Annual and Long Term Rentals

Properties Available 250 properties available
Top reasons to book: • The location-Directly across from John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment!! • All the amenities-outdoor beachfront pool (heated seasonally), a BBQ grilling area, an outdoor dining area, assigned parking & direct beach access! • Beautifully decorated throughout to reflect c
Madeira Norte 304
Condo -
$175 - $450 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (45)
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 - All
House -
$819 - $2,145 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 24 guests
Rating 5 (3)
Top Reasons to Book: • Enjoy The low density and well-maintained beachside complex with beach access. • Very close proximity to many well know restaurants in the area. • Brand new kitchen and balcony furnishings • Beautifully decorated throughout to reflect coastal comfort.Experience many breathtaking sights of the Gulf of Mexico right from your b
Pelican Pointe 2A
House -
$130 - $480 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Top reasons to book: • Comfortable patio furnishings to allow for lounging and relaxing on the large beachfront balcony! • All the amenities-TWO heated beachfront pools, a 250 feet private pier, a BBQ and cabana area, tiki huts and direct beach access! • Located just a few miles South is the well known John’s Pass Village which is loaded with tons
La Contessa 306
Condo -
$150 - $426 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (1)
Top Reasons to Book: • All the Amenities! Large Heated Pool, Kiddie Pool, Hot Tub, Fitness Center, Bicycles, BBQ Grills, Beach Tiki Bar and Café all in one location! • Living room and main bedroom accessible to the private beach balcony. • Located less than one mile South of John's Pass. • In-unit free Wifi Access, Assigned Parking Located on
Sunset Vistas 408N
Condo -
$170 - $555 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Top reasons to Book: • 4 total units for this building, the perfect getaway for the entire family! • TWO balconies per condo, one facing South overlooking the Gulf and one facing North. • Onsite heated pool & direct beach access. Experience true Florida living in this charming beachfront property!! This amazing 2 bedroom, 2 bath condo has an
Sunset Villas 3
Condo -
$165 - $583 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (58)
.Top reasons to book: • Don’t forget your fur baby! This unit is pet friendly (restrictions apply). • 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! Madeira Del Mar is a br
Madeira Del Mar 305
Condo - Pet Friendly
$195 - $580 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (10)
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 9-201 Beach Front - Premier
Condo -
$166 - $528 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5.1 (40)
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 offers
Land's End 11-305 Beach Front - Premier
Condo -
$153 - $517 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
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. Beautifully updated and remodeled beach front condo. The décor is ta
Villa Madeira 203 - Premier
Condo -
$164 - $516 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (49)
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 -
$118 - $427 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (18)
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 10-305 Beach Front
Condo -
$156 - $481 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (22)

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