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 326 properties available
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). This 2-bedroom, 2 bath condo has been very well maintained with new flooring throughout, freshly u
Emerald Isle 204
Condo -
$145 - $423 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (98)
Top reasons to Book: • All the Amenities-Beachfront heated pool and hot tub, onsite shuffleboard and shared BBQ grills! • Take in unforgettable beachfront views and warm sunshine from your private balcony. • Very close proximity to several top-rated restaurants St Pete Beach has to offer. This 2-bedroom, 2 bath top floor condo at The Caprice has
Caprice 501
Condo -
$203 - $710 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (124)
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 -
$176 - $504 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths / 1 half baths
Guests 6 guests
Rating 5 (4)
Top Reasons to Book:• Unobstructed view of the gulf from the private balcony• Beach access directly across the street (with crossing light for safety!) About 200 steps to the sand!• Onsite Gym for use• 2-minute walk to the beginning of John's Pass (and Bamboo Beach Bar!), with many restaurants and shops• Free WiFi, outdoor pool and hot tub with a b
Madeira Bay Resort I 1504
Condo - Pet Friendly
$124 - $412 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (28)
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 5B - Premier
Condo -
$181 - $706 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (146)
Top reasons to Book: • Beach access is a short distance from the property, just across the street for your convenience. • Property includes an on-site pool (heated seasonally) • Also on the property is a private fishing dock with a cleaning station! This bright and tastefully decorated Townhome is located at well maintained Sea Shell in the quai
Sea Shell 24
House -
$141 - $404 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths / 1 half baths
Guests 6 guests
Rating 4.9 (19)
Top reasons to Book: • Private and beautifully furnished balcony overlooking the Gulf of Mexico! • Unit includes free Wi-Fi and free parking! • Beautifully decorated throughout to reflect coastal comfort. The 5th floor condo at Arena De Madeira features many great updates and is tastefully decorated! This large 3 bedroom condo has a terrific view
Arena De Madeira 502- Premier
Condo -
$212 - $575 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (17)
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 -
$150 - $574 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (53)
Top Reasons to Book: • All the property amenities- Outdoor heated pool, shuffleboard, tiki huts, a shared grilling area, bike racks and complementary in unit Wi-Fi.• You are not limited to one bedroom! This unit includes a queen size sleeper sofa for additional sleeping arrangements.• Located within walking distance to the sugary white sands of St
Friendly Native 507
Condo -
$100 - $294 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (17)
Top Reasons to book:• 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.• Luxury furnishings, with all the co
Oceana 301 East
Condo - Pet Friendly
$124 - $497 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (19)
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 -
$137 - $556 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (42)
Top Reasons to Book: • Spacious screened balcony with brand new outdoor furniture 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. Dreaming of a much needed ge
Villa Madeira 402 - Premier
Condo -
$180 - $667 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (9)

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