Holiday rentals in Pinellas County

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Top-rated holiday rentals in Pinellas County

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Guest favourite

Guest house in St. Petersburg

4.97 out of 5 average rating, 230 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!!!

Guest favourite

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, 422 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.

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

4.97 out of 5 average rating, 180 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

Guest favourite

A light-filled living area features a comfortable white sofa and a wooden coffee table with decorative items. A flat-screen television is positioned on a stylish console. Dining space is provided with a wooden table and chairs. Blue walls and ceiling fan contribute to the airy atmosphere.

Home in Seminole

4.95 out of 5 average rating, 20 reviews

Cozy 2BR Villa in Seminole FL with Pool

Welcome to your sunny home base in beautiful Seminole, Florida! Whether you're here for a beach getaway, to explore nearby parks, or just to relax and unwind, this charming 2-bedroom, 1-bathroom villa offers the perfect balance of comfort, convenience, and coastal style. The property also has a community pool tennis court and basketball court available. Located just a short drive from some of the Gulf Coast’s most beautiful beaches—including Madeira Beach, Redington Beach, and Indian Rocks.

Top guest favourite

The three-story guesthouse features a blend of wood siding and large windows, surrounded by lush greenery. A spacious balcony is present on the second level, offering a shaded outdoor space. Tropical plants and trees frame the entrance, enhancing the serene ambiance of the property.

Cottage in Seminole

5 out of 5 average rating, 101 reviews

Florida Guest House

Seminole Oaks House...Beautifully appointed new construction 2-story Guesthouse located in a very quiet setting 10 minutes from Indian Rocks Beach. Walking/biking distance from Walsingham Park and Lake and the Pinellas Trail. Enjoy your morning coffee or evening glass of wine on the balcony..or tree shaded rear Patio w/BBQ grill..Great location for exploring all Pinellas has to offer including the Beaches, Downtown St. Pete,and open air Markets..dedicated parking..very peaceful and private ..

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, 165 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

Guest suite in Largo

5 out of 5 average rating, 112 reviews

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks

Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

Top guest favourite

An outdoor space is illuminated by sunlight, featuring a heated pool surrounded by comfortable lounge chairs. A new hot tub occupies a corner, while a cozy seating area provides a space for relaxation. A screened enclosure maintains a pleasant atmosphere.

Home in Largo

4.98 out of 5 average rating, 298 reviews

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

If you like pops of color, modern decor a FREE HEATED pool seasonally Oct 15-April 15 (80-85 degrees) HOT TUB , RARE SAUNA, TIKI BAR fire pit and everything new then this house is for you! BRAND NEW HOT TUB installed 4/2025!!! Very Close to shopping and beaches perfect dedicated vacation home! We are family owned and operated and dedicated to you and your vacation experience. Message me if you have any questions! SUPER FAST WIFI 753Mbps - (1 G if you plug into modem) verified by Airbnb

Top guest favourite

Home in Oldsmar

4.97 out of 5 average rating, 38 reviews

Modern Private Estate | Central to Tampa & Beaches

Experience a 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, and guests who value quiet and thoughtful design!

Top guest favourite

A single-story house is shown with a neatly landscaped front yard. A concrete driveway leads up to an attached garage. The exterior features soft green tones complemented by white accents, with shrubs and plants adding greenery along the sides.

Home in Pinellas Park

4.92 out of 5 average rating, 74 reviews

Hammock Haven

Keep it simple at this peaceful, centrally-located home; featuring a complete makeover inside and relaxing, tropical outdoor space. Enjoy new rainfall showers, new appliances, dimmable lighting, high speed wifi with smart TV in each room, work space with wireless printer, outdoor dining space, BBQ grill, and shaded hammocks with a private tropical feel. Centrally located to all of Tampa Bay's most beautiful beaches, downtown Saint Petersburg, and downtown Tampa.

Superhost

Home in Seminole

4.9 out of 5 average rating, 305 reviews

Beachy Home Minutes from sugary sand beaches

Sunny Florida Beach Home! 4 minutes drive to the #1 best beach in America nominated by Trip Advisor, where you will find beautiful white sand and extremely warm and clear water! Enjoy tons of top local restaurants and entertainment all minutes from your door in this relaxing, low key beach neighborhood. Super kid friendly! Games, BBQ, swing set, Apple TV, and bikes for the whole family! Enjoy the entire house that has been completely remodeled and is sparkling CLEAN!

Guest favourite

A bright living area features a comfortable sectional sofa with decorative pillows, paired with a tropical-patterned armchair and ottoman. Natural light streams through the windows adorned with sheer shades, highlighting a wooden coffee table and a cozy area rug on the floor.

Home in Largo

4.92 out of 5 average rating, 417 reviews

Live Oak Lodge

Enjoy your stay in this 1950s tropical home in a quiet neighborhood only 3 miles from the beach. Two premium beach chairs, rolling cooler, umbrella and more to use during your stay! Hang out surrounded by the tropical plant life in the backyard. Cozy string lights drape the 6 foot privacy fence in the backyard. This is part of a duplex unit (another unit is attached to this one), but everything is private inside and outside. (No pets allowed :-))