Poolside Properties

During the winter and summer season, most properties require a Saturday check-in/check-out date. If your dates are flexible and the search result doesn't return a property that meets your requirements, please adjust your dates accordingly or call our Guest Services Team at 727-363-3336.

Properties Available 326 properties available
Top Reasons to Book:* 173 Yards to the Gulfport Beach Recreation Area* 5 Miles to St. Pete Beach* Pet Friendly up to 20lbs. (Additional Cost Applies) * On-Site Parking and Laundry Facility * Walking Distance to many Restaurants, Art Galleries, and Boutiques* Professionally Managed * Gas Grill on grounds* Hulu Live access!Beach Quarters 3BR is a com
Beach Quarters 3BR - #2, #3, #4
Condo Pet Friendly
$230 - $775 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 12 guests
Top Reasons to Book this Condo: * Top Floor Corner Unit with Bay Views * Onsite heated pool* All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts.* Boardwalk that wraps around the community for your morning exercise or evening stroll.* Located on the penins
Land's End 3-406 Bay Front
Condo -
$123 - $466 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (35)
Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts. • Boardwalk that wraps around the community for your morning exercise or evening stroll. • Located on the peninsula, this community o
Land's End 7-401 Beach Front - Premier
Condo -
$144 - $582 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (84)
Top reasons to book: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all the action and entertainment! The Sand Dunes Townhome has many interior upgrades with every possible amenity you could desire and beautiful new flooring throughout. The open liv
Sand Dunes Townhome C1
House -
$192 - $690 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (28)
Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts. • Boardwalk that wraps around the community for your morning exercise or evening stroll. • Located on the peninsula, this community o
Land's End 10-203 Beach Front - Premier
Condo -
$148 - $577 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (64)
Top Reasons to Book: • Take in unforgettable panoramic beachfront views and warm sunshine from your private balcony. • Short drive to St Petersburg- loaded with great museums, shops and restaurants. • Shared outdoor pool on site (heated seasonally). Inside this stunning 4th floor condo, you’ll find the open floorplan, coastal décor, and comfortable
Emerald Isle 403 - Premier
Condo -
$227 - $660 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (14)
Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts. • Boardwalk that wraps around the community for your morning exercise or evening stroll. • Located on the peninsula, this community o
Land's End 10-201 Beach Front - Premier
Condo -
$148 - $577 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (130)
Top reasons to Book: • A beautiful, shared beachfront pool. • beautifully furnished patio and balcony overlooking the Gulf of Mexico! • The location- directly on Sunset beach and a short distance to several well-known restaurants and live entertainment.• Dog friendly! 50lb/dog limit. 2 dogs max. (Fees and restrictions apply) "Serenity By The Se
Serenity By The Sea - Beach House
House - Pet Friendly
$386 - $1,208 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half baths
Guests 8 guests
Rating 4.9 (118)
Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts. • Boardwalk that wraps around the community for your morning exercise or evening stroll. • Located on the peninsula, this community o
Land's End 8-306 Beach Front - Premier
Condo -
$150 - $574 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (53)
Top reasons to Book: • All the Amenities-THREE luxurious swimming pools, hot tubs, an outdoor grilling area, fitness center, and beach access. • Direct panoramic views from your private balcony. • 10 minutes on the beach trolley to the well-known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment! Beautiful
Tides 2-423
Condo -
$145 - $480 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)
Top reasons to book: • All the amenities-Outdoor pool (heated seasonally), Free WiFi, In unit washer and dryer, easy beach access directly across the street. • Unit includes 2 kayaks, 4 bicycles and a one car garage. • Located just a few miles South is the well known John’s Pass Village which is loaded with tons of shopping, restaurants, and entert
Mariner's Pointe 202
Condo -
$133 - $436 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (70)
Top Reasons to Book:• Direct Beach Front with Gulf Views from Multiple Balconies• Large Outdoor Covered Terrace perfect for Relaxing and Soaking in the Sunsets• Additional Patio Space Perfect for Grilling and Sunbathing• Pet Friendly (2 small dogs or 1 large dog, Additional Fees Apply)• Lower-Level Game Room with Pool Table and Foosball Table• Elev
Seaclusion Beach Townhome
House - Pet Friendly
$603 - $1,931 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half baths
Guests 12 guests
Rating 4.9 (49)

Tell us what you're looking for and someone will contact you with available options.

I agree