Resort Rentals - Florida Vacation Rentals Beach Vacation

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 279 properties available
***CONSTRUCTION NOTICE, PLEASE NOTE: Building #1 will be under renovation 5/1/23 - 8/26/23. The online rates over those dates reflect a discount for the inconvenience and noise that will be present during this time.***Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal
Land's End 1-307 Gulf View
Condo -
$99 - $418 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (73)
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 offer
Land's End 11-302 Beach Front - Premier
Condo -
$182 - $492 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (4)
***CONSTRUCTION NOTICE, PLEASE NOTE: Building #1 will be under renovation 5/1/23 - 8/26/23. The online rates over those dates reflect a discount for the inconvenience and noise that will be present during this time.***Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal
Land's End 1-208 Bay Front - Premier
Condo -
$108 - $452 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (62)
Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit PLUS the kitchen appliances have been recently replaced with gorgeous stainless steel appliances. • 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
Trillium 1C - Premier
Condo -
$182 - $488 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (91)
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 7-305 Beach Front
Condo -
$165 - $458 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (87)
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
$220 - $603 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (42)
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. The big wrap-around balcony and the extra windows and doors give this
Villa Madeira 301 - Premier
Condo -
$182 - $506 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (157)
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! Vacation memories await yo
Madeira Del Mar 205
Condo - Pet Friendly
$220 - $603 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (19)
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 units 1 and 2 - Downstairs
Condo
$220 - $621 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Top Reasons to Book:• Stunning Views of the Gulf of Mexico from the moment you enter the condo. • Enjoy the fabulous complex amenities such as the shared outdoor pool, lounge chairs and beach access. • make long lasting memories while you grill out and dine at the shared BBQ/picnic area. • Tasteful, stylish upscale furnishings inside and out.Welcom
Madeira Vista 201
Condo -
$163 - $457 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Top reasons to book: • Best of both worlds! Gorgeous sunrises from your private balcony, famous sunsets in your back yard• Beautifully decorated throughout to reflect coastal comfort.• 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
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 2 407
Condo -
$160 - $385 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (14)
Top Reasons to Book: •Admire incredible sunsets on the private, screened-in balcony, which is also great for outdoor dining! •Arie Dam offers wonderful amenities such as a heated pool and spa as well as a beachside BBQ grilling area. •The location is great too! Close to popular John's Pass which offers a variety of restaurants, entertainment, and
Arie Dam 304
Condo -
$204 - $515 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (168)

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