Title: Fleming Key Vacation Home Rentals from CA $430: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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# Fleming Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[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)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=180162&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 four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=180162&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)

## Browse Select Fleming Key Vacation Homes

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

![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-215da3f4.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)

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

### Vacation Home in Key West

9.8/10

Exceptional

(53)

"Clean and as advertised "

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

John H.

CA $235

CA $431 total

includes taxes & fees

Dec 4 - Dec 5

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

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

![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a00c4a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a7ddb2fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Raccoon Key

CA $2,574

CA $4,266 total

includes taxes & fees

Dec 16 - Dec 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-2789293b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/cd6c698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/8590cf39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key West

9.2/10

Wonderful

(27)

"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 $235

CA $430 total

includes taxes & fees

Nov 24 - Nov 25

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

![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/65968399.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)

### Vacation Home in Upper Sugarloaf Key

10/10

Exceptional

(14)

"Excellent place to stay if you are seeking a getaway off the beaten path. Well landscaped to give privacy to each bungalow. 2 amazing piers to fish/jet ski from. The pool and grill area is a PERFECT place to cool off and escape the heat with the swim up bar. The staff even gave us coconuts to enjoy fresh from their trees. Each day we saw amazing wildlife and even had key deer visit us. We are considering booking the whole place for a family reunion. Would also make for a great corporate...

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

Robert K.

CA $1,156

CA $2,319 total

includes taxes & fees

Nov 26 - Nov 27

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

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/b05798e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/e6a3d753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/3e9dc28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/e010edc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(17)

"The perfect House , everything was good "

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

CARLOS G.

CA $1,056

CA $2,322 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132624.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/fb618b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/6584f86b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/9608f8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/7cb43e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

9.8/10

Exceptional

(28)

"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"

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

Anonymous traveller

CA $986

CA $2,224 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-Waterfront.h74132652.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.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

9.8/10

Exceptional

(115)

"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 $402

CA $864 total

includes taxes & fees

Dec 2 - Dec 3

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/393ef519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/f5bed563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/680217a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/819fae92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

9.8/10

Exceptional

(43)

"It was great. House was amazing"

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

Ernest H.

CA $986

CA $2,224 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132637.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/029d384c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/1ee4261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/46a9f358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/06da87e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(1)

"The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again."

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

Vicki L.

CA $1,268

CA $2,922 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-New-The-Crestwood-House-Heated-Pool-Parking.h96959915.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/98e970a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/5cc75497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/58396c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/46f398f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(11)

"Great house. Large space, everything you need is there. "

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

CRIMSON A.

CA $1,409

CA $3,126 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/29072b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/b679badb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/35bd9d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/9f48ed85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

9.6/10

Exceptional

(40)

"Beautiful House, super clean, perfect location "

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

carlos s.

CA $1,268

CA $2,806 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132629.Hotel-Information)

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

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

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

![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/55508c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

CA $1,979

CA $3,512 total

includes taxes & fees

Dec 7 - Dec 8

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/3bc6e3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/46c01245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/eea02479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/21ce6c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(2)

"Amazing"

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

Byron D.

CA $1,832

CA $3,751 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Sunray-Estate.h115994668.Hotel-Information)

![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/641278c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/db01ac81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/ba72c601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/8609440e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

CA $1,832

CA $3,751 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-West-Hotels-Waterfront.h115994681.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/19354712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0ce6f815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/538d3495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0255f9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

CA $1,832

CA $3,716 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information)

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

![Pool](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/1e7f74ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/d979d3d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/9f2672ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(6)

"well maintained, clean, easy to access"

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

Raj P.

CA $1,832

CA $3,661 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h108195321.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/5c412777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9b31843e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9c855c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/79b8a22d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

10/10

Exceptional

(1)

"This was a beautiful property and was everything I expected. Staff took great care making sure it was ready for us."

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

Tony H.

CA $1,832

CA $3,716 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/fd1ec856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/3c832205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/ac674f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/ca30f8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

9.8/10

Exceptional

(6)

"Awesome place definitely recommend if going to key west "

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

Brandon M.

