Title: Summerland Key Vacation Rentals from $413: 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 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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-07-10&endDate=2026-07-12&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

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/2d5a1a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/a360c147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/87670e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/e85f26a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.com/Cudjoe-Key-Hotels-Old-Florida-Style.h71420009.Hotel-Information)

8.8/10

Excellent

(92 reviews)

"Nice place to vacation "

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

Kevin D.

[](https://www.expedia.com/Cudjoe-Key-Hotels-Old-Florida-Style.h71420009.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)

![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)

### Villa in Summerland Key

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

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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/e1365b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/3b42facf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/012c9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/1577bf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.com/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information)

9.0/10

Wonderful

(151 reviews)

"Enjoyed the area. Not to far from Key West but far enough there wasn't a crowd"

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

Donna P.

[](https://www.expedia.com/Summerland-Key-Hotels-Quaint-Cottage.h33557696.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)

![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.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)

### Cottage in Cudjoe Key

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

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.

$408 nightly

$453 total

Mar 20 - Mar 21

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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)

### Vacation Home in Cudjoe Key

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

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.

$501 nightly

$557 total

Mar 30 - Mar 31

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)

![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)

### Vacation Home in Cudjoe Key

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

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.

$458 nightly

$508 total

Mar 21 - Mar 22

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)

![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)

![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)

![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)

### Cottage in Cudjoe Key

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

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

$506 nightly

$561 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)

![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.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)

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

### Vacation Home in Cudjoe Key

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

9.8/10

Exceptional

(85 reviews)

"The rental was super clean and beautiful."

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

christopher v.

$659 nightly

$732 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)

![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)

![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)

![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)

### Vacation Home in Summerland Key

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

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)

![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/3d9bbd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/1f10acb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Private kitchen](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/f9199920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/e1353328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Summerland Key

[](https://www.expedia.com/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information)

$812 nightly

$914 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.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)

![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/61ab05a6.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)

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

### Vacation Home in Summerland Key

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

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)

![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)

![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)

### Vacation Home in Cudjoe Key

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

9.4/10

Exceptional

(19 reviews)

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

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

Kimberly G.

$611 nightly

$679 total

Apr 13 - Apr 14

Total with taxes and fees

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/3a4f3a48.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)

### Vacation Home in Cudjoe Key

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

$615 nightly

$675 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/d62d627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

### Vacation Home in Upper Sugarloaf Key

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

10/10

Exceptional

(14 reviews)

"Beautiful! Pool was amazing!"

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

Jennifer B.

$1,699 nightly

$1,880 total

Mar 24 - Mar 25

Total with taxes and fees

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

![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)

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

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

### Vacation Home in Cudjoe Key

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

8.8/10

Excellent

(153 reviews)

"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "

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

bryan c.

$657 nightly

$729 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/8ea08bd9.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/c9d78c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Little Torch Key

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

9.6/10

Exceptional

(98 reviews)

"Wonderful family getaway"

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

Anthony V.

$749 nightly

$831 total

Mar 29 - Mar 30

Total with taxes and fees

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

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

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

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

### Vacation Home in Cudjoe Key

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

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

$589 nightly

$653 total

Mar 25 - Mar 26

Total with taxes and fees

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

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

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

![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)

### Vacation Home in Cudjoe Key

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

10/10

Exceptional

(1 review)

"Very clean! Good location. "

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

January M.

$701 nightly

$772 total

Mar 30 - Mar 31

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)

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

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

![A heated pool](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/a2e7cac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Cudjoe Key

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

10/10

Exceptional

(6 reviews)

"Beautiful "

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

Lisa P.

$938 nightly

$1,035 total

Mar 30 - Mar 31

Total with taxes and fees

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

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

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

![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.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)

### Vacation Home in Cudjoe Key

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

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)

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=2026-04-02&endDate=2026-04-03&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

[](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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VACATION_HOME)

Condos

[](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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CONDO)

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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=APART_HOTEL)

Houseboats

[](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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=HOUSE_BOAT)

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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=APARTMENT)

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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=COTTAGE)

Villas

[](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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VILLA)

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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CABIN)

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## Top Summerland Key Hotel Reviews

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

### Sugar Loaf Lodge

6/10 Okay

"Not clean bath room. Door key not works correctly."

[](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)

![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

"Great property "

[](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/a7994045_y.jpg)

### Looe Key Reef Resort

8/10 Good

"Rooms are very spacious. In our room: Small microwave and mini fridge (no freezer). Two hangers. Two luggage stands. Table and 2 chairs. On main entry side outside: Shared sidewalk and shared area with a few picnic tables or tables and chairs for outdoor seating. On canal side outside: One chair and small table. Shared narrow sidewalk/seating. Parking is a short-ish walk from your room past the Tiki Bar in the general unpaved parking lot. Looking for coffee? Visit the office. Upon check-out, we learned the owners are trying to keep the retro look and feel. Owners and staff are super friendly and helpful. Nightly activities at the Tiki Bar. Tiki Bar was located about 20-50 steps away from our front door. It was hopping on Karaoke Night and Trivia Night. The following night was very quiet. We just needed a place to sleep and it was just fine. Location was great for all of the activities we had planned."

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

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

### Parmer's Resort

10/10 Excellent

"The perfect amount of extra touches makes this property the best place to stay in the lower keys. "

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

![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

"Awesome spot"

[](https://expedia.com/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.com/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.com/Summerland-Key-Hotels-Canal-Front.h61585151.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 $413 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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- [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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