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 322 properties available
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 -
$110 - $653 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (71)
Top reasons to Book: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary white sands of Madeira Beach. • Plenty of comfortable outdoor furnishings to relax and enjoy the warm Florida sunshine. You will love this charming waterfront home with a fishing dock overlooking Boca Ciega Bay! It's in walking
Coconut Paradise
House -
$110 - $503 / per night
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 8 guests
Rating 4.9 (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 7-306 Beach Front - Premier
Condo -
$125 - $685 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (68)
Top Reasons To Book:• Quick access to the heated pool• Newly updated in January 2024• Boardwalk that wraps around the community for your morning exercise or evening stroll• Top floor unit with wide Intracoastal views• 2 Private balconies to enjoyWelcome to your perfect getaway at Land's End in this newly updated top-floor condo with breathtaking ba
Land's End 1-406 Bay Front - Premier
Condo -
$110 - $531 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (5)
Top reasons to Book: • 4 total units for this building, the perfect getaway for the entire family!• TWO balconies per condo, one facing West overlooking the Gulf and one facing East. • Onsite heated pool; direct beach access. Experience true Florida living in this charming beachfront property!! This amazing 2 bedroom, 2 bath condo has an open an
Sunset Villas 2
Condo -
$173 - $637 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (106)
Top Reasons to Book this Home: * Single Family Home with Private Pool* Screened in Florida Room with Beverage Fridge* Tropical Decor, Spacious Living* Spacious Deck Area around Private Pool with Grill* Convenient to St Pete Beach and Treasure Island* 880yds to Upham Beach* Professionally ManagedWelcome to Coquina Hideaway!! This charming 2-bedroom
Coquina Hideaway
House
$100 - $339 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 7 guests
Top Reasons to Book 202W: * Direct Beachfront Condo in the WEST building with Private Balcony * “Sunset Roof Top Deck” on the 7th Floor for Even MORE Beach Views! * Pool with Deck and Lounge Chairs, Hot Tub on Grounds * Updated and Comfortable Furnishings * Dogs allowed (Fees and Restrictions apply) Escape to paradise in this updated 2-bedroom,
Oceana 202 West
Condo - Pet Friendly
$158 - $662 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (58)
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 7-404 Beach Front - Premier
Condo -
$125 - $685 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (90)
** CONSTRUCTION NOTICE: ROOF WORK CURRENTLY IN PROGRESS IN BUILDING 9 **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
Land's End 9-201 Beach Front - Premier
Condo -
$200 - $682 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (79)
Top Reasons to Book:• Stunning Beachfront Views!• Low Density and Well-Maintained Beachfront Complex with Beach Access• Single story layout!• Double adjoining balconies.• Very close proximity to many well know restaurants in the area.Pelican Pointe is a unique and well-maintained community with only 14 other units sitting right on the beach
Pelican Pointe 4C
Condo -
$177 - $630 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
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 7-304 Beach Front - Premier
Condo -
$125 - $685 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (44)
This stunning Bay front condo has been completely renovated including new windows, sliding doors and new flooring. Fully equipped new kitchen with custom cabinets, granite counter top and stainless steel appliances. Both bathrooms are remodeled as well with granite counter tops, double sinks in master bath and new walk-in showers in master and gues
Land's End 4-303 Bay Front - Premier
Condo -
$110 - $585 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (14)

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