Title: Sugarloaf Key Vacation Rentals from CA $433: Short-Term Rentals for 2026 | Expedia.ca

[Sugarloaf Key Travel Guide](https://expedia.ca/Sugarloaf-Key.dx183126)[Hotels in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)[Flights to Sugarloaf Key](https://expedia.ca/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights)[Things to do in Sugarloaf Key](https://expedia.ca/Things-To-Do-In-Sugarloaf-Key.d183126.Travel-Guide-Activities)[Sugarloaf Key Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Key.d183126.Car-Rental-Guide)[Sugarloaf Key Vacation Packages](https://expedia.ca/Sugarloaf-Key.d183126.Destination-Travel-Guides)

![Sugarloaf Shores which includes a bay or harbor and a house](https://images.trvl-media.com/place/6270983/9dc99377-9102-4bb5-a879-e2e0b7c8a2d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6270983/9dc99377-9102-4bb5-a879-e2e0b7c8a2d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=183126&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 four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=183126&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)

## Our top choices for Sugarloaf Key vacation rentals

![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/d62d627a.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)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/f739e31d.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)

### Private and Exclusive Florida Keys Getaway

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

Upper Sugarloaf Key

10/10

Exceptional

(14 reviews)

"Beautiful! Pool was amazing!"

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

Jennifer B.

CA $745

CA $1,586 total

includes taxes & fees

Feb 25 - Feb 26

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

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/27d3efc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/ca8e91e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/e65d43dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/5018018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway with Stunning Views

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-With-Stunning-Views.h111873736.Hotel-Information)

Summerland Key

CA $556

CA $1,181 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-With-Stunning-Views.h111873736.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)

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

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/a7e2aa66.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.ca/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.

CA $1,347

CA $2,448 total

includes taxes & fees

Feb 22 - Feb 23

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

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

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

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

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/w3000h1968x0y0-d4c36356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway w Stunning Views

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

Summerland Key

CA $695

CA $1,261 total

includes taxes & fees

Mar 12 - Mar 13

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

![Pool](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/997a222a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/4ceb81fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/38c326a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/bd7a3cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private and Exclusive Beach Getaway

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-Mi-Azucar.h96894451.Hotel-Information)

Sugarloaf Key

10/10

Exceptional

(10 reviews)

"The location of the home is great, beautiful and peaceful.Enjoyed the pool."

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

Rachel N.

CA $2,033

CA $3,344 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-Mi-Azucar.h96894451.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)

![Beach nearby](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/7ebd5467.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)

![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.ca/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.

CA $2,710

CA $4,401 total

includes taxes & fees

Mar 13 - Mar 14

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

![Comfort Cabin | Living area](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/c267004f.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)

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

### Aqua Lodges at Hurricane Hole Marina

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

Stock Island

9.0/10

Wonderful

(179 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

CA $271

CA $535 total

includes taxes & fees

Mar 8 - Mar 9

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

![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/532693cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/44ae2c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/3d90235f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/017ce471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Living the Dream Key West Style

[](https://www.expedia.ca/Key-West-Hotels-Living-The-Dream-Key-West-Style.h99882182.Hotel-Information)

Stock Island

9.8/10

Exceptional

(47 reviews)

"Everything was excellent, awesome host, beautiful vacation!"

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

Jodi M.

CA $438

CA $556 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Key-West-Hotels-Living-The-Dream-Key-West-Style.h99882182.Hotel-Information)

![1 Bedroom Aqualodge # 6 Tarpon | Living area](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/dee083de.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)

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

![Exterior](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/bee23682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Wooden Bridge Resort and Marina

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

Punta Brisa

8.6/10

Excellent

(302 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

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

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

![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

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

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

Cudjoe Key

9.0/10

Wonderful

(56 reviews)

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

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

Raj

CA $339

CA $629 total

includes taxes & fees

Mar 18 - Mar 19

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

![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/136fc75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/41c85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

8.6/10

Excellent

(122 reviews)

"host answered our question. Did not know w& d was coin washer and dryer"

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

Robin D.

CA $308

CA $565 total

includes taxes & fees

Feb 24 - Feb 25

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

![Property grounds](https://images.trvl-media.com/lodging/112000000/111160000/111152500/111152457/065048f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111160000/111152500/111152457/3bb6424f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111160000/111152500/111152457/500ec1af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111160000/111152500/111152457/c89da320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Star Room Barnacle Resort

[](https://www.expedia.ca/Big-Pine-Key-Hotels-Star-Room-Barnacle-Bnb.h111152457.Hotel-Information)

Long Beach Estates

9.6/10

Exceptional

(4 reviews)

"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."

