Hotels in Midtown

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Oct 15 - Oct 16
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Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Where to stay in Midtown?

A dining table with plates of food, a drink, and a view of a pool and palm trees.
A beach with a palm tree and two chairs.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A person standing by a window overlooking a beach with palm trees and the ocean.

1. Margaritaville Beach House Key West

Margaritaville Beach House Key West
1.1 km from Midtown
United States
Paraskevi
$195
$282 total
includes taxes & fees
Oct 29 - Oct 30
Margaritaville Beach House Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

2. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.2 km from Midtown
United States
Dennis
$99
$179 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A spacious lobby with green sofas, a coffee table, and a dining area.

3. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Casa Marina, 1 km from Midtown
United States
Gregory
$216
$310 total
includes taxes & fees
Oct 25 - Oct 26
Casa Marina Key West, Curio Collection by Hilton
A beach with a wooden pier, palm trees, and beach umbrellas.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables and chairs, overlooking the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

4. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Uptown - Upper Duval, 1.4 km from Midtown
United States
Jiovanni
$152
$239 total
includes taxes & fees
Oct 26 - Oct 27
The Reach Key West, Curio Collection by Hilton
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A beach with palm trees, lounge chairs, and umbrellas.
A tall palm tree with a white building in the background.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

5. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort, 1.6 km from Midtown
United States
Denise
$152
$228 total
includes taxes & fees
Oct 29 - Oct 30
Parrot Key Hotel & Villas
A swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A modern living room with a sectional sofa, a small round table, and a potted plant.

6. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town, 3.5 km from Midtown
United States
Mayra
$106
$147 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Garden Inn Key West / The Keys Collection
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

7. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
3.4 km from Midtown
United States
Stephen
$119
$168 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A deck with sun loungers and a railing overlooking the sea.
A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

8. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Uptown - Upper Duval, 1.5 km from Midtown
United States
Arlene Catherine
$160
$253 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost Beach Resort and Guesthouses
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

9. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort, 2 km from Midtown
United States
Md Y
$174
$196 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
A row of blue bicycles parked under a tree, with a white fence and a building in the background.

10. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 0.9 km from Midtown
United States
Phil
$174
$221 total
includes taxes & fees
Oct 27 - Oct 28
The Grand Guesthouse
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

11. Eden House

Eden House
Historic Seaport, 1.5 km from Midtown
United States
Thomas J
$142
$179 total
includes taxes & fees
Oct 28 - Oct 29
Eden House
An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".
A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.
A white decorative sculpture in a garden area with a white fence and a building in the background.
A motel with a porch, white chairs, and a signboard.

12. Southwinds Motel

Southwinds Motel
Uptown - Upper Duval, 1.4 km from Midtown
United States
Anthony
$139
$190 total
includes taxes & fees
Oct 26 - Oct 27
Southwinds Motel
A building with a white exterior, a large red awning, and a gated entrance.
A pool area with lounge chairs and a lifebuoy.
A spacious kitchen with a dining area, large windows, and a view of the outdoors.
A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

13. Authors of Key West Guest House

Authors of Key West Guest House
The Meadows, 1 km from Midtown
United States
Bryan
$169
$190 total
includes taxes & fees
Oct 27 - Oct 28
Authors of Key West Guest House
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A modern office space with a reception desk, computer, and seating area.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

14. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town, 3.5 km from Midtown
United States
yung
$134
$179 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.
An outdoor patio with tables and chairs, surrounded by trees and a house.
A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.
A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.

15. The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only
Uptown - Upper Duval, 1.5 km from Midtown
United States
David
$149
$213 total
includes taxes & fees
Oct 25 - Oct 26
The Southernmost Inn - Adults Only
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a poolside view.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A hotel room with a balcony, a bed, a desk, and two chairs.

16. Hampton Inn Key West FL

Hampton Inn Key West FL
3.4 km from Midtown
Australia
Ran
$169
$190 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.
A hotel with a white facade, multiple balconies, and lush tropical landscaping.
A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.
A row of bicycles parked in front of a building with a white balcony and a palm tree.

17. The Palms Hotel

The Palms Hotel
The Meadows, 1 km from Midtown
United States
Heather
$178
$223 total
includes taxes & fees
Oct 25 - Oct 26
The Palms Hotel
Pool
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

18. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town, 3.4 km from Midtown
United States
Michele
$125
$197 total
includes taxes & fees
Oct 25 - Oct 26
Blue Flamingo Resort Key West
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A covered outdoor area with a pool, palm trees, and lounge chairs.
A tropical setting with palm trees and a building with a white facade and dark roof.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

19. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 2 km from Midtown
United States
Caleb
$188
$275 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.
A multi-story hotel with balconies and a well-lit entrance.
A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.
A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

20. The Laureate Key West

The Laureate Key West
New Town, 3 km from Midtown
United States
Polly
$159
$207 total
includes taxes & fees
Oct 18 - Oct 19
The Laureate Key West
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Our prices for hotels in Key West are cheapest in September
Price trends for hotels in Key West
Pricing is based on two traveler single night rates
View properties in October
Typical weather for Key West
October
High 28°C / low 27°C. Sunny most days.
View properties in October
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Check out reviews of Midtown hotels guests love

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"We enjoyed the King Suite. Especially the modern updated ensuite. The pool and hot tub were fantastic in a unique private setting with ample palm trees and greenery."
Camiel 3-night trip
Posted 2 hours ago
The Southernmost Inn - Adults Only
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Amazing stay! Would highly recommend!"
Courtney 1-night trip
Posted 4 hours ago
Winslow's Bungalows - Key West Historic Inns
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent
"Unable to understand with the staff on my arrival. It was so frustrating!! Other than that nice atmosphere."
Brigida 2-night trip
Posted 4 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Thank you for an amazing experience and stay! It was so clean and peaceful everywhere on the resort. See you again soon!"
Michael 5-night trip
Posted 6 hours ago
Southernmost Beach Resort and Guesthouses
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Pretty spot with shuttle service to town. Pools are nice, but no beach access. Restaurant was being remodeled, and a food truck was on-site all day with breakfast and lunch or light dinner options. Super friendly and helpful staff!"
Judy 5-night trip
Posted 8 hours ago
Parrot Key Hotel & Villas
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."
Rebecca 3-night trip
Posted 8 hours ago
Beachside Resort & Residences
Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"The location of the property was great for our visit because we had a couple of excursions from the pier not too far. The property was really nice and we enjoyed having the beach to be able to get in the ocean after a hot day. Food and drinks at the hotel were great. The only complaint I have is in our room there was only 1 tabletop lamp and only one in the sitting area so it was real hard to see when trying to get ready with 4 people. Even the bathroom light wasn’t very bright. I would stay here again."
Robin 4-night trip
Posted 9 hours ago
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Great property"
Charlene 3-night trip
Posted 10 hours ago
Casa Marina Key West, Curio Collection by Hilton
Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"It is such a convenient location and beautiful place to stay. Beds are comfy! Wish they had a little more to offer on their menu though."
Amy 3-night trip
Posted 10 hours ago
Margaritaville Beach House Key West
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