Holiday rentals with a pool in Pinellas County

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Top-rated rentals with a pool in Pinellas County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
Apartment in Clearwater
4.98 out of 5 average rating, 102 reviews

Lovely Condo minutes from beach & King bed

Kick back and relax in this calm, stylish space.Minutes away from Clearwater Famous Beach.You will be pleased with high ceilings and open floor plan.King size bed in the Bedroom with balcony and 55" smart Tv. Walk-in closet and updated bathroom. Spacious covered patio style balcony. Full-size washer and dryer inside the unit. Fully updated and equipped kitchen. Specious living room with a sleeper sofa that can sleep two quests and 65"smart Tv. Heated outdoor pool, gym, fast wifi internet, cable

Guest favourite
The outdoor area showcases a saltwater pool within a screened lanai, surrounded by a patio area with seating. The pool area is illuminated by natural light, enhancing the space's openness. A game room features plush seating arranged for viewing films, with walls designed for a cinematic experience.
Home in Clearwater
4.93 out of 5 average rating, 174 reviews

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

Superhost
A private inground pool is surrounded by a paved patio with lounge chairs and umbrellas for shade. The tranquil water reflects the sky, while tropical plants encircle the area, adding greenery to the serene outdoor space.
Home in Largo
4.89 out of 5 average rating, 134 reviews

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

Guest favourite
A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.
Guest house in St. Petersburg
4.91 out of 5 average rating, 154 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Keep it simple at this peaceful and centrally-located place. La Casita is located minutes from bustling downtown and beautiful bay waterfront restaurants and bars. Tampa International Airport is only 20 minutes away. The property itself is great for relaxing. La Casita is surrounded by lush palm trees and has its own access to the pool a few feet from your front door. Come relax, go to the pool, beach, enjoy the outdoor shower and finish off the day at One of the many nearby restaurants!

Top guest favourite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Apartment in Treasure Island
4.99 out of 5 average rating, 211 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Top guest favourite
An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 174 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Top guest favourite
A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.
Apartment in St. Petersburg
4.98 out of 5 average rating, 283 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

Guest favourite
Villa in Largo
4.9 out of 5 average rating, 124 reviews

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. ​FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. ​PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. ​ Essentials: ​🌞 Heated Swimming Pool (Private!) ​🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! ​🛏️ 4 Queen/Full Beds ​🧺 Beach Amenities

Guest favourite
A serene waterfront view is offered from the balcony, featuring a round table with two chairs. Palm trees frame the view, while calm waters reflect the clear sky, creating a peaceful outdoor space perfect for relaxation.
Apartment in St. Petersburg
4.81 out of 5 average rating, 215 reviews

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

Top guest favourite
An open living area features a modern kitchen with white cabinetry and a large island with bar seating. A comfortable couch is positioned in front of an electric fireplace, accompanied by a coffee table displaying books and a decorative plant. A wall-mounted TV displays a vibrant underwater scene.
Apartment in Seminole
4.98 out of 5 average rating, 251 reviews

SHEEK and Glam- heated pool Updated! 3 mi to beach

UPDATED modern Light and bright colorful condo w FREE HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/restaurants and the Pinellas trail !

Top guest favourite
Flat in St. Petersburg
4.94 out of 5 average rating, 127 reviews

Waterfront studio! Heated pool and hottub

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

Top guest favourite
A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.
Apartment in Clearwater
4.99 out of 5 average rating, 148 reviews

Ocean Breeze • Easy - Heated Pool Access

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

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