Holiday rentals in Pinellas County

Modern Private Estate | Central to Tampa & Beaches

Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!

Relax in private Heated pool Family-Friendly comfo

🌴 Outdoor Paradise Your private backyard is the star of the show. A 10,000-gallon PebbleTec heated pool (up to 8 ft deep) anchors a resort-style outdoor space designed for pure Florida living — complete with a cantina bar for poolside drinks, teak lounge seating, chaise chairs, resort umbrellas, and lush landscaping that gives you the perfect balance of sun and shade. Fire up the Weber propane grill and let the evening take care of itself. 🍳 Fully Equipped Kitchen Cook like you mean it or kee

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.

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

The Guest House

The Guest House is a coastal themed 2100 sq ft house, split floor plan, 3 bedrooms & 2-1/2 baths for sleeping 6 comfortably. The Guest House is nestled in a quiet neighborhood in Pinellas Park, FL & is a favorite family vacation get-a-way close to beaches & attractions. Enjoy the Master Suite with an adjustable Sleep Number king bed & Master Bath with garden tub, shower & walk-in closet. After a day of enjoying the beaches or attractions, relax, & unwind on the private screened lanai.

12 Mins to Beach | Patio&Grill | Fenced Yard

Relax in Style at This Centrally Located 2-Bedroom Home. Nestled in a quiet residential neighborhood in Largo, this charming home is just minutes from local shops and restaurants. Whether you're here for a beach getaway, a business or family trip, it's the ideal spot to call home during your visit. After a day spent soaking up the sun at the beach or exploring the nearby parks and charming towns, return to your cozy retreat, perfect for unwinding and recharging for your next adventure.

Boutique Stay Near the Bay | Walk to Downtown.

Feel both transported and perfectly at home. The Barefoot House is your serene escape in the heart of Historic Old Northeast — where charm, comfort, and culture meet. Tucked away in a quiet alley, this thoughtfully designed retreat is just blocks from St. Pete’s stunning waterfront parks and a 5-minute stroll to downtown’s vibrant mix of restaurants, cafés, bars, museums, and art galleries. Guests love our blend of calming details & walkable access to everything St. Pete has to offer.

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

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!

Modern 3BR w/ Basketball Court, Pool & Hot Tub

Welcome to the perfect family-friendly getaway! This modern home is cozy, immaculate, and stunningly decorated (approx 1000sq ft). Enjoy endless entertainment with a private basketball court, outdoor TV, sparkling pool, and soothing hot tub. Inside, the game room boasts a pool table, dartboard, and TV, while every bedroom is equipped with its own TV for your convenience. Just minutes from the beautiful Gulf beaches, this home has everything you need for an unforgettable stay!

Oceanfront Condo | Rooftop Terrace | Arcades |

Picture this: you step onto the rooftop as the Gulf stretches out in front of you — golden hour, warm breeze, a putting green underfoot and nowhere else you'd rather be. Back inside, the kids are deep into NBA Jam while the waves crash just beyond the balcony. Hello Sunshine is a direct oceanfront condo in the heart of Indian Shores, designed like a magazine spread and stocked for the kind of trip people talk about long after they've unpacked.

2BR | Oceanfront, Backyard Beach, Fully Equipped

Experience luxury coastal living at Indian Shores in this beautifully appointed beachfront retreat at Sunplace. Featuring 2 spacious bedrooms with a king and queen bed, plus a full-size roll-out bed and Pack ’n Play, this fully equipped condo is perfect for families and groups. Enjoy direct beach access, stunning Gulf surroundings, resort-style amenities, and easy access to local dining, shops, and nearby Clearwater Beach.