Title: Fleming Key Vacation Rentals from CA $441: Short-Term Rentals for 2026 | Expedia.ca

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# Fleming Key Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-08&endDate=2026-01-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 9 - Jan 10](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-09&endDate=2026-01-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-16&endDate=2026-01-18&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)

![Reception](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/bc5aedd4.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)

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

### Houseboat in Stock Island

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

8.8/10

Excellent

(172)

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

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

William

CA $186

CA $441 total

includes taxes & fees

Jan 11 - Jan 12

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

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/682ba7e4.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)

### 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)

"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 $346

CA $703 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)

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

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/bf68a65a.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)

### Vacation Home in Upper Sugarloaf Key

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

10/10

Exceptional

(14)

"Beautiful! Pool was amazing!"

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

Jennifer B.

CA $1,517

CA $2,692 total

includes taxes & fees

Jan 14 - Jan 15

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

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

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

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

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

### Vacation Home in Raccoon Key

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

CA $2,540

CA $4,255 total

includes taxes & fees

Jan 11 - Jan 12

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

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/53dba367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w2998h1999x1y1-68fba4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-e258b195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-09a4d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key West

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information)

9.8/10

Exceptional

(53)

"Perfect for our family! Recommend 10/10!"

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

Melissa F.

CA $312

CA $525 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/22000000/21700000/21694400/21694353/47847da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/22000000/21700000/21694400/21694353/3a581285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/22000000/21700000/21694400/21694353/62a71b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21694400/21694353/17331819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

[](https://www.expedia.ca/Key-West-Hotels-Watch-Sunsets-From-Your-Deck.h21694353.Hotel-Information)

8.8/10

Excellent

(207)

"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "

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

Juan E.

CA $173

CA $500 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-West-Hotels-Watch-Sunsets-From-Your-Deck.h21694353.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/d7a848f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-41f21691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/ea75861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-ffef9e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key West

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information)

9.2/10

Wonderful

(28)

"The property and our place was really nice. Would definitely stay again. "

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

Sarah M.

CA $314

CA $525 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.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)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/8267d923.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)

"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 $395

CA $712 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)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/1b26e0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/f25a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/3b92efe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/dfe1cfb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Suite-Bright-Hideaway.h110161419.Hotel-Information)

9.8/10

Exceptional

(26)

"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "

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

Richele

CA $410

CA $835 total

includes taxes & fees

Jan 10 - Jan 11

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Suite-Bright-Hideaway.h110161419.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/f4cb0461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/2f1a1fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/c3afe913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/d6f3b413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information)

10/10

Exceptional

(8)

"well maintained, clean, easy to access"

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

Raj P.

CA $2,072

CA $3,942 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/22000000/21700000/21698800/21698783/70aa44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21698800/21698783/3bed6803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/22000000/21700000/21698800/21698783/0b4bbe5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21698800/21698783/e189dfc6.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-W-Balcony.h21698783.Hotel-Information)

9.4/10

Exceptional

(133)

"This was a wonderful place to stay. We had a great time and it was convenient to reach downtown from here. Will stay again"

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

Bess Y.

CA $449

CA $887 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Key-West-Hotels-Sunrise-Suites-Condo-W-Balcony.h21698783.Hotel-Information)

![TV, stereo, offices](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/222d03ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/7fca46e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/65c00493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/b4df8eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Floralee-House-At-Lunara-Bay.h109290613.Hotel-Information)

9.8/10

Exceptional

(8)

"Amazing house! Spacious, great pool, & good location "

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

Paige G.

CA $1,448

CA $3,152 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-West-Hotels-Floralee-House-At-Lunara-Bay.h109290613.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)

"Nice place "

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

Pawel

CA $871

CA $1,330 total

includes taxes & fees

Jan 11 - Jan 12

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

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

![Marina](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/7337f89c.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)

### 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

(111)

"Great value stay"

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

Mike B.

CA $247

CA $523 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)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/ffafb3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/79dfbbb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/b8a0e487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/4208332e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stock Island

[](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.Hotel-Information)

10/10

Exceptional

(37)

"Awesome! Would stay here again!"

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

Rebecca W.

CA $498

CA $1,069 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/b52b5b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/cc36095d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/519603c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/ec2635f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Palmgale-Estate-At-Lunara-Bay.h109290608.Hotel-Information)

10/10

Exceptional

(8)

"Very clean and stocked. Pleasant experience!"

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

Iris H.

CA $1,448

CA $3,152 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Key-West-Hotels-Palmgale-Estate-At-Lunara-Bay.h109290608.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)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d36ebeba.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 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)

"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 $437

CA $894 total

includes taxes & fees

Jan 11 - Jan 12

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

![Beach](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/ef1e4f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/c5527e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/0e3ccb71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/9eb0d106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Stock Island

[](https://www.expedia.ca/Key-West-Hotels-Oceanfront-Oasis-Two-Bedroom-Aparthotel.h37116833.Hotel-Information)

9.6/10

Exceptional

(30)

"Good condo and staff help me out on phone with me till we found the condo. "

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

Raamkumaran

CA $898

CA $1,240 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Key-West-Hotels-Oceanfront-Oasis-Two-Bedroom-Aparthotel.h37116833.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)

![Exterior](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481150/01f15495.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)

### 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)

"We really enjoyed the property. "

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

Shayna

CA $249

CA $523 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Key-West-Hotels-ROYAL-PALM-STUDIO-Lovable-Studio-W-Community-Pool-Close-To-Town.h76481150.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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## Find vacation rentals that suit your style

Aparthotels

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Villas

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Apartments

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Cottages

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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=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&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=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&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=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=HOUSE_BOAT)

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## Top Fleming Key Hotel Reviews

![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)

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

### Beachside Resort & Residences

10/10 Excellent

"Great property, super clean, large, comfortable room, super friendly staff. Restaurant options were great, as well. Definitely recommend highly"

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

"4th time staying, great staff, location "

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

![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

"Fun and safe "

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

![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg)

### DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Nice property."

[](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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

"Rooms are spacious with microwave and fridage. Clean and great location. Hotel provides shuttle to downtown. Staff is amazing"

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

"Positives: only a mile from the airport; free shuttle to and from airport and downtown: good food. Beautiful beach across the street that wasn’t crowded. Rooms were pretty nice; pieces of the property were tired (fencing, walkways) but not a deal breaker. Neutral: you will hear airport noise. This didn’t bother us, but you will occasionally get a rumble from a jet. Negative: not near downtown. We traveled with younger kids, so it was fine. If you’re looking for hustle and bustle of downtown, this isn’t your place. You’re only 2.5-3 miles from Duval St. They cleaned our room late in the day (after 3). We had to call and ask for sheets for pull out couch and more towels on the first night. Other than this, service was as excellent and staff was friendly. We will return. "

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

![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

"We had an amazing day at the bungalows. Our room was clean and spacious! Several pools on property. Would stay here again. Can’t wait to come back. "

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

"Nice rooms and great pool. Great atmosphere. "

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