CA $1,409

CA $3,126 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-Catchlight-House-With-Private-Pool.h107978707.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/084a7058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/778ad535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/656f7a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/2bba6568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

9.8/10

Exceptional

(27)

"The house is perfect for our family. Access to water, pool and close enough to key west!"

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

John F.

CA $1,056

CA $2,322 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132667.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270659/1a0b7a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270659/d6cd3e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270659/ab5bd7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270659/413f25a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Town Key West

10/10

Exceptional

(21)

"Luxury unit with eclectic art work. Super clean. Comfortable bed. Walking distance to many restaurants."

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

David D.

CA $166

CA $495 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-West-Hotels-Kingfish-Keep-Lively-Escape-On-Duval-Balcony.h110270659.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=2025-12-07&endDate=2025-12-08&regionId=180162&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FFleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Fleming Key Hotel Reviews

![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

"Beautiful boutique hotel. Love the art, food, and location. Wish we had stayed here the entire trip. "

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

![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg)

### The Reach Key West, Curio Collection by Hilton

10/10 Excellent

"Spacious room, staff courteous "

[](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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

"Clean nice hotel."

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

"Everything was great!"

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

"Very spacious rooms and great amenities. Loved all this Hilton had to offer like parking, guest laundry, pool, hot tub, shuttle bus to town, breakfast, and a bar by the pool. Great location for the price especially if you’re driving."

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

"Good location, nice property with outdoor games and etc. Would recommend this stay."

[](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

"Staff very welcoming and friendly. The renovations are very beautiful. Love the new di ing area. Fanatstic murals."

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

"It was great! The room was amazing! Jodi at the front desk is awesome!"

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

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

### Beachside Resort & Residences

10/10 Excellent

"enjoyed my stay. very nice room."

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

## Find out more about Fleming Key

## Fleming Key Vacation Homes information

| Number of reviews | 314 |
| --- | --- |
| Accommodation | 748 Vacation Homes |
| Lowest Price | CA $430 |
| Highest Price | CA $4,266 |

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-   [Waterpark Hotels in Meadows](https://www.expedia.ca/Meadows-Key-West-Hotels-Waterpark-Hotels.0-n553248635976471421-0-tWaterparkHotels.Travel-Guide-Filter-Hotels)
-   [Farmstay in Monroe County](https://www.expedia.ca/Monroe-County-Agritourism.d553248635976430869-aaAgritourism.Travel-Guide-Accommodation)
-   [Hotels near Papa's Pilar Rum Distillery Hemingway Rum Company](https://www.expedia.ca/Papas-Pilar-Rum-Distillery-Hemingway-Rum-Company-Hotels.0-l870999656931368960-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Schooner Western Union](https://www.expedia.ca/Schooner-Western-Union-Hotels.0-l6069261-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Studios of Key West](https://www.expedia.ca/Studios-Of-Key-West-Hotels.0-l553248621532652634-0.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in The Meadows](https://www.expedia.ca/The-Meadows-Key-West-Hotels-Pet-Friendly-Hotel.0-n553248635976482006-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [The Meadows Hotels](https://www.expedia.ca/The-Meadows-Key-West-Hotels.0-n553248635976482006-0.Travel-Guide-Filter-Hotels)

-   [Flights to Key West](https://www.expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)

-   [Key West Historic District Vacations](https://www.expedia.ca/Key-West-Historic-District.d6281809.Destination-Travel-Guides)
-   [Visit Historic Seaport](https://www.expedia.ca/Key-West-Historic-Seaport.dx553248635976383502)
-   [Visit Key West Historic District](https://www.expedia.ca/Key-West-Key-West-Historic-District.dx6281809)
-   [Key West Vacations](https://www.expedia.ca/Key-West.d1187.Destination-Travel-Guides)
-   [Mallory Square](https://www.expedia.ca/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction)
-   [All inclusive Vacation Packages Key West](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/1187/Key-West)

-   [Things to do in Key West](https://www.expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)

-   [Book Vacation Homes in Fleming Key on Expedia.com](https://www.expedia.com/Fleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)