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.
330 properties available
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. Comfortable, over-stuffed wicker furniture welcome you to this beach f
Villa Madeira 404 - Premier
Condo -
$235 - $555 / per night
3
bedrooms
2
baths
6
guests
5
(118)
Top reasons to Book:• Beautifully decorated throughout to reflect coastal comfort.• All the Amenities- Beachfront heated pool, hot tub, shared BBQ Area, Free Wi-Fi and onsite laundry facilities. • Located just one mile South is the well-known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment!Sea Breeze is the
Sea Breeze 106
Condo -
$161 - $511 / per night
2
bedrooms
2
baths
6
guests
4.2
(7)
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 Are you drea
Sunset Vistas 411N
Condo -
$202 - $612 / per night
2
bedrooms
2
baths
6
guests
5
(32)
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 2
Condo -
$192 - $560 / per night
2
bedrooms
2
baths
5
guests
5
(101)
Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and a panoramic view of the Gulf of Mexico. • Enjoy direct beach access as well as an outdoor heated pool! • Open floor plan with plenty of room for the entire family to
Trillium 4C - Premier
Condo -
$234 - $583 / per night
2
bedrooms
2
baths
4
guests
5
(90)
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 - Full property - 4 Bedroom
House -
$483 - $1,481 / per night
4
bedrooms
4
baths
15
guests
5
(1)
Top Reasons to book this Beautiful Waterfront unit • Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bayfront. • Watch stunning sunsets from the gulf front, seventh floor “Sunset Roof Top Deck”. • Double amenities, pools and spas, provided by two buildings with the view of your choosing. • New luxury
Oceana 204 East
Condo -
$164 - $479 / per night
2
bedrooms
2
baths
6
guests
5
(31)
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 3-202 Bay Front
Condo -
$162 - $455 / per night
2
bedrooms
2
baths
4
guests
5
(54)
Top reasons to book: • Direct panoramic beachfront views from your large private balcony. • Onsite outdoor amenities in paradise include a beautiful, heated pool, tiki huts, BBQ Grills, a picnic area for dining and relaxing beachside. • Free Wi-Fi, an in unit washer and dryer, and direct beach access for your convenience. Bright and spacious 3-be
Las Brisas 202
Condo -
$246 - $743 / per night
3
bedrooms
2
baths
8
guests
4.9
(67)
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 7-406 Beach Front
Condo -
$163 - $510 / per night
2
bedrooms
2
baths
4
guests
4.9
(71)
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 -
$217 - $527 / per night
3
bedrooms
2
baths
6
guests
5
(89)
Top Reasons to book this Beautiful Beachfront unit • Bring your Fur-baby along! • Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bayfront. • Watch stunning sunsets from the gulf front, seventh floor “Sunset Roof Top Deck”. • Double amenities provided by two buildings with the view of your choosing. •
Oceana 202 West
Condo -
$266 - $601 / per night
2
bedrooms
2
baths
6
guests
5
(48)