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 311 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 9-304 Beach Front - Premier
Condo -
$141 - $492 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (77)
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 6-205 Beach Front - Premier
Condo -
$141 - $492 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (80)
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 -
$136 - $385 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
The Harbor At Town Center is a brand new property in Madeira Beach!Top reasons to Book:• Private and beautifully furnished balcony overlooking the marina!• Just a block from beautiful, white sand Madeira Beach!• Wonderful amenities such as a pool and spa as well as free Wi-Fi, secured parking, and an in-unit washer and dryer!• Beautifully decorated
The Harbor Condo 305 - Premier
Condo -
$170 - $587 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
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 4-202 Bay Front - Premier
Condo -
$122 - $452 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (22)
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 8-204 Beach Front - Premier
Condo -
$141 - $492 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (75)
Top reasons to Book: • Newly renovated Kitchen with brand new appliances! • All the Amenities- Beachfront heated pool, hot tub, shared BBQ Area, Free wifi & 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! New Pictures Coming S
Sea Breeze 401
Condo -
$400 - $485 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (69)
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 is
Tides 6-563
Condo
$145 - $345 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 -
$141 - $492 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (39)
New Photos Coming Soon!!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 inform
Upham Beach Inn - #12 1BR Suite
Apartment
$115 - $286 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Top Reasons to Book: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs & access to the heated saltwater swimming pool during your visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. Many updates have been made in this Gulf front condo. The renovated k
Villa Madeira 505 - Premier
Condo -
$151 - $491 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (119)
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 Beachfron
Sunset Vistas 302S
Condo -
$135 - $524 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (8)

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