Title: Fleming Key Vacation Rentals from CA $436: Short-Term Rentals for 2026 | Expedia.ca

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# Fleming Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=180162&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 three months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=180162&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)

## Our top choices for Fleming Key vacation rentals

![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)

![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)

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

### Houseboat in Stock Island

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

8.8/10

Excellent

(172 reviews)

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

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

William

CA $258

CA $524 total

includes taxes & fees

Jan 29 - Jan 30

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

![Beach towels](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/3a198a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/79d0a981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/0fa3fcec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/8f6d84fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval.h27682303.Hotel-Information)

9.6/10

Exceptional

(415 reviews)

"We loved it here! Not very far from Duval street. "

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

Keghan J.

CA $287

CA $519 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval.h27682303.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/9d55a4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/b4eb767b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/b3743fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/6497e910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-SUGAR-PALM-STUDIO-Tranquil-Studio-W-Community-Pool-Close-To-Town.h76481154.Hotel-Information)

9.8/10

Exceptional

(112 reviews)

"Great value stay"

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

Mike B.

CA $255

CA $533 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Key-West-Hotels-SUGAR-PALM-STUDIO-Tranquil-Studio-W-Community-Pool-Close-To-Town.h76481154.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/2f8538ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/6674ae85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/0233b13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Stock Island

[](https://www.expedia.ca/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

CA $658

CA $1,098 total

includes taxes & fees

Jan 13 - Jan 14

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

![Property grounds](https://images.trvl-media.com/lodging/111000000/110620000/110612500/110612497/f1485aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/111000000/110620000/110612500/110612497/0ad20aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110620000/110612500/110612497/1c5abd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/111000000/110620000/110612500/110612497/78cb5ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Key West

[](https://www.expedia.ca/Key-West-Hotels-The-Salt-Cay-Updated-Stunning-Sunset-View.h110612497.Hotel-Information)

9.8/10

Exceptional

(39 reviews)

"Everything was great."

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

Keith

CA $373

CA $800 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-The-Salt-Cay-Updated-Stunning-Sunset-View.h110612497.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579922/7253b1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579922/deccd475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579922/19d6d37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579922/2327ff40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Rickys-Retreat-Truman-Duval-Perfect-For-A-Getaway-In-Key-West.h112579922.Hotel-Information)

9.8/10

Exceptional

(20 reviews)

"my stay was prett"

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

Amanda M.

CA $214

CA $513 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-Rickys-Retreat-Truman-Duval-Perfect-For-A-Getaway-In-Key-West.h112579922.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/28000000/27120000/27117100/27117042/9069fcfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/28000000/27120000/27117100/27117042/68df80f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117100/27117042/w495h288x0y6-1a96461e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/28000000/27120000/27117100/27117042/dd06cf96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Location.h27117042.Hotel-Information)

10/10

Exceptional

(117 reviews)

"The property was exactly as expected. Host was excellent. Great location and the bikes were great for getting around town. White Street Pizza down the street was amazing too!"

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

Joanna B.

CA $379

CA $693 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Key-West-Hotels-Location.h27117042.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285337/35e3d562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285337/w1600h1197x0y3-5c346695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285337/w1600h1197x0y3-7e1bbb90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285337/w1600h1197x0y3-d6f7a0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Rent-At-PORCHSIDE-PARADISE-Steps-To-Duval.h106285337.Hotel-Information)

8.8/10

Excellent

(75 reviews)

"PERFECT location close to everything. Really cute little place perfect for two people. We had a fantastic time!"

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

Olivia B.

CA $392

CA $748 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-Rent-At-PORCHSIDE-PARADISE-Steps-To-Duval.h106285337.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/2a05ec53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/1e6e1b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/1937bf09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/d8f8c642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Egret-Suite-Bright-Retreat.h110161406.Hotel-Information)

9.8/10

Exceptional

(36 reviews)

"Good place to stay loved it"

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

Charles I.

CA $355

CA $765 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-Egret-Suite-Bright-Retreat.h110161406.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/123000000/122650000/122643800/122643778/2dde9739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/123000000/122650000/122643800/122643778/864a61fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms](https://images.trvl-media.com/lodging/123000000/122650000/122643800/122643778/0c7ae1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122650000/122643800/122643778/e95db51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

[](https://www.expedia.ca/Key-West-Hotels-The-Grand-Cayman-Beautifully-Remodeled-Key-West-Condo.h122643778.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Excellent facility exactly as advertised."

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

Shirl c.

CA $395

CA $834 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-The-Grand-Cayman-Beautifully-Remodeled-Key-West-Condo.h122643778.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481150/d34be38d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481150/88b5790a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481150/1d2a33bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481150/edf92042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-ROYAL-PALM-STUDIO-Lovable-Studio-W-Community-Pool-Close-To-Town.h76481150.Hotel-Information)

9.4/10

Exceptional

(96 reviews)

"We really enjoyed the property. "

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

Shayna

CA $237

CA $511 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-ROYAL-PALM-STUDIO-Lovable-Studio-W-Community-Pool-Close-To-Town.h76481150.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/237d62a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/bd64b13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/55f445db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/a8959ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information)

9.0/10

Wonderful

(181 reviews)

"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "

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

ALISHA

CA $357

CA $664 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.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)

![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)

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

![Exterior](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/fded6d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Stock Island

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

7.8/10

Good

(26 reviews)

"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 $348

CA $705 total

includes taxes & fees

Jan 25 - Jan 26

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

![Interior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/5018ef84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/db32ae29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/a9dabced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/5fb3ded1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Key West

[](https://www.expedia.ca/Key-West-Hotels-Island-View-1BR-Residence-With-Balcony.h109003146.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Great place it is a full apartment with everything you could need and very clean "

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

Luis

CA $507

CA $696 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Key-West-Hotels-Island-View-1BR-Residence-With-Balcony.h109003146.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)

![Fridge, oven, stovetop, ice maker](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/9e3ecc72.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)

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

### Houseboat in Stock Island

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

9.8/10

Exceptional

(38 reviews)

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

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

Jodi M.

