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

[Florida Keys Travel Guide](https://expedia.ca/Florida-Keys.dx6023765)[Hotels in Florida Keys](https://expedia.ca/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[Vacation Rentals in Florida Keys](https://expedia.ca/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[Flights to Florida Keys](https://expedia.ca/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[Things to do in Florida Keys](https://expedia.ca/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities)[Florida Keys Car Rentals](https://expedia.ca/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[Florida Keys Vacation Packages](https://expedia.ca/Florida-Keys.d6023765.Destination-Travel-Guides)

![Higgs Beach which includes a beach and tropical scenes as well as a large group of people](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Florida Keys Hotels with a Pool

Tonight

[Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Florida Keys hotels with a pool

![Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/55bf0b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/2d5dd8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 outdoor pools, open 7:30 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/ca18911f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/9e920762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lime Tree Bay Resort

[](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

Long Key

9.2/10

Wonderful

(1,137 reviews)

"Beautiful resort on the beach and everything was perfect ."

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

Vinatha

CA $193

CA $280 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/3197fca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Beach Resort

[](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

Matecumbe

9.2/10

Wonderful

(1,634 reviews)

"Great staff, clean room, nice breakfast and convenient location. Enjoyed our week."

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

Warren

CA $263

CA $373 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/9bcc8c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Cottage, Bay View | Terrace/patio](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/0c81ecd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/00031550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/ec70fa51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rock Reef Resort

[](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information)

Rock Harbor

9.2/10

Wonderful

(1,077 reviews)

"Would stay here again!"

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

James

CA $198

CA $223 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/43f0ebf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Room | Water view](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/a4ce58d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/0412cdfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/9f930ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bahia Bay Resort

[](https://www.expedia.ca/Key-Largo-Hotels-Bahia-Bay-Resort.h53826692.Hotel-Information)

Rock Harbor

8.8/10

Excellent

(130 reviews)

"Friendly, communicative and helpful staff. Clean and organized and peaceful. No jets but relaxing hot tub and lovely view of ocean. "

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

Andrew

CA $209

CA $236 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-Largo-Hotels-Bahia-Bay-Resort.h53826692.Hotel-Information)

![Villa, 3 Bedrooms, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2869800/2869762/02af7a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/3000000/2870000/2869800/2869762/bdaf27b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, 3 Bedrooms, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2869800/2869762/484bfa02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![32-inch TV with cable channels](https://images.trvl-media.com/lodging/3000000/2870000/2869800/2869762/4a8993f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glunz Ocean Beach Hotel & Resort

[](https://www.expedia.ca/Key-Colony-Beach-Hotels-Glunz-Ocean-Beach-Hotel-Resort.h2869762.Hotel-Information)

Key Colony Beach

9.0/10

Wonderful

(1,002 reviews)

"Just a great place to stay. Helpful staff and great beach area"

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

Michael

CA $271

CA $365 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-Colony-Beach-Hotels-Glunz-Ocean-Beach-Hotel-Resort.h2869762.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/de0ac7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/e2f3e092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/a088bfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio Suite | Balcony](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/5d36f90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterside Suites & Marina

[](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

Key Largo

9.0/10

Wonderful

(1,184 reviews)

"We just needed a short stay this time, but everything was wonderful. "

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

Thomas

CA $197

CA $261 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1190000/1181000/1180935/9e37e284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Studio Suite, 2 Queen Beds, Kitchen, Canal View](https://images.trvl-media.com/lodging/2000000/1190000/1181000/1180935/d3616ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1190000/1181000/1180935/ddf5edfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1190000/1181000/1180935/6fa6cb57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coconut Cay Resort & Marina

[](https://www.expedia.ca/Marathon-Hotels-Coconut-Cay-Resort-Marina.h1180935.Hotel-Information)

Marathon

8.4/10

Very good

(1,001 reviews)

"Really enjoyed this place "

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

William L

CA $183

CA $206 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Marathon-Hotels-Coconut-Cay-Resort-Marina.h1180935.Hotel-Information)

![Outdoor pool, open 7:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3864000/3863945/7453abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3870000/3864000/3863945/9e96c1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, pool views ](https://images.trvl-media.com/lodging/4000000/3870000/3864000/3863945/4968880a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, pool views ](https://images.trvl-media.com/lodging/4000000/3870000/3864000/3863945/d4b7beed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rainbow Bend Resort

[](https://www.expedia.ca/Marathon-Hotels-Rainbow-Bend-Resort.h3863945.Hotel-Information)

Marathon

8.2/10

Very good

(811 reviews)

"Very convenient location for exploring the Florida Keys. The room and grounds were exceptionally clean and private. Staff were extremely helpful and friendly."

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

Tyson

CA $191

CA $278 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Marathon-Hotels-Rainbow-Bend-Resort.h3863945.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/193fd781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/c05305d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/2e590cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/19311fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Marina Del Mar Resort and Marina

[](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

Key Largo

8.4/10

Very good

(1,679 reviews)

"Wonderful place to stay!"

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

Tempie

CA $164

CA $224 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/be42f21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/2493913c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e12ff0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/15dc33fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amoray Dive Resort

[](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.Hotel-Information)

Key Largo

9.2/10

Wonderful

(1,003 reviews)

"We liked the location right on the water."

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

Laura

CA $171

CA $231 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.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=2026-01-28&endDate=2026-01-29&regionId=6023765&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Florida Keys Hotel Reviews

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"The check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay "

[](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"All the staff were friendly and helpful, and the property was clean and enjoyable! We truly enjoyed our stay! "

[](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent

"We had a wonderfull time. Everyone was very attentive and helpful."

[](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg)

### Hawks Cay Resort

10/10 Excellent

"Overall great experience."

[](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information)

![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg)

### Bayside Inn Key Largo

10/10 Excellent

"Spotless rooms, staff is so friendly and helpful! Amazing place to stay."

[](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back "

[](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Holiday Inn Key Largo by IHG](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg)

### Holiday Inn Key Largo by IHG

10/10 Excellent

"The pool and Tiki bar were nice. "

[](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information)

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Friendly staff, clean rooms, not far from highway, right on canal, just need to be able to handle stairs to get to upstairs bedroom/shower"

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg)

### Cheeca Lodge & Spa

10/10 Excellent

"The property is spectacular - absolutely beautiful, lit up at night with torches and lighting. The room was well appointed, clean and relaxing. The food was good, the service was excellent."

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

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