Title: The Best Hotels with a Pool in Dredgers Key from $336 in 2026 | Expedia.com

[Dredgers Key Travel Guide](https://expedia.com/Dredgers-Key.dx180165)[Hotels in Dredgers Key](https://expedia.com/Dredgers-Key-Hotels.d180165.Travel-Guide-Hotels)[Vacation Rentals in Dredgers Key](https://expedia.com/Dredgers-Key-Vacation-Rentals.d180165.Travel-Guide-VacationRentals)[Flights to Dredgers Key](https://expedia.com/Cheap-Flights-To-Dredgers-Key.d180165.Travel-Guide-Flights)[Car Rentals in Dredgers Key](https://expedia.com/Car-Rentals-In-Dredgers-Key.d180165.Car-Rental-Guide)[Dredgers Key Vacation Packages](https://expedia.com/Dredgers-Key.d180165.Destination-Travel-Guides)

![Sailboat Anchored off coast of Dredger Key Sigsbee - Key West Florida](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Dredgers Key Hotels with a Pool

Tonight

[Feb 15 - Feb 16](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-15&endDate=2026-02-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 16 - Feb 17](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-16&endDate=2026-02-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Dredgers Key hotels with a pool

![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/12041d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/fe329a14.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)

![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Loaf Lodge

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

Summerland Key

8.2/10

Very Good

(1,002 reviews)

"Clean, convenient location. "

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

Michael

$299 nightly

$336 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/925121e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/ce4bddc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

[](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(56 reviews)

"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."

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

Raj

$413 nightly

$458 total

Feb 18 - Feb 19

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fa9fff97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fcb4c32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage with swimming pool and dockage, just minutes to Key West!

[](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(166 reviews)

"Everything was there that I needed. Very nice area for my dog."

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

Terry

[](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

![Food and drink](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5fd7b8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/82d7bf8c.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)

### Margaritaville Beach House Key West

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

Key West

8.8/10

Excellent

(1,787 reviews)

"Clean room, amazing food at the resort, and a courteous staff. Thank you for a great stay."

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

michael

$492 nightly

$553 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Water view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/e5a3b3c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/ce510800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 3BR Condo with Rooftop Balcony | Balcony](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/a1e6ec60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Resort & Residences

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

Key West

8.6/10

Excellent

(1,987 reviews)

"Great stay"

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

Timothy

$371 nightly

$418 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Front of property](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2641h1530x1y4-f00b5aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | 4 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2304h1532x8y4-86de2f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2720h1531x0y0-d54bbbc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | Garden view](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w1153h1530x0y2-2909ca24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Atlantic View Luxury Villa with Pool

[](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

Summerland Key

10/10

Exceptional

(1 review)

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

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

Preetam

$975 nightly

$1,097 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/bd916166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7df2a82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront Walkout Suite - King | View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/4caaa3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Old Town Key West

8.4/10

Very Good

(545 reviews)

"Beautiful beach- gorgeous hotel-top level service - love everything about it!"

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

Debbie

$668 nightly

$752 total

Mar 8 - Mar 9

Total with taxes and fees

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

![6 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/0fcf571b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/15e67a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/5714c59c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceans Edge Key West Resort, Hotel & Marina

[](https://www.expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

Stock Island

9.0/10

Wonderful

(1,808 reviews)

"Good location and service"

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

Weiling

$418 nightly

$470 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/53a8339f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room, 2 Double Beds, Bay View | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/1c18f751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7ea6251e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/d05e8fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ibis Bay Beach Resort

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

Northside Resort

8.0/10

Very Good

(2,078 reviews)

"Great ppl that work there! "

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

Evan

$389 nightly

$437 total

Mar 18 - Mar 19

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/dc4f2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cudjoe Cottages, swimming pool, just 20 miles from Key West

[](https://www.expedia.com/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(151 reviews)

"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "

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

bryan c.

$657 nightly

$729 total

Feb 21 - Feb 22

Total with taxes and fees

[](https://www.expedia.com/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.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=2026-03-02&endDate=2026-03-03&regionId=180165&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Choose what matters most at hotels with a pool in Dredgers Key

Breakfast included

4 stars

Ocean view

5 stars

Hot tub

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_180165)

## Top Dredgers Key Hotel Reviews

![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

"Clean room everything was very nice"

[](https://expedia.com/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

"The room was very spacious and offered a lot more amenities for the price such as full kitchen, washer, dryer and great views from balcony. We will be back. "

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

"Our room was perfect and the staff kept checking on us to make sure everything was satisfactory "

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

![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

"Far from the great, maddening crowd of old town, but only a 20 minute, free shuttle ride away...a wonderful relaxing location with a great pool, bar and an additional full service restaurant and bar."

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

"Room was spotless, light airy feel throughout the space. The view out our balcony elevated our entire stay! Attention to details upon arrival, soft music playing on the tv with a personalized welcome greeting. Resort was beautiful and well maintained, their landscaping was eye candy for this Ohio girl. We look forward to our next visit, thanks for the hospitality Oceans Edge!"

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

"Rooms were very clean and well appointed. Front desk staff were welcoming and personable. The welcome champagne was a nice touch. The complimentary shuttle to downtown was a nice perk. Breakfast by the pool was delicious!!"

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

"I am giving this 5 stars only because the way they handled the fact that there was no cold water was by reducing my bill significantly. If they had not handled it well, it would be a one star review."

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

![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg)

### Parrot Key Hotel & Villas

10/10 Excellent

"Room was very clean. Staff was friendly. Food at the bar was good. Only complaint was housekeeping did not show up one day. We came back at 5:00 pm to find an unmade room. The hotel is very pricey. We did expect our room to be cleaned daily. Mgmt said they were short staffed. "

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

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg)

### Ibis Bay Beach Resort

10/10 Excellent

"Great location. Staff was great. Amenities were convenient. Beautiful property, well maintained. Restaurant staff was great. "

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