Title: Fleming Key Vacation Rentals from $313: Search Short-Term Rentals | Expedia.com

[Fleming Key Travel Guide](https://expedia.com/Fleming-Key.dx180162)[Hotels in Fleming Key](https://expedia.com/Fleming-Key-Hotels.d180162.Travel-Guide-Hotels)[Flights to Fleming Key](https://expedia.com/Cheap-Flights-To-Fleming-Key.d180162.Travel-Guide-Flights)[Car Rentals in Fleming Key](https://expedia.com/Car-Rentals-In-Fleming-Key.d180162.Car-Rental-Guide)[Fleming Key Vacation Packages](https://expedia.com/Fleming-Key.d180162.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.com/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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-07-10&endDate=2026-07-12&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

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/87c78511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/f7550de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/99362c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003026/05b75118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Stock Island

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

$662 nightly

$745 total

Mar 24 - Mar 25

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/a03560e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/2ea056a2.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)

### Vacation Home in Upper Sugarloaf Key

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

10/10

Exceptional

(14 reviews)

"Beautiful! Pool was amazing!"

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

Jennifer B.

$1,699 nightly

$1,880 total

Mar 24 - Mar 25

Total with taxes and fees

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

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/4d522535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/02900870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/b47188e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/ad59ca22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

9.8/10

Exceptional

(29 reviews)

"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 traveler

$1,541 nightly

$1,710 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/c6ea30d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/6b75217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w508h683x258y0-ac1b0fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w905h683x60y0-701bb32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stock Island

[](https://www.expedia.com/Key-West-Hotels-Paradise-Found.h79683240.Hotel-Information)

9.8/10

Exceptional

(33 reviews)

"Great house and location. We have found our rental for our yearly stay in Key West. "

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

Elizabeth F.

$664 nightly

$737 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Paradise-Found.h79683240.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)

![Exterior](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/fded6d82.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.com/Marathon-Hotels-Viking-Yacht-Getaway-In-The-Keys.h92965988.Hotel-Information)

7.6/10

Good

(31 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

$496 nightly

$550 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Marathon-Hotels-Viking-Yacht-Getaway-In-The-Keys.h92965988.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/86f4f5b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/214e4ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/9522f7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/cf0cd87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Springtide-House-At-Lunara-Bay.h74132637.Hotel-Information)

9.6/10

Exceptional

(44 reviews)

"It was great. House was amazing"

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

Ernest H.

$1,541 nightly

$1,710 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Springtide-House-At-Lunara-Bay.h74132637.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)

![Marina](https://images.trvl-media.com/lodging/38000000/37120000/37116900/37116833/w1200h797x0y2-fa708366.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)

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

### Condo in Stock Island

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

9.6/10

Exceptional

(32 reviews)

"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

$561 nightly

$623 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

![Interior](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/44ae2c6a.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)

### Houseboat in Stock Island

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

9.8/10

Exceptional

(49 reviews)

"everything was perfect"

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

Kathy A

$476 nightly

$529 total

Mar 23 - Mar 24

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/2885e075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/8d434b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/33a62704.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/75000000/74140000/74132700/74132624/3593d5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information)

10/10

Exceptional

(22 reviews)

"The perfect House , everything was good "

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

CARLOS G.

$1,541 nightly

$1,710 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/721053af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Comfort Cabin | Living area | 40-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/c267004f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Stock Island

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

9.0/10

Wonderful

(181 reviews)

"Great stay better than we expected "

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

Jordan

$298 nightly

$335 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003138/3f76db72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003138/w2994h2000x6y0-61040aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003138/364b0f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003138/81d7f208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Key West

[](https://www.expedia.com/Key-West-Hotels-Ocean-Front-2BR-Residence.h109003138.Hotel-Information)

$1,147 nightly

$1,291 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Ocean-Front-2BR-Residence.h109003138.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/358f9f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/4660c78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/c3bbe589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132633/0be3ab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Aquaria-House-At-Lunara-Bay.h74132633.Hotel-Information)

9.8/10

Exceptional

(41 reviews)

"Our family had a wonderful time at this location. Fishing off the dock and swimming was fun for the kids. A quiet location with a short drive to all attractions."

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

Nola S.

