Holiday houses in Pinellas County

4.96 out of 5 average rating, 54 reviews

Private Pool Oasis | 4BR • Game Room • Mini Golf

Great for families and located in a quiet neighborhood, this spacious home is designed for relaxing and fun-filled stays. Enjoy a private pool, mini golf, and indoor games like a pool table, darts perfect for everyone with 4 bedrooms and comfortable living spaces, it’s ideal for quality time together, just minutes from beaches, dining, and shopping. Whether you're visiting for the beaches, nature, family activities our location puts you close to everything Largo and the Gulf coast have to offer.

LocationFamilyBathroom

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 250 reviews

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

FamilyValueIndoor spaces

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 302 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

FamilyLocationHot tub

Superhost

A unique dome structure is surrounded by a landscaped area featuring low plants and trees. The exterior is composed of light-colored bricks, while two arched windows provide natural light. A tall tree with hanging moss is visible alongside the dome, contributing to the serene setting.

Dome in Largo

4.86 out of 5 average rating, 453 reviews

Blue Moon Dome > Cozy Romantic Beach Retreat

• Full private dome house. • Walk to Florida Botanical Gardens & Pinellas Trail • 7 min to white-sand beaches, restaurants, cafes, shopping • Romantic queen bed under a skylit dome • Airy, cozy, filled with light - a perfect escape from the ordinary • Fast Wi-Fi, kitchen, private entry, free parking • Optional romantic room setups with candles, petals & treats Whether it’s a honeymoon, birthday surprise, solo reset, or anniversary adventure - Blue Moon Dome is more than a stay. It’s a memory.

LocationFamilyHeating

4.91 out of 5 average rating, 196 reviews

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

ValueFamilyBeach

4.95 out of 5 average rating, 199 reviews

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

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

ValueFamilyKitchen

4.88 out of 5 average rating, 40 reviews

The Palm Villa-Pool, Sauna, Hot tub, theater, golf

Welcome to The Palm Villa—a thoughtfully curated luxury retreat designed for guests who value calm, privacy, and refined comfort. Inspired by tropical elegance, this serene villa blends lush surroundings with modern sophistication, creating the perfect escape for relaxation and indulgence. ☆ 5 miles to beach ☆ ☆ pool , Sauna , Hot tub, Fire pit , BBQ grill ☆ Movie , karaoke, Pool Table, Foosball, Basketball, Golf , Bowling, Yoga ☆ Fully stocked kitchen and Coffee ☆ Home office work station

LocationFamilyCondition

5 out of 5 average rating, 20 reviews

Home in Seminole

NEW 3BR Sunny Retreat | Pet-Friendly+Mins to Beach

Welcome to your Seminole escape in sunny Florida - a cozy, family-friendly 3BR/1BA home just a short drive from the beautiful shores of Madeira Beach and Indian Shores. Thoughtfully designed for comfort and ease, this inviting retreat is the perfect home base for beach days, family time, and exploring Florida’s stunning Gulf Coast. 🌟 Madeira Beach – 5 min drive 🌟 Tampa International Airport – 30 min drive 🌟 Downtown St Pete – 25 min drive 🌟 John’s Pass Village & Boardwalk – 12 min drive

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5 out of 5 average rating, 18 reviews

Home in Clearwater

Designer Home | 10 Min to Dunedin Waterfront

Designer home 10 min to Downtown Dunedin, 15 to Honeymoon Island and Clearwater Beach. Sleeps 6: king bed, queen bed, and queen sleeper in a flex/office room. Two renovated baths with rain shower, open kitchen with large granite island, Nespresso coffee bar, and dining for 6. Private fenced backyard with covered patio lounge, outdoor dining with grill, and a second lounge under the palms. Game room with ping pong. Your home base for beaches, spring training, and the best of the Gulf Coast.

LocationFamilyHospitality

A stylish kitchen countertop is displayed with woven baskets containing a water bottle and miscellaneous items. A sign, featuring the phrase 'THIS IS OUR HAPPY PLACE,' is positioned prominently, adding a touch of character to the modern, open space.

4.98 out of 5 average rating, 49 reviews

Lakeside Heaven Retreat in Largo - King size Bed!

Welcome to Largo, and to our fully renovated home! This spacious and centrally located retreat offers plenty of room for fun and relaxation. Just a 10-minute drive to Belleair Beach and less than 15 minutes from the award-winning Clearwater Beach. With Highland Largo Park right next door, you can step outside and immerse yourself in a peaceful natural setting, complete with scenic walking trails and a beautiful lake just steps from your front porch. We look forward to hosting you!

ValueFamilyKitchen

Apartment in St. Petersburg

4.97 out of 5 average rating, 166 reviews

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

ValueFamilyBackyard

A bright living room features a large gray sofa adorned with colorful cushions. A light wood coffee table sits at the center, while a flat-screen TV is mounted on a white unit. Natural light illuminates the space through sliding glass doors, leading to a backyard.