Annual and Long Term Rentals

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 334 properties available
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 -
$112 - $308 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (8)
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 6-203 Beach Front
Condo -
$163 - $482 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (39)
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 -
$176 - $516 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (63)
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 -
$150 - $517 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (84)
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. This condo has a large, screened in balcony facing the beach and the G
Villa Madeira 206
Condo -
$195 - $483 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (89)
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 10 - Butterfly 1BR Suite
Condo -
$136 - $293 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
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 02 - Hibiscus 1BR Suite
Condo -
$136 - $293 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 3 guests
Rating 5 (5)
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 3
Condo -
$143 - $457 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (17)
Top reasons to Book: • Free wifi and Free Parking onsite! • Walk to Caddy’s, a beach bar restaurant offering great food, cold drinks and live entertainment! • Shared outdoor beachfront swimming pool! This condo is located in the popular Sunset Beach neighborhood of Treasure Island right on the beach. It has 1-bedroom, 1-bath and was completely re
Sunset Chateau 207
Condo -
$103 - $315 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (22)
Top Reasons to Book: •Admire incredible sunsets on the private, screened-in balcony, which is also great for outdoor dining! •Arie Dam offers wonderful amenities such as a heated pool and spa. •The location is great too! Close to popular John's Pass which offers a variety of restaurants, entertainment, and unique shopping. Lovely and spacious 2 b
Arie Dam 304
Condo -
$246 - $535 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (177)
Top Reasons to Book this Gorgeous Condo:* Beach Access Located Across the Street* Newly Renovated, Ground Floor Unit* All the Amenities: Well Maintained, Seasonally Heated Pool + Large Sundeck* BBQ and Picnic Area for Outdoor Dining Onsite • Boat Friendly Property! (Please inquire for available dock rentals) • Located just a few miles South from th
Barefoot On The Shores II
Condo -
$149 - $293 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (11)
Top Reasons to Book: • Beach access directly across the street as well as on site fishing and charter boats.• Onsite Gym for use • Short stroll away from many shops and restaurants. • Property includes free WiFi and a shared outdoor pool with a beautiful sundeck. • Boat slips available on site at the marina! The Madeira Bay Resort is one of the n
Madeira Bay Resort I 1505
Condo -
$148 - $441 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (67)

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