Vacation rentals with a pool in Pinellas County

4.95 out of 5 average rating, 170 reviews

The backyard showcases a heated pool surrounded by a child safety fence, set against a bright sky. A screened patio is present near the pool, along with a grassy area providing a relaxing outdoor space for guests. The living room features a light grey sofa, a round coffee table, and a wall-mounted TV.

Home in Largo

The Palm House | Heated Pool

Our updated pool home is ideally situated a few minutes from local beaches, restaurants, shopping, and entertainment, making it a perfect home base for your visit. The backyard boasts a heated pool, outdoor shower, screened patio, and gas Blackstone griddle. The bright living room offers a comfortable space to unwind after a long day, whether you’re streaming a movie or playing games. The kitchen is fully equipped with cookware, utensils, and a coffee station. Pool heating: $25/day or $150/week

4.97 out of 5 average rating, 151 reviews

The Ultimate Vacation Pool Home w/Tiki and Cottage

We've set the stage for a first-class vacation experience and a stylish, retro vacation home like no other! Just a 6 minute drive to beaches and 25 mins to Downtown. Phenomenal backyard with HUGE screened-in tiki hut, a huge 32x17' pool + oversized chess board and a pool bar! And last but not least-- a stylish new GUEST COTTAGE with a kitchenette + full bathroom. Perfect for the "guest of honor" or bachelorette accommodations! This home is unique and will exceed your vacation home expectations!

A vibrant mural reading 'Sunshine State of Mind' adorns the exterior wall of the house near the saltwater pool. Smooth concrete surrounds the pool, and large windows provide a view into the inviting indoor space, contributing to a cheerful outdoor atmosphere.

4.95 out of 5 average rating, 117 reviews

Heated Pool & Hot Tub 0.7 mile from Beach

Welcome to our beach house! This is the perfect place for a family vacation or friend getaway. Why We Love The Home: - 0.7 miles from the beach and tons of restaurants/attractions - Resort style backyard with saltwater pool, hot tub, mural for photos and outdoor shower - Quiet and safe neighborhood - Perfect kitchen for entertaining with double ovens Beaches: - 2 min to Indian Shores & Redington Beaches - 10 min to Madeira & Indian Rocks - 20 min to Clearwater & St. Pete Enjoy your stay!

5 out of 5 average rating, 105 reviews

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

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

4.84 out of 5 average rating, 168 reviews

A collage of the beachfront property showcases a private pool surrounded by lounge chairs and vibrant outdoor seating. Coastal views are visible alongside a living area featuring modern furnishings and a flat-screen TV. The picturesque beach is also framed by palm trees, adding to the tranquil setting.

Home in Treasure Island

Eiko Beach House 4BR/3BA Heatd Pool*Hot Tub* Pets

BEACHFRONT HOUSE Private Heated Pool & Spa, Pets OK *** Photos updated Jan 26th 2025 Enjoy amazing sunsets & white sandy beaches from this unique property. About 1/4 acre, beach front property directly on the Gulf of Mexico. Located on a quiet street in Treasure Island, just a few blocks to John's Pass shops. ENJOY great family times, never ending views of sunsets, boating, dolphins, sea birds. Great location walk to John's Pass for great shopping, restaurants, boat rentals, fishing trips.

Bungalow in Indian Shores

A serene outdoor space is revealed through the covered area, featuring a private pool bordered by lush tropical landscaping. Two yellow chairs face the beach, offering views of palm trees and the ocean beyond. Sunlight reflects off the water, enhancing the tranquil atmosphere.

4.95 out of 5 average rating, 153 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

Guest suite in St. Petersburg

A tranquil pool area is surrounded by lush tropical plants and palm trees. Two umbrellas offer shade over lounge chairs, and various potted plants are strategically placed around the perimeter. A paved walkway leads to a covered seating area, enhancing the serene atmosphere.

4.98 out of 5 average rating, 350 reviews

Cozy Casita in NE St. Petersburg

Our Cozy Casita is located adjacent to the main house in a quiet residential neighborhood with a separate entry and fenced in parking space for our Guests. Enjoy our tropical garden and beautiful pool area. The pool is not heated. Small kitchen with Whirlpool electric stove, microwave and mini-fridge. 40” Samsung Smart HDTV and WIFI. Located within minutes of great restaurants, craft breweries, and local museums. Lots of great outdoor activities along St. Pete’s beautiful waterfront.

A spacious outdoor area features a newly designed saltwater pool surrounded by a paved deck. Lounge chairs are positioned near the pool, alongside landscaped gardens with palm and shrub plants. A clear blue sky is visible overhead, complementing the serene setting.

4.99 out of 5 average rating, 105 reviews

Tootsie’s Beachside Retreat

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.

An outdoor bar named Pat's Pub is featured, surrounded by tropical foliage. A pool with a light blue hue is visible in the foreground, complemented by a pink flamingo float. Seating areas include lounge furniture adorned with colorful cushions.

4.88 out of 5 average rating, 168 reviews

*POOL* Bar, Hottub, Central location

Welcome to Pat’s Pub House🌴 Pool, hot tub, & outdoor bar. Peaceful boho vibe. Nature lovers dream! Plants, crystals, & art everywhere. Kids fort with rock wall & sand box. TV you can watch from the pool! Movie projector room with huge comfy couch. Short drive to Florida’s ~BEST~ Beaches, John’s Pass, Downtown St. Pete, & Airports. Central location. 3 bedrooms, 5 beds, 2 baths, dining room, & 2 living rooms. Unique, fun, laidback house. Amazing backyard. Local family owned & operated.

4.93 out of 5 average rating, 100 reviews

An inviting pool area features a clear blue pool alongside a spacious hot tub, both surrounded by a grey stone deck. Comfortable loungers are arranged under an umbrella, offering shade. Sunlight filters through the screened enclosure, creating a bright and open atmosphere.

Home in Largo

Heated Pool and Spa | 5 min to beach

** This house has no checkout requirements - just take your belongings and close the door on your checkout day. ** Experience the ultimate beach vacation in our stunning 3BR home, boasting a brand-new (Jun 2023), upscale pool for leisurely days under the sun and huge in-ground hot tub for relaxing evenings. The fully-equipped kitchen, thoughtfully arranged, provides all modern amenities. Each bedroom, with its plush bedding, is perfect for relaxation after a day’s activities.

4.93 out of 5 average rating, 161 reviews

The outdoor area featuring a heated pool is surrounded by tropical vegetation. The pool is accompanied by a wooden deck, patio chairs, and a set of steps leading into the water. A screened patio is visible in the background, inviting relaxation.

Home in Largo

Heated Pool Tropical Home 6min drive to the Beach

‣ Heated Pool! 💦 ‣ 6 min drive to an amazing beach! 🏝️ (Indian Rocks, free parking) ‣ 3 BR/2 BA for up to 6 guests ‣ 1 king, 1 queen and 2 twin beds + optional rollout bed 🛏️ ‣ Fun decor, perfect for bday or bachelorette parties! 🎉 ‣ Yoga mats! 🧘‍♀️ ‣ Piano! 🎹 ‣ Board Games! 🎲 ‣ Work station 💻 ‣ Modern Amenities 😎 ‣ Walking distance to Largo golf course, gym and tennis! 🏌️‍♀️ ‣ 5-star customer service 🤝 Long-term stays are welcome! Please reach out for a quote.