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 331 properties available
Top Reasons to Book: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs & access to the heated saltwater swimming pool during your visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. The minute you walk in, you'll feel right at home at this bright con
Villa Madeira 406
Condo -
$218 - $518 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (38)
Top Reasons to Book: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated saltwater swimming pool during your visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. Welcome to paradise!! This lovely maintained 2 bedroom + den, 2 bath c
Villa Madeira 307 - Premier
Condo -
$234 - $546 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (58)
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). Nicely updated 2-bedroom, 2 bath condo located on the South corner of the building with direct v
Emerald Isle 101
Condo -
$160 - $457 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (77)
The Original “Salt Water Suites” is a meticulously maintained property in the heart of North Redington Beach. The owners of the property have furnished and decorated these adorable, one of a kind 1BR and Studio Suites with so much love and attention to detail.We represent all 12 Suites. Please ask us for additional information if you need to accomm
Salt Water Suites 06 - Seaside 1BR Suite
Condo -
$135 - $288 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (7)
Welcome to Upham Beach Inn, a meticulously maintained property situated in the heart of St. Pete Beach! Our 12 charming Suites are thoughtfully furnished and adorned with tasteful decor, ensuring a comfortable and delightful stay.We take pride in representing all 12 Suites and are more than happy to provide additional information for larger groups
Upham Beach Inn - #3 Studio
Apartment -
$91 - $251 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 3 guests
Rating 5 (3)
Top Reasons to Book: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. Beautifully updated and remodeled beach front condo at Villa Madeira. The décor
Villa Madeira 202
Condo -
$218 - $518 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (137)
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). If you are looking for a beautifully updated, cozy beachfront condo – look no further because you
Emerald Isle 104
Condo -
$160 - $457 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (63)
Top reasons to book: • Best of Both Worlds – Beach and -Outdoor pool (heated seasonally), Free Spectrum WiFi and Cable, In unit washer and dryer, easy beach access directly across the street.• Unit includes a two-car tandem garage loaded with a propane grill 4 kayaks, Paddleboard, 2 bicycles, beach chairs and plenty of beach gear!• Location,
Mariner's Pointe 701
Condo -
$171 - $495 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (28)
Located on the #1 rated Sunset Beach, The Sunset Beach House is a totally unique, oceanfront oasis. Resting on 100 feet of private coastline, every residence features lanais and balconies overlooking historic Sunset Beach. In October 2020, the entire property was renovated and reimagined as Treasure Island’s only truly boutique experience. New sand
Sunset Beach House - Beach Hugger 1
Condo -
$160 - $460 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (20)
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 4-201 Bay Front
Condo -
$161 - $446 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (34)
This recently updated 2 bedroom, 2 bath beachfront condo at Land's End has amazing Gulf views from your living room, master bedroom and of course your private balcony! The beautiful, fully stocked kitchen has been done with granite counter tops, both master and guest bathrooms have been updated and look lovely, newer flooring throughout, updated fu
Land's End 9-403 Beach Front - Premier
Condo -
$171 - $570 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (49)
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 11-407 Beach Front - Premier
Condo -
$190 - $567 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (63)

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