$1,541 nightly

$1,710 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Aquaria-House-At-Lunara-Bay.h74132633.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/8cb43281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/99a0cc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/be2289b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132667/a041aa61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Evershore-Estate-At-Lunara-Bay-Wellness-Home.h74132667.Hotel-Information)

9.8/10

Exceptional

(27 reviews)

"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.

$1,541 nightly

$1,710 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Evershore-Estate-At-Lunara-Bay-Wellness-Home.h74132667.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)

![Exterior](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/4208332e.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)

### Apartment in Stock Island

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

10/10

Exceptional

(38 reviews)

"Super clean "

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

Vicki A.

$902 nightly

$1,002 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/28000000/27420000/27411000/27410972/34057186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

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

9.2/10

Wonderful

(107 reviews)

"Wonderful stay with great unit and amenities. Host was fabulous and very accommodating. Plan to visit again. Highly recommend "

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

Cheryl P.

$570 nightly

$632 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/af555929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/0cb8b28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/b9eb00fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/86a497b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Key West

[](https://www.expedia.com/Key-West-Hotels-Two-Bedroom.h83022015.Hotel-Information)

9.2/10

Wonderful

(42 reviews)

"Very enjoyable other than the rooster started crowing at 4:30 AM."

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

Carol

$596 nightly

$662 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Two-Bedroom.h83022015.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/7012387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/252a4247.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/7dbae7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/8c73f51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Spindrift-House-At-Lunara-Bay.h74132659.Hotel-Information)

10/10

Exceptional

(29 reviews)

"Easy checkin and checkout. Host quickly responded to any questions. Home was comfortable and provided an enjoyable and safe place to celebrate a birthday with girlfriends. "

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

Debbie C.

$1,541 nightly

$1,710 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Spindrift-House-At-Lunara-Bay.h74132659.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/89000000/88340000/88333800/88333749/2d77d65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88340000/88333800/88333749/2a244b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88340000/88333800/88333749/d4d0ccd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/89000000/88340000/88333800/88333749/f9d2dc2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Meadows

[](https://www.expedia.com/Key-West-Hotels-Spacious-Updated-Waterfront-Condo.h88333749.Hotel-Information)

9.6/10

Exceptional

(42 reviews)

"Clean app and nice communication host"

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

Roberto

[](https://www.expedia.com/Key-West-Hotels-Spacious-Updated-Waterfront-Condo.h88333749.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/w1170h1553x0y3-f03c7684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/49585f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/915efe13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99350000/99341500/99341484/6d84fe3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Meadows

[](https://www.expedia.com/Key-West-Hotels-Spacious-22-Waterfront-Condo-WPoolDock.h99341484.Hotel-Information)

9.8/10

Exceptional

(24 reviews)

"Really enjoyed the accommodations. "

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

Timothy

$672 nightly

$746 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Spacious-22-Waterfront-Condo-WPoolDock.h99341484.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/f12238b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/a6d00a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/74f74be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/02e9b6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.com/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.Hotel-Information)

9.6/10

Exceptional

(42 reviews)

"The house was perfect for our family. The Brightwild hosts were amazing. Great location! Also, if you have little kids def use BabyQuip. We used Molly and I can’t saw enough good things about her. We will be back! "

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

Gina H.

$1,988 nightly

$2,208 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.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.com/Hotel-Search?startDate=2026-04-04&endDate=2026-04-05&regionId=180162&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=COTTAGE)

Private vacation homes

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Aparthotels

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Condos

[](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=CONDO)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=HOUSE_BOAT)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America&regionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=APARTMENT)

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## Top Fleming Key Hotel Reviews

![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5fd7b8bf_y.jpg)

### Margaritaville Beach House Key West

10/10 Excellent

"Outdoor pool was smaller and more crowded feeling than I expected. There were small bugs in the bathroom. However we had ocean front room with balcony and that was great. Room was spacious and very comfortable."

[](https://expedia.com/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.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

"The pier house continues to be my favorite go to resort on the island . The location , pool, little private beach area , 0 Duval restaurant, chart room , spa , hair salon , etc all make this property hard to beat ! Levi and all the other wonderful staff are always so helpful and pleasant . I really love everything about the pier house. Book it you will be happy you did ! "

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

![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/cf132c1e_y.jpg)

### Parrot Key Hotel & Villas

6/10 Okay

"More menu items and better/frequent room cleaning."

