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
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.
Condo 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
A clear blue pool is surrounded by lush greenery, including palms and other tropical plants. A red umbrella provides shade over a seating area nearby, while lounge chairs are positioned along the pool's edge, inviting relaxation in a serene outdoor setting.
Guest suite in Largo
4.97 out of 5 average rating, 403 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Top Guest favourite
An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.
Home in Seminole
4.99 out of 5 average rating, 155 reviews

Tootsie’s Beachside Retreat-New Heated Pool

LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

Top Guest favourite
A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 204 reviews

Luxury Beach Cottage | Walk to Dining & Sunset

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

Top Guest favourite
A spacious balcony is bordered by tall palm trees, offering a view of the calm Gulf of Mexico and white sand beach. The clear blue sky complements the serene ocean, creating a tranquil setting for relaxation.
Condo in Indian Rocks Beach
4.89 out of 5 average rating, 103 reviews

Gulf-View 2BR/2BA Beach Condo!

This Indian Rocks Beach Gulf Front Hamilton House building is located directly on unique Clearwater- St.Pete white sand beach with private beach access and heated pool, washer and drier in the unit. Our 3rd floor 1100 sq. feet 2 bedroom condo #207 offers a spacious balcony bordered with palm trees with northerly nice side view of the Gulf of Mexico and white sand beach that goes on for miles. Two assigned parking spaces (one under the building and second uncovered).

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
Home in Seminole
4.99 out of 5 average rating, 204 reviews

Resort Pool Home with Pool Cabana 🏝6 MIN to BEACH-

Discover this glamorous 3-bedroom, 2-bathroom home that sleeps 12 guests. Beautiful saltwater pool, resort-like cabana complete with a TV and beverage fridge, tiki counter/bar seating and outdoor dining area. The guest bungalow with its vanity glam station is a real highlight, too! Just 6 minutes from stunning beaches and 4 minutes to Seminole Town Center, this location is unbeatable. Each room boasts a smart TV and is immaculately decorated and professionally cleaned.

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.
Condo 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
Home in Clearwater
4.91 out of 5 average rating, 119 reviews

Pet-friendly Beach Home with Heated Pool & Spa

Relax in style at our modern beach home, boasting a spacious layout and easy access to local attractions. Dive into pure Beach Bliss with a heated saltwater pool (Nov 1 - May 1) and a soothing hot tub—your perfect getaway awaits! Nestled in a peaceful, safe and friendly neighborhood near Eagle Park, just minutes from Clearwater and Indian Rocks Beaches, enjoy scenic bike trails and local attractions. Bring your furry friends along for a pet-friendly adventure!

Top Guest favourite
Apartment 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.
Condo 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

Guest favourite
A comfortable living area is presented with a spacious sectional sofa adorned with decorative pillows. A large flat-screen TV is mounted on a wooden accent wall, enhancing the cozy atmosphere. The open layout leads towards a bright kitchen visible in the background.
Condo in Indian Rocks Beach
4.93 out of 5 average rating, 123 reviews

Golf Cart, 2 bed 2 Bath, Heated Pool

The Chunky Mermaid is new with tasteful decorations to pull the space together. Big 75" TV, big double queen guest room, and king sized master bedroom. The Chunky Mermaid is the perfect beach house to get your toes in the water in minutes, the perfect beach community to walk to local cuisine, with the perfect creature comforts of home. The space is built for families/groups that want to have fun together with epic sunsets perfect for sun downers.

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