Title: Summerland Key Vacation Rentals from $320: 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)

## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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 three 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 four 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)

## 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)

![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)

### Villa in Summerland Key

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

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

$944 nightly

$1,062 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)

![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 | 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)

![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/w3000h1968x0y0-d4c36356.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)

$755 nightly

$849 total

Mar 31 - Apr 1

Total with taxes and fees

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

![Studio, Non Smoking (Tiny House Isla) | Living area | TV, fireplace](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/0c457183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/02360473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/fbdb0a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/2cf41658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Big Pine Key

[](https://www.expedia.com/Big-Pine-Key-Hotels-Sunshine-Key-RV-Resort-Marina.h6940514.Hotel-Information)

8.8/10

Excellent

(160 reviews)

"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "

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

brenda

$305 nightly

$343 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Big-Pine-Key-Hotels-Sunshine-Key-RV-Resort-Marina.h6940514.Hotel-Information)

![Premium bedding, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/f0cbd748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms, Kitchen | Private kitchen | Mini-fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/5b1c7313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/8fcf2a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/44936e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Marathon

[](https://www.expedia.com/Marathon-Hotels-Captain-Pips-At-Knights-Key-Inn.h13209442.Hotel-Information)

9.0/10

Wonderful

(1,178 reviews)

"Very a nice place clean nice location good price"

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

Pawel

$220 nightly

$245 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Marathon-Hotels-Captain-Pips-At-Knights-Key-Inn.h13209442.Hotel-Information)

![1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/dee083de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/2ece49e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/cbb89b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Punta Brisa

[](https://www.expedia.com/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information)

8.6/10

Excellent

(308 reviews)

"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"

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

Peter

$304 nightly

$342 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/0e99b193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/986d0b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/db48b475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/7d7ded0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Key West

[](https://www.expedia.com/Key-West-Hotels-Ocean-Front-One-Bedroom-Residence.h109003218.Hotel-Information)

$787 nightly

$885 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Ocean-Front-One-Bedroom-Residence.h109003218.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120760000/120752400/120752386/38c43601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House, Patio, Pool View | Private kitchen](https://images.trvl-media.com/lodging/121000000/120760000/120752400/120752386/d4816f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120760000/120752400/120752386/666fa05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House, Patio, Pool View | Blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/121000000/120760000/120752400/120752386/35f44104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Town Key West

[](https://www.expedia.com/Key-West-Hotels-Contra-House-Key-West.h120752386.Hotel-Information)

$1,417 nightly

$1,594 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Contra-House-Key-West.h120752386.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/721053af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/3a268cdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/bc5aedd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/2a7c6e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Stock Island

[](https://www.expedia.com/Key-West-Hotels-Aqua-Lodges-At-Hurricane-Hole-Marina.h89832384.Hotel-Information)

9.0/10

Wonderful

(181 reviews)

"Unique place to stay! We loved the nature and the location! "

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

Sara

$346 nightly

$389 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Aqua-Lodges-At-Hurricane-Hole-Marina.h89832384.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/b85cd3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/5e338074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/ee43d350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/93c22143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

$2,555 nightly

$2,875 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/2a1c9fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/5ac36685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/a11dab24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/eafa7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information)

$2,555 nightly

$2,875 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/87c78511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/c6062e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/f7550de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Stock Island

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

10/10

Exceptional

(3 reviews)

"Nice place "

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

Pawel

$907 nightly

$1,021 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/a2623807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/506c248d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/9c641387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/w3000h2208x0y0-ddab4161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.Hotel-Information)

$2,078 nightly

$2,338 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.Hotel-Information)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/d15d3c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/493aac8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/105adf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/6ec081bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Capmar-House-By-Brightwild-Huge-Home-Pool.h109003077.Hotel-Information)

10/10

Exceptional

(1 review)

"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"

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

Karen

$1,639 nightly

$1,844 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Capmar-House-By-Brightwild-Huge-Home-Pool.h109003077.Hotel-Information)

![House | Private kitchen](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/bac07b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/44733879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/c65c6ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/6ffc39a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-New-Altair-House-By-Brightwild-Pool-Pets.h109003165.Hotel-Information)

$2,246 nightly

$2,527 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-New-Altair-House-By-Brightwild-Pool-Pets.h109003165.Hotel-Information)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/2b4d6bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/3a329e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/e6748788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/088984dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-The-Joyrise-House-At-Solaire-Lunara-Bay.h120239522.Hotel-Information)