CA $526

CA $664 total

includes taxes & fees

Jan 12 - Jan 13

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

![Property grounds](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579938/2b7fb420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579938/4329ca76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579938/618e37df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579938/d54728a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Abbeys-Attic-Truman-Duval-Cozy-Getaway-In-The-Heart-Of-Key-West.h112579938.Hotel-Information)

9.6/10

Exceptional

(16 reviews)

"cozy and close to everything. highly recommend!!"

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

Marcia V.

CA $214

CA $509 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-West-Hotels-Abbeys-Attic-Truman-Duval-Cozy-Getaway-In-The-Heart-Of-Key-West.h112579938.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/w800h599x0y1-b3246da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/15cbea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d36ebeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d6954c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stock Island

[](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information)

9.8/10

Exceptional

(117 reviews)

"Great location, close to everything family had a great time."

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

rafael m.

CA $438

CA $903 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/28000000/27420000/27411000/27410972/1b715b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27420000/27411000/27410972/1ac3c7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27420000/27411000/27410972/a85e69c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27420000/27411000/27410972/660ba577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

[](https://www.expedia.ca/Key-West-Hotels-Quiet.h27410972.Hotel-Information)

9.2/10

Wonderful

(101 reviews)

"Fabulous view to watch the sunset and planes take off! Super comfortable stay with all the typical amenities and plenty of space. Quiet location close enough to drive/bike to everything you need without all the bustle. Margaret was an amazing, communicative host. "

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

Chloe C.

CA $595

CA $881 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-Quiet.h27410972.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112840000/112833100/112833010/80f3f26e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112840000/112833100/112833010/2f354984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112840000/112833100/112833010/b81172ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112840000/112833100/112833010/w1920h1236x0y0-b8ec3287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Key West

[](https://www.expedia.ca/Key-West-Hotels-The-Samana-Cay-Tropial.h112833010.Hotel-Information)

9.8/10

Exceptional

(25 reviews)

"This property is beautiful and the location is great as well. We will be back!"

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

Patricia K.

CA $373

CA $800 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Key-West-Hotels-The-Samana-Cay-Tropial.h112833010.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/22000000/21700000/21695300/21695258/3110879d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21695300/21695258/359b6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21695300/21695258/52fe0da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/22000000/21700000/21695300/21695258/ca16ec5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

[](https://www.expedia.ca/Key-West-Hotels-Sunrise-Suites-Condo-With-Balcony-Shared-Pool.h21695258.Hotel-Information)

9.0/10

Wonderful

(138 reviews)

"Great stay"

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

Jason U.

CA $420

CA $846 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Key-West-Hotels-Sunrise-Suites-Condo-With-Balcony-Shared-Pool.h21695258.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.ca/Hotel-Search?startDate=2026-01-25&endDate=2026-01-26&regionId=180162&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=VILLA)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=HOUSE_BOAT)

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## Top Fleming Key Hotel Reviews

![Fairfield Inn and Suites by Marriott Key West](https://images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg)

### Fairfield Inn and Suites by Marriott Key West

10/10 Excellent

"A safe in the room would be nice. Clean room, friendly staff, convenient to nearby places. I would definitely stay there again because of the convenience and location with restaurants and shopping nearby."

[](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.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

"The staff was absolutely fantastic! Highly recommend."

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

"Beautiful resort, wonderful staff, clean rooms!"

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

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

### Beachside Resort & Residences

10/10 Excellent

"Room was very clean and for someone like me who is OCD about staying somewhere clean i was very comfortable there would definitely come back !!! "

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

"Property was clean. Staff friendly, food delicious "

[](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 was very clean, and spacious. It fit our family of six perfectly. We had a 2 bedroom 2 bath. Employees were friendly and helpful. Our kids loved the pool and all of the games they had to offer pool side. There was lots of seating around the pool. Tables, beach chairs, loungers, swings facing the ocean, and a hammock. My favorite part was the little restaurant they have pool side. Super kind workers. Everything we tried was delicious. The drinks were amazing. Yes, it is next to the airport and you hear some planes a few times daily. Which didn’t bother my family at all. If we went back to Key West 100% we’d be staying here"

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

"really liked the shuttle especially for New Years Eve. Room is okay - could use some more decorations or touches. Excellent pool and grounds and welcoming staff. will stay again. "

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

"Great room, great staff"

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

![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg)

### La Concha Key West, Autograph Collection

10/10 Excellent

"Beautiful hotel, friendly staff"

[](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information)

## Find out more about Fleming 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 Fleming 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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- [Vacation Homes in Fleming Key ](https://expedia.ca/Fleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Enterprise Destinations In Canada](https://expedia.ca/Enterprise-Destinations-In-Canada.d31-c15.Car-Rental-Destination-Suppliers)

Activities

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

Packages

- [Madeira Island Vacations](https://expedia.ca/Madeira-Island.d11326.Destination-Travel-Guides)
- [Smathers Beach](https://expedia.ca/Smathers-Beach-Beachside.d6069255.Vacation-Attraction)
- [all inclusive vacations](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations)

General

- [Visit Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park.dx6160046)

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