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

Robert

CA $424

CA $607 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Big-Pine-Key-Hotels-Star-Room-Barnacle-Bnb.h111152457.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)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/98e9c6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Home

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

Cudjoe Key

8.6/10

Excellent

(178 reviews)

"The property needed a deep clean, dirty AC grills, etc. space needs to be updated. It served us well as a "motel" space, but lacked the upkeep and quality for a vacation space."

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

Lyndon B.

CA $308

CA $623 total

includes taxes & fees

Feb 22 - Feb 23

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

![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/94e4b670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/8c79bc01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/bce2dd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/16e13244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

9.0/10

Wonderful

(93 reviews)

"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."

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

Jennifer D.

CA $390

CA $729 total

includes taxes & fees

Mar 9 - Mar 10

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

![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](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.ca/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

CA $770

CA $1,405 total

includes taxes & fees

Feb 22 - Feb 23

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

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

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

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

![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)

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

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

Summerland Key

9.8/10

Exceptional

(123 reviews)

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

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

Dennis G.

CA $376

CA $834 total

includes taxes & fees

Mar 1 - Mar 2

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

![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/00d34243.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)

### Spanish Queen @Venture Out, Cudjoe Key

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

Cudjoe Key

9.4/10

Exceptional

(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.

CA $479

CA $937 total

includes taxes & fees

Feb 24 - Feb 25

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

9.4/10

Exceptional

(104 reviews)

"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "

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

Lauren D.

CA $272

CA $683 total

includes taxes & fees

Feb 25 - Feb 26

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

![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/1020b125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

9.8/10

Exceptional

(83 reviews)

"The place is clean and convenient for anyone wanting to spend time on the water in the keys"

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

Ubaldo G.

CA $341

CA $771 total

includes taxes & fees

Mar 5 - Mar 6

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

![Property grounds](https://images.trvl-media.com/lodging/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)

### Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Cudjoe Key

8.8/10

Excellent

(151 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.

CA $513

CA $998 total

includes taxes & fees

Feb 23 - Feb 24

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

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## 

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## Find vacation rentals that suit your style

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Sugarloaf+Key%2C+Florida%2C+United+States+of+America&regionId=183126&latLong=24.624575%2C-81.54319&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=HOUSE_BOAT)

Private vacation homes

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Cabins

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Villas

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Sugarloaf+Key%2C+Florida%2C+United+States+of+America&regionId=183126&latLong=24.624575%2C-81.54319&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=COTTAGE)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Sugarloaf+Key%2C+Florida%2C+United+States+of+America&regionId=183126&latLong=24.624575%2C-81.54319&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Sugarloaf+Key%2C+Florida%2C+United+States+of+America&regionId=183126&latLong=24.624575%2C-81.54319&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Sugarloaf+Key%2C+Florida%2C+United+States+of+America&regionId=183126&latLong=24.624575%2C-81.54319&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=APARTMENT)

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## Top Sugarloaf Key Hotel Reviews

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg)

### Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Location on Duval very convenient. Stayed in the Bed and Bfast option in the Avalon, rooms were small but very nice. High ceilings and a ceiling fan."

[](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information)

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg)

### Ibis Bay Beach Resort

10/10 Excellent

"We had a splendid stay at the Ibis Resort. The staff were helpful, and knowledgeable. The entertainment of the birds was great. Temp of room was easy to maintain. The breakfast was the best in the Keys where we stayed. I rented a scooter which was both fun and easy to kick around town on. everything was convenient to find, and the small private beach area was quiet in the mornings."

[](https://expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information)

![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg)

### Margaritaville Beach House Key West

10/10 Excellent

"Everything was fantastic! "

[](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information)

![The Laureate Key West](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/3158543b_y.jpg)

### The Laureate Key West

10/10 Excellent

"Room was clean. Loved having 3 bedrooms with 3 bathrooms. It was perfect! Rented a 6 person golf cart through resort. Made getting around the island much easier. Will definitely stay here again."

[](https://expedia.ca/Key-West-Hotels-The-Laureate-Key-West.h27156592.Hotel-Information)

![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg)

### The Perry Hotel & Marina Key West

10/10 Excellent

"Yes Great Experience all around"

[](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information)

![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg)

### Parrot Key Hotel & Villas

10/10 Excellent

"-"

[](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information)

![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg)

### Pier House Resort & Spa

10/10 Excellent

"Amazing"

[](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information)

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg)

### Blue Flamingo Resort Key West

10/10 Excellent

"I visited Dec 18-Dec 22 and had a fantastic experience. From the check-in w/ Janae and the checkout, the experience was seamless and the attentiveness of staff was exceptional. BF was one of three or four high-end resorts that permitted guests to travel between locations which were all connected for a total of almost a half dozen pools and different vibes, depending on your mood. What was very convenient & money saving was the shuttle to the busy district on Duvall Street, etc, where all the happenings were, and it was great to have the hotel separate from all of the hustle and bustle of tourists and be able to go back to the hotel for a quiet refuge. Being one of the tallest buildings on the island, in my pics the vantage point I was able to get from the top floor of the hotel, which gave a really great view of most of the island of Key West. Being that it was the week before Christmas, BF, spared no expense or passion in ensuring that the Christmas vibe was still, merry and joyous, despite not being home. I would definitely go back and stay here and recommend to my friends and business associates."

