Holiday rentals in Highpoint

Serenity Palms of Pinellas

Newly Renovated and peaceful/private 3 bedroom 1 bath (home with a large private back yard and porch. This beautiful home is centrally located to absolutely everything! 20 mins to Tampa Airport, 20mins to beautiful white sandy beaches, 20 minutes to downtown St. Petersburg, local horseback riding trails, biking trails, kayaking, etc. Come and enjoy this beautiful home after a fun filled day exploring the town. This home comes with high speed wifi, cable, washer and dryer, private parking & more.

Large Coastal Cottage Close to Top Beaches

Welcome to our stunning 2-bedroom, 1-bath unit, designed for comfort and relaxation. Enjoy a renovated full-size kitchen and spacious bedrooms, including a master bedroom with a queen bed and a second bedroom featuring a full-size bed with a twin pull-out trundle bed. The living room offers additional sleeping with a queen-size memory foam sofa sleeper. Step outside to your own backyard paradise, complete with outdoor lighting, stylish furniture, a fire pit, BBQ grill, and fun outdoor games.

Clearwater | Pet Friendly | 8 PPL | Great Location

Welcome to your perfect getaway! This 3-bedroom, 2-bath home offers comfort, convenience, and plenty of fun for your stay. Enjoy a spacious layout with a large backyard—perfect for relaxing or entertaining. The home is centrally located, just 15 minutes from Tampa International Airport and Downtown St. Petersburg, with easy access to major highways, shops, and restaurants. Whether you’re here for business or leisure, this property provides the ideal blend of relaxation and accessibility.

Home in Downtown Dunedin, 2b/1b+yard, near beaches

A stunning, updated 2-bedroom bungalow located in Delightful Dunedin! This is the perfect place to stay while enjoying our top-rated gulf beaches, bustling Main Street, Major League games, Pinellas Trail, and greater Tampa Bay. Centrally located, only 6 miles to Clearwater Beach, Honeymoon Island and Caladesi Island State Parks, one block from the Pinellas Trail, and only STEPS (400ft) to Main Street! *See house rules for bringing one dog, no exceptions, $30 per day for the pup.

Watch the Sunrise at Sunrise! @ Clearwater home.

Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

St Pete airport /ClearWater Ice Arena/beach/Unit B

This apartment is part of a duplex side by side, this unit is one level with no stairs, both units are used for Airbnb. It’s equipped with everything you need for your vacation, just 7 minutes from the Clear Water airport, 20 min from Tampa International airport, 25 min to the beach, 35 minutes St Pete, 35 minutes Tarpon Spring. The house is not completely fenced in, and it has big yard that is shared with the other unit. Just 4 minutes to Clearwater Ice Arena.

Pool, Playset, 15 min to Pier 60 @ Cove Cay Oasis

Welcome to Cove Cay Oasis, your perfect getaway in Clearwater! This beautifully remodeled 3-bedroom, 2-bath home is designed for comfort and fun. Relax in the private pool, enjoy evenings by the fire pit, or let the kids play on the swing set. Nestled in a prime location, you're just minutes from stunning beaches, lively downtowns, and top attractions. Whether you're here to unwind or explore, Cove Cay Oasis is your home away from home. Book your stay today!

Vacation destination 4 bedroom house

No mandatory evacuation zone. This stylish place to stay is perfect for group trips, very spacious 4 rooms and common areas, every room has a ceiling fan and Smart TV . Location is perfect, 5 min to US 19, 20 min to Tampa Airport, 20 min to downtown, 20 min to beaches, safe and quiet neighbourhood. Backyard is completely fenced and private, gigantic deck on 3 sides of the house with 3 entrances , fire pit, and gas grill. Pets are welcome here!!

10 Minutes to Beaches! Thyme (to Coast) House

Ready to create lasting memories? Book your Florida dream vacation today! Unwind and recharge at this perfect Florida getaway! Our charming rental is just minutes from the stunning beaches Pinellas County offers. Soak up the sun and crystal-clear waters, all within a 10-minute drive. Need to stay connected? We've got you covered with blazing-fast 1G Wi-Fi and a dedicated workstation, making it easy to balance work and play during your stay.

Boutique Bungalow with Private Saltwater Pool

Relax in a crisp Florida bungalow with a private saltwater pool set in a fully private backyard oasis. Whether you are coming to Tampa for an event, extending your cruise vibe, or coming to Tampa for work, this home has got you covered. You’ll be 15 minutes from the Tampa Convention Center and the Port Tampa Bay Cruise Terminal, close to South Tampa dining and nightlife, 10 minutes to TPA, and an easy drive to award-winning Gulf beaches.

Villa Italia "Villas by Christine"

Perfect location, Charming Villa!! Guests are loving the newly renovated Villa Italia. Two luxury Masters with separate bathrooms - one upstairs & one down. Within the upstairs bedroom you have a queen size bed along with a full size couch for lounging during the day. We are pet friendly. Please let us know you will be bringing your pet. Pet fee of $100. can be paid beforehand or is due upon arrival.

#13 Near Clearwater airport home

Experience the fun of Florida with ease in this 2-bedroom, 1 bath vacation rental. Offering a full kitchen, Smart TV, this home is perfect for sharing memory-filled moments! Located in Clearwater FL, this property just across the bridge to Tampa and allows for beachside days at spots like Indian Rocks Beach Nature Preserve or Clearwater Beach.