Title: Sugarloaf Key Vacation Rentals from CA $368: 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)

# Sugarloaf Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-04-10&endDate=2026-04-12&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

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/93e2a835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/dbc7418b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/ab69be49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/f9199920.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 $594

CA $1,128 total

includes taxes & fees

Dec 22 - Dec 23

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/9d9f7a21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/dcb46088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/facc5471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/587f6dd1.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-W-Stunning-Views.h111873736.Hotel-Information)

Summerland Key

CA $422

CA $1,002 total

includes taxes & fees

Dec 22 - Dec 23

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/ee961b10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/c54b4cae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/65968399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palm - Beach Houses Key West

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

Upper Sugarloaf Key

10/10

Exceptional

(14)

"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."

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

Harvey(Tabb) M.

CA $1,511

CA $2,767 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Pool](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/e8302fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/ae1e02d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/317baf78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/cba02a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lighthouse - Beach Houses Key West

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.Hotel-Information)

Upper Sugarloaf Key

9.6/10

Exceptional

(11)

"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"

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

Peter Q.

CA $1,359

CA $2,403 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.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)

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/0fd30b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hammock House - Beach Houses Key West

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

Sugarloaf Key

8.0/10

Very good

(2)

"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 $3,029

CA $4,813 total

includes taxes & fees

Dec 27 - Dec 28

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

![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/87ae302c.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)

![Beach nearby](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/8a4fe85c.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)

"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 $1,898

CA $3,152 total

includes taxes & fees

Jan 3 - Jan 4, 2026

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

![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/d6422035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Bungalow | Private kitchen](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/920119e4.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)

### Aqua Lodges at Hurricane Hole Marina

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

Stock Island

8.8/10

Excellent

(170)

"Location , staff , and aqua lodge were perfect."

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

William

CA $312

CA $582 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Kayaking](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/edd108d5.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)

![Outdoor pool](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/6c556697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/56796875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunshine Key RV Resort & Marina

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

Big Pine Key

8.8/10

Excellent

(160)

"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

CA $420

CA $473 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/681d666f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/a6298f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/6d55c844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/682ba7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information)

Stock Island

7.8/10

Good

(26)

"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."

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

Julie

CA $360

CA $713 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information)

![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)

![New Deluxe Duplex Unit, 1 Queen Bed, Unit C | Private kitchen](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/3b24927e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:30 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/bdbf7145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/1bf38821.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

(279)

"We loved it here. So beautiful and quiet."

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

Mark

CA $154

CA $368 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![Beach](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/b128ac5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/49c68fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/2cf2f4c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/442d52e2.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.h71402765.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(52)

"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "

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

Lauren R.

CA $217

CA $476 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h71402765.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.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)

![TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.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

(120)

"Jennifer was very nice and accommodating."

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

Randy G.

CA $220

CA $454 total

includes taxes & fees

Dec 21 - Dec 22

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

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/eca90904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/489ad80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![20-inch TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/45293052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/376faaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Vacation Club at Sunset Harbor, Key West

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information)

Old Town Key West

8.6/10

Excellent

(322)

"Place was great bed was comfy and the water was HOT!!! "

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

Angela

CA $462

CA $566 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information)

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

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/29403089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/f9f1343b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Cudjoe Key

8.6/10

Excellent

(164)

"Bad need of repair....rust....no boat ramp......shallow water....screened in porch was aweful with holes in the screens and lots of mosquitos and rusted grill."

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

Debra M.

CA $207

CA $393 total

includes taxes & fees

Dec 21 - Dec 22

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

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/2fb13370.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

(122)

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

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

Lisa K.

CA $279

CA $706 total

includes taxes & fees

Dec 21 - Dec 22

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

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f111b153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DECEMBER SAVE 60% OFF! 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

(101)

"Great location. "

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

Davian k.

CA $412

CA $844 total

includes taxes & fees

Jan 10 - Jan 11, 2026

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

![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/357cfc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Time #110 Ocean Views - Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information)

Cudjoe Key

9.4/10

Exceptional

(12)

"Our family had an amazing vacation! We love the house and hope to come back!! "

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

Tammy G.

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information)

![Swim-up bar](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/17e19347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2298h1530x0y2-9bfdab77.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)

![Porch](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2298h1532x0y2-24d28430.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)

"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 $776

CA $1,417 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](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/34000000/33490000/33483800/33483790/w1917h1268x0y0-ddb8f2af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/6758d3c9.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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1435x0y0-13878f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Cudjoe Key

8.8/10

Excellent

(155)

"Great location , clear communications and listing accuracy. Will be coming back again "

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

Kirk D.

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

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/28679789.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)

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

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

### DECEMBER SAVE 60% OFF 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

(82)

"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 $412

CA $844 total

includes taxes & fees

Jan 15 - Jan 16, 2026

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

![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg)

### Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"For rhe price per night, breakfast neded actual hot items... quite disappointed in breakfast selections. Price of beer at the bar is way too expensive... 7.50 for a michelob ultra?????. Beautiful property and the bungalow was very nice. Pool also very nice near the lobby/office area "

[](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information)

![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg)

### Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"EVERYTHING WAS SPECTACULAR! THE TWO LADIES AT THE LOBBY WERE SO NICE! "

[](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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

"Beautiful place, staff extremely friendly, shuttle made it easy to get around Definitely coming bac"

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

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg)

### Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Absolutely loved this resort and everything was perfect. The 2 bedroom villa as beautiful and the screen in deck was perfect! We will definitely be back! Thank you for making our anniversary great!"

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information)

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg)

### Beachside Resort & Residences

10/10 Excellent

"Amazing suite "

[](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information)

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg)

### Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"The room and amenities at Hyatt Windward were top notch!!!"

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information)

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg)

### Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent

"Yes and view was ok. Next time we will request the marina view"

[](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg)

### Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"Awesome stay. Not sure what people don’t like about the Casa. "

[](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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

"Very spacious, neat rooms. Great vibe"

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