$2,304 nightly

$2,593 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-The-Joyrise-House-At-Solaire-Lunara-Bay.h120239522.Hotel-Information)

![House | Private kitchen](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/d7ba35f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/8c3abb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/26314ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 6 bedrooms, Internet](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/fbe89a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Brand-New-The-Greenmoor-House-With-Pool.h120237469.Hotel-Information)

$2,555 nightly

$2,875 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Brand-New-The-Greenmoor-House-With-Pool.h120237469.Hotel-Information)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/4fccee84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/e41447b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/bff6435e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/e2cc27c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h109003214.Hotel-Information)

$2,247 nightly

$2,528 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h109003214.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/f42e4485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/4a4c96ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 8 bedrooms, Internet](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/208a6937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/53f90a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117995431.Hotel-Information)

$2,555 nightly

$2,875 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117995431.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/ede871b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 5 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/6e0e4244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 5 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/a1098e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 5 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/05d138f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Mirador-House-By-Brightwild-Pool-Dock.h109003083.Hotel-Information)

$2,635 nightly

$2,964 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Mirador-House-By-Brightwild-Pool-Dock.h109003083.Hotel-Information)

![Apartment | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003066/02cdea53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003066/0d26fc1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003066/2501990f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003066/d6f9753c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Key West Historic District

[](https://www.expedia.com/Key-West-Hotels-Commodore-S-Cove-By-Brightwild-Epic-Location.h109003066.Hotel-Information)

$1,723 nightly

$1,938 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Commodore-S-Cove-By-Brightwild-Epic-Location.h109003066.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=2026-03-20&endDate=2026-03-21&regionId=6177802&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=VACATION_HOME)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=HOUSE_BOAT)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=CONDO)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=COTTAGE)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=APARTMENT)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=VILLA)

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=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=APART_HOTEL)

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## Top Summerland Key Hotel Reviews

![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

"Greeted by very friendly staff and the room was very clean and spacious and came with everything you would need for your stay. All staff was very nice and accommodating. Lots to do around the area and only 30 minutes away from Key West. Would definitely stay here again!"

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

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

### Sugar Loaf Lodge

8/10 Good

"It was a time capsule! If you like the '70's vib, it is great. The rooms were clean. The pool was clean. Great location! The tiki bar hasn't been used as a bar in a long time. However, it was a nice place to sit and have a morning coffee. Oh, The views were awesome!"

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

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

### Looe Key Reef Resort

6/10 Okay

"Hotel was old but clean. The Tiki hut bar is right there in the middle so when they have a band or music playing then you will be hearing it until they are done late night. Had cold Ac and hot shower so basically what is needed."

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

![Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1435x0y0-13878f9b_y.jpg)

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

6/10 Okay

"Property needed some TLC that would make the property much more adventurous. "

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

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)

![Relax by Florida Keys Beaches, just a 7-min drive away](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/7fa52371_y.jpg)

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

8/10 Good

"Quiet area on the water. Unfortunately it was chilly weather and could not fully enjoy the amenities. I would stay here again. "

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

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

### Parmer's Resort

10/10 Excellent

"Beautiful property! Location was perfect for more laid back"

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

![SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!](https://images.trvl-media.com/lodging/97000000/96270000/96267500/96267436/w902h683x61y0-db678eab_y.jpg)

### SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

10/10 Excellent

"Very well managed property-pool was lovely and just the right temperature Quiet but very convenient to restaurants, etc, Host was very receptive to questions Grilled out x3 just outside front door ! All in all an excellent stay Will recommend to our friends for sure"

[](https://expedia.com/Summerland-Key-Hotels-SEA-SHELL-COTTAGE-UNIT-2.h96267436.Hotel-Information)

![Cottage with Pool  and Boat Dockage just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/761d8c20_y.jpg)

### Cottage with Pool and Boat Dockage just minutes to Key West!

10/10 Excellent

"Great house, so clean Nicole was so pleasant and responsive "

[](https://expedia.com/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.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 $320 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

- Trending destinations on Expedia.com
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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [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

### Can I find vacation rentals in Summerland Key?

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### How many vacation rentals are there in Summerland Key?

### What can I see and do in Summerland Key?

### What are vacation rentals like in Summerland Key?

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Hotels

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