Gulfport Hotels with Swimming Pool

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Check availability on Gulfport Hotels with Swimming Pools

Our top choices for Gulfport hotels with a pool

2 outdoor pools, pool cabanas (surcharge), pool umbrellas
Barefoot Beach Club

Barefoot Beach Club

Barefoot Beach Club
2.5 star property
Madeira Beach
9.4 out of 10, Exceptional, (1116)
"Everything was great love the place. "
United States
Greg
Barefoot Beach Club
View from room
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound
4.0 star property
Bradenton
9.4 out of 10, Exceptional, (1880)
"Very nice stay; wonderful staff"
United States
Karen
The price is RM625
RM822 total
includes taxes & fees
22 Dec - 23 Dec
Compass Hotel by Margaritaville Anna Maria Sound
Terrace/patio
Avalon Hotel Downtown St. Petersburg

Avalon Hotel Downtown St. Petersburg

Avalon Hotel Downtown St. Petersburg
2.5 star property
Downtown St. Petersburg
9.2 out of 10, Wonderful, (1347)
"The room was quite humid, but other than that it was a great quick stay."
United States
Michelle
Avalon Hotel Downtown St. Petersburg
Outdoor pool
Hollander Boutique Hotel

Hollander Boutique Hotel

Hollander Boutique Hotel
3.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (2176)
"It's in a great location and the staff is super helpful; we would stay here again."
United States
HENRIETTE
Hollander Boutique Hotel
Outdoor pool, pool umbrellas, pool loungers
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (2883)
"Nice resort, clean, friendly staff and plenty of things to eat! "
United States
Danielle
The price is RM901
RM1,180 total
includes taxes & fees
7 Jan - 8 Jan 2026
Wyndham Grand Clearwater Beach
Outdoor pool, pool umbrellas, pool loungers
Cambria Hotel St Petersburg-Madeira Beach Marina

Cambria Hotel St Petersburg-Madeira Beach Marina

Cambria Hotel St Petersburg-Madeira Beach Marina
3.0 star property
Madeira Beach
9.2 out of 10, Wonderful, (1000)
"Food and services were great "
United States
Hilary
The price is RM542
RM613 total
includes taxes & fees
23 Dec - 24 Dec
Cambria Hotel St Petersburg-Madeira Beach Marina
Exterior
Crystal Bay Historic Hotel

Crystal Bay Historic Hotel

Crystal Bay Historic Hotel
3.0 star property
La Vista
9.6 out of 10, Exceptional, (1420)
"Great place to stay, very good breakfast!"
United States
Monika
The price is RM495
RM559 total
includes taxes & fees
18 Dec - 19 Dec
Crystal Bay Historic Hotel
Outdoor pool
Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG
2.5 star property
Downtown Dunedin
9.4 out of 10, Exceptional, (968)
"Very nice staff and clean room …..good location"
United States
Gloria
The price is RM505
RM571 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG
Lobby
Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach
3.0 star property
Clearwater Beach
8.8 out of 10, Excellent, (1001)
"Great location for the price."
United States
Chayamon
The price is RM619
RM699 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Clearwater Beach
Terrace/patio
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront
4.0 star property
Rocky Point
8.2 out of 10, Very good, (1003)
"Staff was fantastic. Won’t stay again due to the high parking fees . Hotel was in great location and great views. "
United States
Christina M
The price is RM502
RM569 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Tampa Rocky Point Waterfront
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.
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Top Gulfport Hotel Reviews

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"Loved everything and Javier in the Front desk was amazing. The Valet boys and Bellboys do an amazing job"
Esperanza 1-night trip
Posted 1 day ago
Wyndham Grand Clearwater Beach

Frequently asked questions

What are some hotels with pools in Gulfport?
Wyndham Grand Clearwater Beach: Hotel, 3-minute walk from St. Petersburg - Clearwater Beaches. Features 3 restaurants, an outdoor pool and a full-service spa. Hilton Clearwater Beach Resort & Spa: Resort, 2-minute walk from St. Petersburg - Clearwater Beaches. Offers a private beach, 2 outdoor swimming pools and 3 restaurants. DoubleTree by Hilton Tampa Rocky Point Waterfront: Hotel, 9-minute walk from Tampa Bay. Provides a snack bar/deli, an outdoor pool and complimentary high-speed (wired) Internet access. Hotel Alba, Tapestry Collection by Hilton: Hotel located near Tampa Bay. Features 2 bars, a pool and a snack bar/deli. Hilton St. Petersburg Bayfront: Hotel, 4-minute walk from Tampa Bay. Offers LCD televisions, a pool and laundry facilities.
What is there to see and do in Gulfport?
Explore places such as Tampa Bay while you're in the area. Enjoy a stroll along the shore at Gulfport Beach. The beaches and restaurants are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Gulfport?
You may want to consider a place to stay with an outdoor pool if you plan to visit St. Petersburg - Clearwater in the driest months of February, November or December, when the average rainfall is 49 mm. Accommodation with an indoor pool may be the way to go if you are visiting during the rainiest months of July, August and June when the average rainfall is 187 mm.