[](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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

"Excellent "

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

## Find out more about Sugarloaf Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sugarloaf Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Best Hotels in Middle Torch Key](https://expedia.ca/Middle-Torch-Key-Hotels.d553248635975870980.Travel-Guide-Hotels)
- [Gasparilla Island Spa Hotels](https://expedia.ca/Gasparilla-Island-Hotels-Spa-Hotel.0-0-d6128516-tSpaHotel.Travel-Guide-Filter-Hotels)
- [America's Best Inns Hotels in Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park-Hotels-Americas-Best-Inns.0-0-d6160046--bAmericasBestInns.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Honeymoon Island State Park](https://expedia.ca/Cheap-Flights-To-Honeymoon-Island-State-Park.d6160046.Travel-Guide-Flights)

Cars

- [Global Rent A Car Car Rentals In Lower Sugarloaf Key](https://expedia.ca/Global-Rent-A-Car-Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908-c1062.Car-Rental-Guide-Suppliers)
- [AddCar Rental Car Rentals In Southwest Orlando](https://expedia.ca/AddCar-Rental-Car-Rentals-In-Southwest-Orlando.d553248635976470816-c1002.Car-Rental-Guide-Suppliers)
- [Express Travel Group Car Rentals In Lower Sugarloaf Key](https://expedia.ca/Express-Travel-Group-Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908-c1124.Car-Rental-Guide-Suppliers)
- [Interrent EU Car Rentals In Rockland Key](https://expedia.ca/Interrent-EU-Car-Rentals-In-Rockland-Key.d553248635976197596-c1043.Car-Rental-Guide-Suppliers)
- [Right Cars Car Rentals In Northeast Orlando](https://expedia.ca/Right-Cars-Car-Rentals-In-Northeast-Orlando.d553248635976480125-c1070.Car-Rental-Guide-Suppliers)
- [NU Car Rentals Car Rentals In Northwest Tampa](https://expedia.ca/NU-Car-Rentals-Car-Rentals-In-Northwest-Tampa.d553248635976469172-c71.Car-Rental-Guide-Suppliers)
- [minivan Car Rentals in Perico Island](https://expedia.ca/Minivan-Car-Rentals-In-Perico-Island.d553248635976194309-tMinivan.Car-Rental-Guide-Class)
- [luxury Car Rentals in Northeast Orlando](https://expedia.ca/Luxury-Car-Rentals-In-Northeast-Orlando.d553248635976480125-tLuxury.Car-Rental-Guide-Class)
- [U Save Car Rentals In South Fort Lauderdale](https://expedia.ca/U-Save-Car-Rentals-In-South-Fort-Lauderdale.d800034-c34.Car-Rental-Guide-Suppliers)
- [pickup Car Rentals in Perico Island](https://expedia.ca/Pickup-Car-Rentals-In-Perico-Island.d553248635976194309-tPickup.Car-Rental-Guide-Class)

Activities

- [Things to do in Boca Chica Key](https://expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)
- [Things to do in South Tampa](https://expedia.ca/Things-To-Do-In-South-Tampa.d6321582.Travel-Guide-Activities)

Packages

- [Normandy Shores All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/scuba-diving-vacations/641776810699194368/Normandy-Shores)

Vacation Rentals

- [Rentals in Little Torch Key](https://expedia.ca/Little-Torch-Key-Vacation-Rentals.d177498.Travel-Guide-VacationRentals)
- [Rentals in Rockland Key](https://expedia.ca/Rockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)
- [Rentals in Gasparilla Island](https://expedia.ca/Gasparilla-Island-Vacation-Rentals.d6128516.Travel-Guide-VacationRentals)

General

- [Visit Cudjoe Key](https://expedia.ca/Cudjoe-Key.dx3000430966)
- [Visit Venetian Islands](https://expedia.ca/Venetian-Islands.dx553248635976481890)
- [Visit Little Torch Key](https://expedia.ca/Little-Torch-Key.dx177498)
- [Visit Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park.dx6160046)

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