The Best Cow Key Hotels with Pools from $147 - Hotels with indoor pools in Cow Key, FL

A sunset over a beach with a wooden pier and a small structure on it.

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Our top choices for Cow Key hotels with a pool

Outdoor pool, pool umbrellas, sun loungers

Room, 2 Queen Beds, Bathtub, Ocean View | Living area | 42-inch LCD TV with cable channels, TV

Studio Suite, 1 King Bed with Sofa bed, Bathtub, Partial Ocean View | Premium bedding, pillowtop beds, in-room safe, desk

1. Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

$134 nightly

$151 total

Sep 22 - Sep 23

Total with taxes and fees

Ocean View 3BR Condo with Rooftop Balcony | Balcony

2. Beachside Resort & Residences

Key West

Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.

$185 nightly

$208 total

Sep 20 - Sep 21

Total with taxes and fees

6 outdoor pools, free cabanas, pool umbrellas

Egyptian cotton sheets, premium bedding, down comforters, in-room safe

3. Hilton Key West Resort & Marina

Stock Island

Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.

$159 nightly

$179 total

Sep 28 - Sep 29

Total with taxes and fees

Outdoor pool, open 7:00 AM to 9:00 PM, cabanas (surcharge), sun loungers

4. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.

$133 nightly

$150 total

Sep 27 - Sep 28

Total with taxes and fees

Grand Suite | Premium bedding, pillowtop beds, in-room safe, desk

5. The Perry Hotel & Marina Key West

Stock Island

Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.

$168 nightly

$189 total

Sep 20 - Sep 21

Total with taxes and fees

Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)

6. Hilton Garden Inn Key West / The Keys Collection

New Town

Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.

$130 nightly

$147 total

Oct 4 - Oct 5

Total with taxes and fees

42-inch LCD TV with cable channels, TV, foosball

7. Blue Flamingo Resort Key West

New Town

Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.

$160 nightly

$180 total

Sep 20 - Sep 21

Total with taxes and fees

8. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.

$200 nightly

$225 total

Oct 4 - Oct 5

Total with taxes and fees

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Choose what matters most at hotels with a pool in Cow Key

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Cow Key Hotel Reviews

Beachside Resort & Residences

8/10 Good

"The staff was very helpful. I had absolutely no problem with my suite. It was a very well furnished, one bedroom apartment. The the problem I guess, would be that the outside hot tub at the pool had not been working for months. The elevators were being repaired on the side where I was at the restaurant there. To me was overpriced, and not a lot to choose from. The outside bar, the staff really didn't either know how to make certain drinks, or they didn't have the ingredients to make certain drinks. And the food was so so they only had one Van. That brought you to and from downtown. And they stated that they had 2 more vans, but they've been broke for a very long time, because they can't get parts. Well, how about management getting involved? And going as high up as it takes to get the type of vans that you need and to get the place maintained and staffed properly. There was no pool person, and you had to go inside to get your towels, and it got a little messy at the pool area...And then I heard that there's some people that did have some issues with a room, but those problems were fixed within a day. So, I had wished that the Van would have offered rides to the airport, which was just a 12 minute ride down the street. If that.... the extra excursions they offered did not work out because they didn't have enough people to go on the boat they had. So you had to seek out other sailboats or boats in the area to do things. And if they were no"

Blue Flamingo Resort Key West

10/10 Excellent

"Excellent relaxing destination"

Hampton Inn Key West FL

10/10 Excellent

"Clean room great staff"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"This is the second year we have stayed here for our annual girl's trip. Everything was as great as it was last year. We plan on staying again next year."

Southwinds Motel

10/10 Excellent

"Second time staying at this hotel and will be back ASAP"

Ibis Bay Beach Resort

10/10 Excellent

"Had a great time here."

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Our stay was pleasant except for the rooster in the Palm tree that woke me up at 3;45 AM in the morning."

The Perry Hotel & Marina Key West

10/10 Excellent

"Loved it, marina view room"

Frequently asked questions

What are some hotels with pools in Cow Key?

Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. Blue Flamingo Resort Key West: Hotel located near Florida Keys Beaches. Offers 2 restaurants, 2 outdoor pools, and 2 pool bars. Margaritaville Beach House Key West: Hotel, 13-minute walk from Florida Keys Beaches. Provides a 24-hour fitness center, an outdoor pool, and televisions. Ibis Bay Beach Resort: Hotel located near Florida Keys Beaches. Features a private beach, an outdoor pool, and daily. Havana Cabana at Key West: Hotel located near Florida Keys Beaches. Offers a snack bar/deli, an outdoor pool, and free self parking.

What is there to see and do in Cow Key?

Explore places like Duval Street and Florida Keys Beaches while you're in the area. Make a point to visit attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.

When is the best time to book a hotel with a pool in Cow Key?

Taking into account the local weather in Cow Key can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Cow Key is 38 inches.

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Lodging

Room 1

Check availability on Cow Key Hotels with a Pool

Our top choices for Cow Key hotels with a pool

1. Hampton Inn Key West FL

2. Beachside Resort & Residences

3. Hilton Key West Resort & Marina

4. DoubleTree Resort by Hilton Grand Key - Key West

5. The Perry Hotel & Marina Key West

6. Hilton Garden Inn Key West / The Keys Collection

7. Blue Flamingo Resort Key West

8. Hyatt Vacation Club at Windward Pointe, Key West

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

10. Hyatt Vacation Club at Beach House, Key West

Choose what matters most at hotels with a pool in Cow Key

Top Cow Key Hotel Reviews

Beachside Resort & Residences

Blue Flamingo Resort Key West

Hampton Inn Key West FL

Hyatt Vacation Club at Windward Pointe, Key West

Southwinds Motel

Ibis Bay Beach Resort

Hilton Garden Inn Key West / The Keys Collection

The Perry Hotel & Marina Key West

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Cow Key, FL

Check availability on Cow Key Hotels with a Pool

Our top choices for Cow Key hotels with a pool

1. Hampton Inn Key West FL

2. Beachside Resort & Residences

3. Hilton Key West Resort & Marina

4. DoubleTree Resort by Hilton Grand Key - Key West

5. The Perry Hotel & Marina Key West

6. Hilton Garden Inn Key West / The Keys Collection

7. Blue Flamingo Resort Key West

8. Hyatt Vacation Club at Windward Pointe, Key West

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

10. Hyatt Vacation Club at Beach House, Key West

Choose what matters most at hotels with a pool in Cow Key

Top Cow Key Hotel Reviews

Beachside Resort & Residences

Blue Flamingo Resort Key West

Hampton Inn Key West FL

Hyatt Vacation Club at Windward Pointe, Key West

Southwinds Motel

Ibis Bay Beach Resort

Hilton Garden Inn Key West / The Keys Collection

The Perry Hotel & Marina Key West

Frequently asked questions

Explore a world of travel with Expedia