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 329 properties available
Top reasons to Book: • Covered parking available for two vehicles! • Ocean Kayak for guest use! • A beautiful, heated pool, direct beach access, an outdoor shower and picnic tables are located beachside onsite. • Located just a few miles South is the well-known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainmen
Gulfside Villas 3
House -
$202 - $596 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (40)
Top reasons to Book: • All the Amenities-THREE luxurious swimming pools, hot tubs, an outdoor grilling area, fitness center, and beach access. • Direct panoramic views from your private balcony. • 10 minutes on the beach trolley to the well-known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment! This condo
Tides 4-642
Condo -
$152 - $491 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (9)
Top reasons to book: • Best of both worlds! Gorgeous sunrises from your private balcony, famous sunsets in your back yard• Beautifully updated and furnished!• Onsite amenities include an outdoor heated pool, a community grilling area, private beach access alongside a shower/rinse area.• Located just a few miles South is the well-known John’s P
Promotion available! Promotion available!
Promotion available!
Limited Time Only!

Save for stays between November 2022 and April 2023 by using Promo Code HVWINTER at checkout!
Holiday Villas II 407 Premier
Condo -
$201 - $543 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (23)
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 11-405 Beach Front - Premier
Condo -
$186 - $571 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (109)
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! • One of very few handicapped accessible units! • Living room and main bedroom accessible to the private beach balcony. • Located less than one mile South of John's Pass. • In-unit fr
Sunset Vistas 206S
Condo -
$192 - $551 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths / 1 half baths
Guests 6 guests
Rating 4.9 (46)
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 203 West
Condo - Pet Friendly
$264 - $609 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (53)
**CLOSURE NOTICE** THE POOL AND POOL DECK WILL BE CLOSED FOR MAINTENANCE. SEPTEMBER 1ST, 2023 - MARCH 1ST, 2024Top Reasons to Book: • All the Amenities! Pool, Hot Tub, Sauna, Fishing Docks, Tennis Courts, Shuffleboard and Pickleball, all in one location! • Boat Slips available for easy access as a pick up/ drop off area for your Friends & Fam
Bayshore Yacht & Tennis 314
Condo -
$109 - $380 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (13)
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 9-202 Beach Front
Condo -
$178 - $532 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (84)
Top Reasons to Book:-Less than 400 Feet to the Beach-Pet Friendly (Restrictions and additional fees apply)-Private off-street parking-Recently Updated and New Stainless Steel Appliances-Open Concept with TONS of seating- Huge Patio perfect for loungingDiscover tranquility in our fully furnished 5BR/3BA Cottage, nestled just steps away from the pris
Beach Life 5
House - Pet Friendly
$335 - $1,134 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 14 guests
Rating 5 (1)
Top Reasons to Book Sandy Dunes! • Just steps to the beach! • Spacious Layout, gorgeous furnishings, plenty of room for the entire family! • Additional outdoor seating for gathering dining and relaxation Enjoy a much-deserved beach vacation at this dreamy coastal retreat. This beautiful, family-friendly, beach house features quartz countertops, s
Sandy Dunes
House
$350 - $638 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 - #12 1BR Suite
Apartment
$100 - $331 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Top reasons to Book: • Free wifi; 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 beautifully updated, bright and tastefully decorated condo is located in the popular Sunset Beach neighborhood of Treasure Island right on the bea
Sunset Chateau 511
Condo -
$89 - $322 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 4.8 (14)

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