Title: Book the Best Hotels with POOL in Midtown in 2026 | Expedia.ca

[Midtown Travel Guide](https://expedia.ca/Key-West-Midtown.dx553248635976480489)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Midtown Car Rentals](https://expedia.ca/Car-Rentals-In-Midtown.d553248635976480489.Car-Rental-Guide)[Midtown Vacations](https://expedia.ca/Midtown.d553248635976480489.Destination-Travel-Guides)

![The sign says it all.](https://images.trvl-media.com/place/1187/193153ec-9280-4785-aba4-30c50138d70b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Ronald Wilson

# Find Hotels with a Pool in Midtown, FL from CA $153

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## Check availability on Midtown Hotels with a Pool

Tonight

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Midtown hotels with a pool

![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Loaf Lodge

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information)

Summerland Key

8.2/10

Very good

(1004)

"Great place to stary. Staff was very nice."

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

norka

CA $136

CA $153 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information)

![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![49-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/4777ebf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/8475e5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/948eecb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Perry Hotel & Marina Key West

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

Stock Island

9.4/10

Exceptional

(1173)

"great place to stay "

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

michael

CA $179

CA $284 total

includes taxes & fees

Dec 17 - Dec 18

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

![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/dcdeb665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/5792173a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Flamingo Resort Key West

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

New Town

8.0/10

Very good

(1772)

"Great, friendly staff, nice amenities, easy parking and convenient location "

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

Caitlyn

CA $172

CA $271 total

includes taxes & fees

Dec 17 - Dec 18

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

![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily continental breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/3484f3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/ee750f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Key West / The Keys Collection

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

New Town

8.0/10

Very good

(1157)

"clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel."

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

Shanker

CA $178

CA $239 total

includes taxes & fees

Dec 17 - Dec 18

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

![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/4233d834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/62b1909b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/2ac07b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5710a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Margaritaville Beach House Key West

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

Key West

8.8/10

Excellent

(1779)

" Great location "

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

Kristen

CA $357

CA $489 total

includes taxes & fees

Dec 17 - Dec 18

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NYAH Key West - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information)

Key West Historic District

8.0/10

Very good

(1004)

"Great little hotel in the heart of Old Town."

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

Robert

CA $148

CA $229 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information)

![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/c6252245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/ffbb5429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/e235d199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Key West

8.0/10

Very good

(1007)

"Very very nice stay! "

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

Chloe

CA $212

CA $285 total

includes taxes & fees

Dec 17 - Dec 18

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

![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (Adults Only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/4c7ce9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8ea2dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Duval House

[](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

Old Town Key West

9.4/10

Exceptional

(1010)

"I loved this place the location was absolutely perfect "

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

Frank

CA $164

CA $214 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/17dd6b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, windsurfing, kayaking](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7c8298bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/3691f3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ibis Bay Beach Resort

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information)

Northside Resort

8.2/10

Very good

(2012)

"Good location and breakfast "

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

Abhay

CA $166

CA $224 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information)

![Building design](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/34b65216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed (ADULT ONLY)](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/ee1be58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Southernmost Inn - Adults Only

[](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information)

Old Town Key West

8.2/10

Very good

(1213)

"Great rooms, clean great friendly staff."

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

Ryan

CA $205

CA $293 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.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=2025-12-30&endDate=2025-12-31&regionId=553248635976480489&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Midtown Hotel Reviews

![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

"."

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

"shuttle"

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

"Beach and pool - bar, music and great staff"

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

"Clean room, great amenities, very nice staff and close by foot to restaurants and stores."

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

"clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel."

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

"My husband and I enjoyed our stay at the hotel tremendously - everything was excellent! Location, cleanliness, pool, food, bedding, friendly staff, hotel decor, pleasant ambiance. Highly recommend this hotel to the guests who want to experience upscale services and hospitality of old Florida"

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

"Quaint hotel with beautiful grounds. Close to everything yet far away enough away from Duvall. Clean and comfortable rooms"

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

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

### Beachside Resort & Residences

10/10 Excellent

"The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area "

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

"Beautiful place"

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

## Frequently asked questions

### What are some accommodations with pools in Midtown?

### What is there to see and do in Midtown?

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