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

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/a1e6ec60_y.jpg)

### Beachside Resort & Residences

6/10 Okay

"It was ok. The pool area was average at best. There's a huge area to one side of the pool that was empty. It should have been filled with loungers because there weren't enough and they were a bit ratty and not very comfortable. Could have cleaned the leaves out of the pool and whirlpool better as well. When I arrived, I was told the elevator was out. Then I asked where I was and it was rm 433...only 3 flights of stairs. Never got fixed the days I was there. Never even saw anyone working on it. I'm not an invalid but the guy telling me oh it's only 3 flights wasn't helpful. He offered to have someone take my bag but, how about fix the damn elevator. Night Kayak was great and food was decent in the restaurant but a bit pricey."

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

"Clean room, excelent breakfast"

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

![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg)

### Havana Cabana at Key West 

10/10 Excellent

"Nice tropical feel . The rooms were clean , pool was beautiful. Food was excellent. "

[](https://expedia.com/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information)

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd_y.jpg)

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

10/10 Excellent

"Beautiful property "

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

![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cc507b47_y.jpg)

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

10/10 Excellent

"It’s totally awesome. The people there were outstanding hospitality was amazing so friendly. The pool was gorgeous and you have shuttles that go to the beach and go to town every hour and pick you up. Every hour rooms clean great time and love of those warm chocolate chip cookies amazing."

[](https://expedia.com/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information)

![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg)

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

8/10 Good

"Outside building was great. Could improve with room maintenace. Our room was ocean view, but toilet fil valve was broken, and takes 30 minutes wait to flush. Window frame paint was peeling. Otherwise its a great place."

[](https://expedia.com/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information)

## Find out more about Fleming Key

**Everything you need to know about Fleming Key vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fleming Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Fleming Key vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Fleming Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Fleming Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $313 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Fleming Key rentals**

At Expedia, we put the best Fleming Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Fleming Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fleming Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fleming Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Fleming Key ](https://expedia.com/Fleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Resorts in Fleming Key ](https://expedia.com/Fleming-Key-Resorts.d180162-aaResorts.Travel-Guide-Accommodation)
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- [Saint Mary Star of the Sea](https://expedia.com/Saint-Mary-Star-Of-The-Sea-Old-Town-Key-West.d553248621532652618.Vacation-Attraction)
- [Key West Lighthouse and Keeper's Quarters Museum](https://expedia.com/Key-West-Lighthouse-And-Keepers-Quarters-Museum-Old-Town-Key-West.d501383.Vacation-Attraction)
- [Duval Street](https://expedia.com/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction)
- [Clarence S. Higgs Memorial Beach Park](https://expedia.com/Clarence-S-Higgs-Memorial-Beach-Park-Old-Town-Key-West.d6246822.Vacation-Attraction)
- [Mallory Square](https://expedia.com/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction)
- [Smathers Beach](https://expedia.com/Smathers-Beach-Beachside.d6069255.Vacation-Attraction)
- [Southernmost Point](https://expedia.com/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction)
- [Key West Butterfly and Nature Conservatory](https://expedia.com/Key-West-Butterfly-And-Nature-Conservatory-Old-Town-Key-West.d6068597.Vacation-Attraction)
- [Key West Cemetery](https://expedia.com/Key-West-Cemetery-Old-Town-Key-West.d6068615.Vacation-Attraction)
- [Ernest Hemingway Home and Museum](https://expedia.com/Ernest-Hemingway-Home-And-Museum-Old-Town-Key-West.d501376.Vacation-Attraction)
- [Key West Shipwreck Museum](https://expedia.com/Key-West-Shipwreck-Museum-Key-West-Historic-District.d6063545.Vacation-Attraction)
- [Harry S. Truman Little White House](https://expedia.com/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction)
- [South Beach](https://expedia.com/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction)

Vacation Rentals

- [Stock Island Vacation Rentals](https://expedia.com/Stock-Island-Vacation-Rentals.d180166.Travel-Guide-VacationRentals)

General

- [Visit Boca Chica Key](https://expedia.com/Boca-Chica-Key.dx553248635083916609)
- [Visit Stock Island](https://expedia.com/Stock-Island.dx180166)

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