Holiday rentals in Pinellas County

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Top-rated holiday rentals in Pinellas County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Oldsmar
4.98 out of 5 average rating, 40 reviews

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!

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
4.87 out of 5 average rating, 430 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.

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
4.95 out of 5 average rating, 188 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

Superhost
Home in Seminole
5 out of 5 average rating, 3 reviews

10 Min to Beach: FREE Heated Pool - Hot Tub

🌴 Welcome to Seminole Palms Getaway — your private 2-story Florida retreat with 4 beds / 3 bathrooms tucked into beautiful Seminole, just 10 minutes from the beach. 🌴 Spend your days exploring the Gulf Coast, then come home to float in the heated pool, soak in the hot tub, grill dinner outside, and unwind around the gas fire table under the Florida sky. Pool heating is complimentary from October 15 through April 15 and heated to 85°F. Temperature may vary based on weather and time of day.

Top guest favourite
The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.
Villa in Largo
4.98 out of 5 average rating, 168 reviews

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.

Top guest favourite
The exterior of the guest house showcases a charming single-story structure with a light-colored façade. Lush greenery, including palm and decorative plants, borders the neatly manicured lawn. A spacious driveway leads to a two-car garage, framed by tall trees under a clear blue sky.
Home in Pinellas Park
4.98 out of 5 average rating, 119 reviews

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.

Guest favourite
A light-filled living area is furnished with a comfortable grey sofa and two wooden chairs. A round coffee table sits in the center on a natural fiber rug. A wall-mounted TV displays a scenic view, while large windows with blinds allow natural light to enter.
Home in Largo
4.93 out of 5 average rating, 151 reviews

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.

Top guest favourite
Home in Palm Harbor
5 out of 5 average rating, 37 reviews

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Welcome to Seaside Sanctuary 🌊🌅 – Your Ultimate Waterfront Escape Nestled in charming Crystal Beach, this spacious 4-bedroom, 2.5-bath retreat perfectly blends luxury, comfort, and coastal fun. Go kayaking from your direct Intracoastal access, soak in unobstructed sunsets, relax in the hot tub, challenge friends in the game room, or grill a delicious meal on the patio 🥙. Perfect for family reunions, bestie getaways, wedding weekends—or simply because you deserve a seaside escape!

Top guest favourite
Home in Largo
5 out of 5 average rating, 14 reviews

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🏝️.

Top guest favourite
Guest house in Seminole
4.95 out of 5 average rating, 41 reviews

Cozy Private Studio+Hot Tub+Workspace | Near Beach

🏡 Private Cozy Studio Stay in a completely private studio with its own private entrance and dedicated 🧑‍💻workspace, just minutes from the beaches and natural parks. 🛁 Private Outdoor Jacuzzi Unwind and relax after a day at the beach or exploring the area. 🍳 Fully Equipped Kitchen Prepare meals easily during your stay. 📍 Great Location Close to restaurants, shops, 🏖️beautiful beaches, and natural parks perfect for couples or travelers seeking a peaceful coastal getaway.

Guest favourite
Home in Seminole
5 out of 5 average rating, 10 reviews

The Captain’s Rest

Relax in this updated Seminole retreat just 5 minutes to Madeira Beach and 3–5 miles to Gulf beaches. Enjoy 2 bedrooms, 2 baths (including a Captain’s Bath in the garage area), a full kitchen, office with dual desks, and plantation blinds throughout. Outdoor amenities include a hammock, sectional sofa, TV, firepit, cornhole boards, and a grill. Board games galore for rainy days. Dunkin’ Donuts is at the end of the street!

Top guest favourite
The image showcases four distinct areas of Coastal Palms. A cozy sleeping area is highlighted with a spacious bed and natural light. The outdoor space features a ping-pong table, seating under a large umbrella, and a welcoming hot tub, surrounded by colorful striped walls.
Home in Largo
5 out of 5 average rating, 50 reviews

Hot Tub | Ping Pong | Foosball | Mins to Beaches

Welcome to Coastal Palms, your private Gulf Coast retreat just minutes from Indian Rocks Beach. This beautifully updated mid-century home blends coastal charm with modern comfort, featuring a private hot tub, game lounge, backyard oasis, and space to relax after a day at the beach. Whether you're planning beach days, family vacations, or weekend getaways with friends, Coastal Palms was designed for making memories. 🏓

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