Title: Summerland Key Vacation Rentals from $352: 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

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.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)

## Our top choices for Summerland Key vacation rentals

![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)

![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)

![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

(1 review)

"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

$1,075 nightly

$1,209 total

Feb 9 - Feb 10

Total with taxes and fees

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

(103 reviews)

"Great location. "

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

Davian k.

$405 nightly

$451 total

Feb 8 - Feb 9

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)

![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/925121e6.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)

![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)

![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.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(55 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

$413 nightly

$458 total

Feb 18 - Feb 19

Total with taxes and fees

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

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

![Smart TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.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.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(165 reviews)

"Everything was there that I needed. Very nice area for my dog."

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

Terry

$292 nightly

$324 total

Feb 15 - Feb 16

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/a7df710a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/4231ea78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/f4a6c5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

8.6/10

Excellent

(165 reviews)

"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "

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

Shawn M.

$318 nightly

$352 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.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)

![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)

### 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

(7 reviews)

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

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

elisa b.

$546 nightly

$605 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.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.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(177 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.

$431 nightly

$479 total

Feb 22 - Feb 23

Total with taxes and fees

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.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

$606 nightly

$673 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Miscellaneous](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/42e04085.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.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.Hotel-Information)

Cudjoe Key

8.0/10

Very Good

(1 review)

$267 nightly

$288 total

Mar 3 - Mar 4

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/117000000/116670000/116667100/116667062/8bf693c2.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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.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.com/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information)

Cudjoe Key

$556 nightly

$617 total

Feb 27 - Feb 28

Total with taxes and fees

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

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

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

![Smart TV](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/bfb5dd99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Cudjoe Key

9.8/10

Exceptional

(201 reviews)

"Will definitely stay here again "

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

Jeannine R.

$596 nightly

$662 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.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/105000000/104880000/104875300/104875207/2f62f857.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)

![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.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

$267 nightly

$288 total

Mar 4 - Mar 5

Total with taxes and fees

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

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/c8d44015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Cudjoe Key

10/10

Exceptional

(1 review)

"Very clean! Good location. "

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

January M.

$708 nightly

$786 total

Feb 25 - Feb 26

Total with taxes and fees

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

![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)

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

7.6/10

Good

(13 reviews)

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

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

Primeau J.

$465 nightly

$515 total

Feb 11 - Feb 12

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)

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

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

![Exterior](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/d9484c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### The Hemingway - Beach Houses Key West

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

Upper Sugarloaf Key

9.6/10

Exceptional

(8 reviews)

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

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

Jonathan L.

$1,398 nightly

$1,547 total

Feb 17 - Feb 18

Total with taxes and fees

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

![A heated pool](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/f90b085e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/w2499h1666x1y1-7f724f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/w2499h1666x1y1-164b9192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/48e93a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Saltwater Serenity #392 - Ocean Views on Cudjoe Key

[](https://www.expedia.com/Summerland-Key-Hotels-Saltwater-Serenity-392-Ocean-Views-On-Cudjoe-Key.h112975923.Hotel-Information)

Cudjoe Key

10/10

Exceptional

(9 reviews)

"The property was really nice and super clean! Easy access and quiet neighborhood."

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

VANESSA T.

$677 nightly

$751 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Saltwater-Serenity-392-Ocean-Views-On-Cudjoe-Key.h112975923.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.com/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information)

Summerland Key

9.8/10

Exceptional

(123 reviews)

"We enjoyed our stay! Great little house and location. "

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

Lisa K.

$547 nightly

$607 total

Mar 1 - Mar 2

Total with taxes and fees

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

![A heated pool](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/64bb49ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/84ed301b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/29c04407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/ac295bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

[](https://www.expedia.com/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information)

Cudjoe Key

$621 nightly

$688 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/12b8b185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/1bd7d565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/367a13e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/00933dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southern Exposure in Cudjoe Key #49

[](https://www.expedia.com/Summerland-Key-Hotels-Southern-Exposure-In-Cudjoe-Key-49.h106408131.Hotel-Information)

Cudjoe Key

7.6/10

Good

(4 reviews)

"The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay"

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

Colleen G.

$653 nightly

$681 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Southern-Exposure-In-Cudjoe-Key-49.h106408131.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/bf1a4e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/5e9a36aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/f9948293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/ccf18e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private and Exclusive Beach Getaway

[](https://www.expedia.com/Sugarloaf-Key-Hotels-Hammock-House-At-Sugarloaf-Beach.h88296003.Hotel-Information)

Sugarloaf Key

8.0/10

Very Good

(2 reviews)

"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "

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

Samat S.

$2,478 nightly

$2,742 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Sugarloaf-Key-Hotels-Hammock-House-At-Sugarloaf-Beach.h88296003.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.com/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21&regionId=6177802&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Houseboats

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Condos

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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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

Aparthotels

[](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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL)

Apartments

[](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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT)

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## Top Summerland Key Hotel Reviews

![Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill](https://images.trvl-media.com/lodging/42000000/41050000/41049600/41049569/1a914b14_y.jpg)

### Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

10/10 Excellent

"Host was communicative and quick to respond. Amenities were beautiful and enjoyable. "

[](https://expedia.com/Cudjoe-Key-Hotels-Vrbo-Property.h41049569.Hotel-Information)

![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg)

### Parmer's Resort

10/10 Excellent

"The rooms were very clean! Views were beautiful. Pool was heated the cool days we were there. The breakfast was good and fresh. Loved the afternoon tea, hot chocolate, and coffee selections. Staff were very welcoming!"

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

![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/3a7e709a_y.jpg)

### Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"What a pleasant surprise. Over a holiday weekend, our other booking had overbooked us. We scrambled, and found this suite. It’s really, an apartment.. Oh my gosh, we were so happy. It was much better than the original lodging. There were two adults, two 21 year old sons. There was plenty of room for all of us. Clean, comfortable. 25 minutes outside of Key West. The 21-year-olds are coming back and staying here for spring break with their friends. To the owners of the KOA, they better behave."

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

![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg)

### Looe Key Reef Resort

10/10 Excellent

"Room was very clean and comfortable. Small room but had a very comfortable small sofa and had an abundance of thick towels as well as beach towels. I was impressed with the room and check in/check out. "

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

![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg)

### Sugar Loaf Lodge

10/10 Excellent

"Clean, convenient location. "

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

![Charming cottages, dockage, pool, just minutes to Key West](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44_y.jpg)

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

10/10 Excellent

"Everything was really nice. Bed was a little firm for my liking but thats just me. Place was great. "

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

![Cottage with swimming pool and dockage, just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd_y.jpg)

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

10/10 Excellent

"Great location!"

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

![Old Florida Style, wrap around porch, boat basin for dockage, open water](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/60b95cd9_y.jpg)

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

10/10 Excellent

"Amazing little spot. We had an octopus show up two nights of the three we were there. I can not wait to stay again. This was PERFECT on every way. I celebrated my 40th"

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

![Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd_y.jpg)

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

10/10 Excellent

"Everything was great! "

[](https://expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h74236945.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 $352 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)

## Frequently asked questions

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- [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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