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 328 properties available
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 -
$153 - $546 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (49)
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 -
$146 - $521 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (24)
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 - #10 1BR Suite
Apartment -
$97 - $315 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (6)
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 -
$154 - $541 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (55)
This condo is located in the popular Sunset Beach neighborhood of Treasure Island right on the beach. This comfortable 2-bedrooms, 2-baths condo has a fully equipped kitchen with all you need to prepare a nice meal, tile flooring in living/kitchen area and tasteful décor. The living area features a large flat screen TV and a very comfortable sectio
Sunset Chateau 603
Condo -
$118 - $460 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (44)
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 1-301 Gulf View - Premier
Condo -
$116 - $471 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 5 (81)
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 of
Land's End 1-203 Pool View
Condo -
$108 - $448 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (48)
Top reasons to Book: • 4 total units for this building, the perfect getaway for the entire family! • TWO balconies per condo, one facing West overlooking the Gulf and one facing East. • Onsite heated pool; direct beach access. Experience true Florida living in this charming beachfront property!! This amazing 2 bedroom, 2 bath condo has an open a
Sunset Villas 4
Condo -
$201 - $606 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (121)
Please note that this is a NON SMOKING PROPERTY!Directly across the street from the beach and completely remodeled at the end of 2022! This super cute house consists of 4 individual 1BR units, each with a kitchen, bedroom, living room and full bathroom. The location is perfect for the single traveler, couples, families or a larger group of friends/
Twin Tiki 2
Condo -
$115 - $296 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (9)
Top Reasons to Book: • Family friendly with tons of onsite amenities • One of very few handicapped accessible units • Living room and main bedroom accessible to the private balcony • Located less than one mile South of John's Pass • In-unit free Wifi Access, Assigned Parking This Sunset Vistas 2-bedroom, 1.5-bathroom condo offers a perfect blend
Sunset Vistas 207S
Condo -
$171 - $524 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths / 1 half baths
Guests 6 guests
Rating 5 (6)
Top reasons to book: • Onsite outdoor resort style pool (heated seasonally) with new pool deck furniture. • Located just 1.5 miles South is the well known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment!• Don’t forget your fur baby! This unit is pet friendly (restrictions and fees apply). Vacation memories
Madeira Del Mar 205
Condo - Pet Friendly
$196 - $647 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (39)
Top Reasons to Book Crystal Palms 302: * 200 Feet to Beach Access * Large Balcony* Perfect for Couples with King and Queen Bedrooms* Heated Pool, Hot Tub * Convenient location close to all the main attractions* Professionally Managed Have the ultimate Florida getaway at this 2-bedroom, 2-bath Treasure Island vacation rental. Located just 200 feet f
Crystal Palms 302
Condo -
$100 - $394 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (7)

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