Holiday rentals in Belleair

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Top-rated holiday rentals in Belleair

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Guest favourite
Home in Clearwater Beach
4.95 out of 5 average rating, 112 reviews

Waterfront Coastal Bliss at Brightwater w/ Heated

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Guest favourite
Apartment in Sand Key
4.94 out of 5 average rating, 17 reviews

CBC 1-15E–High-End Stay, Low Seasonal Pricing!

🌴Luxury Beachfront Condo at Crescent Beach Club 15E | Spectacular Gulf Views & Resort Amenities Looking for the perfect coastal escape? Look no further than Crescent Beach Club 15E in Clearwater Beach, managed by Sandy Feet Vacation Rentals! This luxurious 2-bedroom, 2-bath condo on the 15th floor offers breathtaking Gulf of Mexico views from every room. Fully updated with modern coastal décor, this beachfront retreat provides waterfront living at its finest, featuring three private balconies!✨

Top guest favourite
A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.
Cottage in Belleair
4.99 out of 5 average rating, 77 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Welcome to our newly renovated vacation home in beautiful Largo, Fl. This adorable bungalow is located just mins from the area’s most pristine beaches- Indian Rocks Beach, Clearwater Beach, etc! An added bonus is that the home is right on the Pinellas Trail & bikes are even provided for your pleasure! There is a huge game room with TV, arcade and fooz ball. Plunge pool & fire pit! This home is the perfect vacation spot for families looking to enjoy all this charming coastal town has to offer.

Top guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.98 out of 5 average rating, 164 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favourite
The living area is furnished with a light-colored sofa and an ottoman, offering comfortable seating. A smart TV is mounted on the wall, and a wooden dining table is visible nearby. A ceiling fan provides airflow, with natural light filtering through a nearby window.
Guest house in Clearwater
4.94 out of 5 average rating, 100 reviews

Adorable Vintange Style guest house-King size bed

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style Guest house. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable guest home features unique layout with Vintage-modern decor, free WiFi, smart TV, LVT flooring and sleeps up to 4 people. It also offers one free parking.

Top guest favourite
A serene outdoor area features a sparkling pool and a raised jacuzzi, both surrounded by a patio with colorful planters. An umbrella casts shade over a seating area, while vibrant yellow and blue accents add a lively touch to the space.
Home in Safety Harbor
5 out of 5 average rating, 12 reviews

Luxe Pool Residence | Downtown | Central Located

A beautiful, spacious three bedroom - all ensuite and 4 baths home in downtown Safety Harbor featuring a private backyard pool and jacuzzi. Perfect for family vacations with lots of areas to lounge and only one block from Main Street. Includes large bedrooms, living spaces, and a huge open Chef's kitchen as well as outdoor kitchen/grill. There is a separate office and two washers/dryers. High quality furniture and bedding. You will not be disappointed. We look forward to hosting you!

Top guest favourite
A welcoming porch area is seen, featuring two white rocking chairs and a small side table. Lush greenery and blooming flowers surround the space, while a door leads inside. Light reflects off the stone flooring, complementing the vibrant green walls.
Home in Largo
4.98 out of 5 average rating, 108 reviews

Walk to beach shops food drinks “The Inbetween”

This is one of Island Rum Suites collection! Stay with us to see why we are one of the best family owned and operated around! We are in a quiet and safe neighborhood, walking distance to the beach, shopping, restaurants, nature parks, water park, pizza, pubs and ice cream! All guests must be listed on the reservation in order to be on the property and accounted for, even children. Zoning allows 2 people per bed and 2 cars No pets allowed Florida State License # DWE6215889

Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a screened enclosure. Lounge chairs are positioned poolside, and a children's swing set is visible in the background. The vibrant sunset creates a warm ambiance over the tranquil setting.
Home in Seminole
4.95 out of 5 average rating, 133 reviews

Sleeps 8 Near Beach | Pool + Game Retreat

Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

Guest favourite
Townhouse in Tampa
5 out of 5 average rating, 6 reviews

Tampa 3BR Townhome I Family-Friendly | Garage

Welcome to a Coastal-themed 3 Bed / 2.5 Bath townhome with a 2-car covered garage. Enjoy bright décor, 2 inviting living areas, a fully equipped kitchen, perfectly curated for style, comfort, and convenience. Upstairs offers three serene bedrooms with plush bedding. Perfect for families, couples, or long stays—just 20 mins to the Tampa airport and close to Tampa’s top shopping, dining, and beautiful world class Gulf Coast beaches.

Guest favourite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Apartment in Indian Rocks Beach
4.97 out of 5 average rating, 154 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Top guest favourite
A small outdoor seating area is depicted, featuring two bright green chairs and a matching table adorned with a potted plant. Lush green foliage rises around the space, creating a tropical ambiance. The background showcases a wooden fence and natural elements.
Guest suite in Largo
5 out of 5 average rating, 224 reviews

Cozy Private Bedroom Suite Private Entry King Bed

Spacious private master bedroom suite with private entrance and driveway! King bed. Private spacious bathroom! Fridge, microwave, Keurig coffee maker. Located in a large home. No access to the rest of house. 5 miles to Indian Rocks Beach. 8 miles to Clearwater. 2.5 miles to Botanical Gardens and Heritage Village, both FREE! 30 minutes from Tampa airport and 20 minutes from Clearwater St Pete airport.

Top guest favourite
The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.
Cottage in Oldsmar
4.96 out of 5 average rating, 309 reviews

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Popular amenities for Belleair holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Belleair