficient. "

[](https://expedia.com/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.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

10/10 Excellent

"Very clean and neat. All the kitchen utensils you need. Pool and docks fantastic. Top shelf "

[](https://expedia.com/Summerland-Key-Hotels-Charming-Cottages.h33548243.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.com/Summerland-Key-Hotels-Private-Secluded-Ocean-View-Pool-Near-Key-West.h57865163.Hotel-Information)

## Find out more about Summerland Key

**Everything you need to know about Summerland Key vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Summerland Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Summerland Key vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Summerland Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Summerland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $291 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Summerland Key rentals**

At Expedia, we put the best Summerland Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Summerland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Summerland Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Summerland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Summerland Key ](https://expedia.com/Summerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Summerland Key ](https://expedia.com/Summerland-Key-Cottages.d6177802-aaCottages.Travel-Guide-Accommodation)
- [RV Parks in Summerland Key ](https://expedia.com/Summerland-Key-RV-Parks.d6177802-aaRVParks.Travel-Guide-Accommodation)
- [Villas in Summerland Key ](https://expedia.com/Summerland-Key-Villas.d6177802-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Summerland Key ](https://expedia.com/Summerland-Key-Resorts.d6177802-aaResorts.Travel-Guide-Accommodation)
- [Motels in Summerland Key ](https://expedia.com/Summerland-Key-Motels.d6177802-aaMotels.Travel-Guide-Accommodation)
- [Condo Rentals in Summerland Key ](https://expedia.com/Summerland-Key-Condos.d6177802-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Summerland Key ](https://expedia.com/Summerland-Key-Cabins.d6177802-aaCabins.Travel-Guide-Accommodation)

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Hotels

- [Hotels in Fort Myers](https://expedia.com/Fort-Myers-Hotels.d602729.Travel-Guide-Hotels)
- [Hotels in Pensacola Beach](https://expedia.com/Pensacola-Beach-Hotels.d6677.Travel-Guide-Hotels)
- [Hotels in Gainesville](https://expedia.com/Gainesville-Hotels.d6048189.Travel-Guide-Hotels)
- [Hotels in Cocoa Beach](https://expedia.com/Cocoa-Beach-Hotels.d6549.Travel-Guide-Hotels)
- [Hotels in West Palm Beach](https://expedia.com/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels)
- [Oceanfront Hotels in Destin](https://expedia.com/Destin-Hotels-Oceanfront-Hotels.0-0-d6906-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Destin](https://expedia.com/Destin-Hotels.d6906.Travel-Guide-Hotels)
- [Hotels in Sarasota](https://expedia.com/Sarasota-Hotels.d602719.Travel-Guide-Hotels)
- [Hotels in Naples](https://expedia.com/Naples-Hotels.d602724.Travel-Guide-Hotels)
- [Hotels in Pensacola](https://expedia.com/Pensacola-Hotels.d6023331.Travel-Guide-Hotels)
- [Oceanfront Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels-Oceanfront-Hotels.0-0-d8021-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Key West](https://expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Daytona Beach](https://expedia.com/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [Beach Hotels in Destin](https://expedia.com/Destin-Hotels-Beach-Hotel.0-0-d6906-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Key West](https://expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels)
- [Hotels in Tallahassee](https://expedia.com/Tallahassee-Hotels.d6048214.Travel-Guide-Hotels)
- [Oceanfront Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels-Oceanfront-Hotels.0-0-d6047864-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Siesta Key](https://expedia.com/Siesta-Key-Hotels-Oceanfront-Hotels.0-0-d6881-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels)
- [Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Destin](https://expedia.com/Cheap-Flights-To-Destin.d6906.Travel-Guide-Flights)
- [Cheap Flights to Key West](https://expedia.com/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)
- [Cheap Flights to Fort Myers](https://expedia.com/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Cheap Flights to Daytona Beach](https://expedia.com/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Cheap Flights to Sarasota](https://expedia.com/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Cheap Flights to Pensacola](https://expedia.com/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights)

Cars

- [Car rentals in West Palm Beach](https://expedia.com/Car-Rentals-In-West-Palm-Beach.d2742.Car-Rental-Guide)

Packages

- [Key West Vacation](https://expedia.com/Key-West.d1187.Destination-Travel-Guides)
- [Destin Vacation](https://expedia.com/Destin.d6906.Destination-Travel-Guides)

General

- [Visit Santa Rosa Beach](https://expedia.com/Santa-Rosa-Beach.dx183118)

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