Holiday rentals with a pool in Pinellas County

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.

4.88 out of 5 average rating, 150 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

4.99 out of 5 average rating, 112 reviews

Best Celebration - Heated Pool - Hot Tub - Arcade

🌴𝐇𝐨𝐮𝐬𝐞 𝐨𝐟 𝐏𝐚𝐥𝐦𝐬 – 𝐘𝐨𝐮𝐫 𝐏𝐫𝐢𝐯𝐚𝐭𝐞 𝐅𝐥𝐨𝐫𝐢𝐝𝐚 𝐏𝐚𝐫𝐚𝐝𝐢𝐬𝐞☀️ Escape to a luxurious tropical retreat near Florida’s best beaches, attractions, shopping, and dining. Perfect for family vacations, trips, or relaxing getaways, offers comfort, style, and the ideal location for an unforgettable stay. 📍Prime Location: ~ 5 mins to shopping & restaurants ~ 15 mins to Gulf beaches ~ 20 mins to Clearwater ~ 25 mins to Downtown St. Pete ~ 30 mins to Tampa International Airport

A welcoming backyard features a large pool surrounded by tropical landscaping and a privacy fence. Colorful pool toys, including a unicorn float, are visible on the water. Strings of lights illuminate the area, enhancing the serene atmosphere of the outdoor space.

4.9 out of 5 average rating, 187 reviews

The Oasis - Arcades - Golf & Games - Firepit

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

4.93 out of 5 average rating, 203 reviews

The Palm House | Free Heated Pool!

Come enjoy our newly renovated pool! Our updated home is ideally situated just a few minutes from local beaches, restaurants, and entertainment, making it a perfect home base for your Florida visit. The backyard boasts a newly renovated heated pool, outdoor shower and screened patio. Our bright living room offers a comfortable space to unwind after a long day, and our kitchen is fully stocked with cookware, utensils and a coffee station for your convenience. Updated pool pics coming soon!

5 out of 5 average rating, 127 reviews

Guest suite in Largo

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

5 out of 5 average rating, 214 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

4.94 out of 5 average rating, 146 reviews

Home in Seminole

Heated Pool no xtra chrge/Hot Tub 0.7 mi to Beach

Welcome to our beach house! - Prime location! 0.7 miles to Indian Shores - Heated pool at no extra charge - Hot tub, saltwater pool, mural for photos and outdoor shower -Family friendly (pack and play, booster seat and kid friendly dishes) - Chef kitchen with double ovens -Beach essentials (beach chairs, wagon, toys and towels) - Quiet and safe neighborhood Beaches: - 2 min to Indian Shores & Redington Beaches - 10 min to Madeira & Indian Rocks - 20 min to Clearwater & St. Pete

4.98 out of 5 average rating, 107 reviews

A private heated pool is surrounded by wooden decking, offering lounge chairs for relaxation. An oversized umbrella provides shade, while tropical plants enhance the outdoor space. The rear of the house is visible, along with a patio door leading into the home.

Home in St. Petersburg

ST Urban Oasis heated pool

Located in unincorporated St. Pete, you can keep it simple at this peaceful and centrally-located oasis. Want to be near the city and beaches while having your own private backyard sanctuary? This is your place to enjoy it all. This home features two bedrooms, one bathroom, and a private heated pool. The backyard has been filled with beautiful large palms, bamboo, and other zen features to allow you and your family to enjoy a relaxing and easily accessible stay in beautiful St. Pete.

The image displays a collage of the Splash House. Upper left shows a cozy seating area with modern furnishings in light colors. Upper right features a bright bedroom with a spacious bed and decorative accents. Lower left highlights a tranquil pool area surrounded by a patio. Lower right showcases a bathroom with modern fixtures and a stylish double sink.

4.92 out of 5 average rating, 127 reviews

Splash House - Relaxation Haven/Private Pool

Cozy Home in Largo Florida just 10 minutes from Indian Rocks beach and about 15 min from Clearwater Beach. Take time to relax in the comfort of this vacation home and be at ease while you spend time with your family. Peaceful and centrally-located. There is no neighbor behind because it connects to the Pinellas trail which offers miles and miles of uninterrupted biking and running. There is a delicious restaurant just a few blocks away called Latin Bowl.

4.97 out of 5 average rating, 204 reviews

An inviting outdoor space features a swimming pool surrounded by a spacious patio. Colorful lounge chairs in turquoise and red are arranged under a shaded pergola. Lush palm trees enhance the tropical atmosphere, creating a private retreat for relaxation.

Home in Seminole

5 STAR! Hot Tub-freeHeated Pool 4BD/2Ba 2 King bed

PARADISE best describes this GORGEOUS newly renovated VACATION HOME!! 4 bed room 2 bath HEATED POOL and GIGANTIC HOT TUB! 7 miles to the many local sugar sand gulf beaches and 3/4 mile away from grocery stores , Local ER, MANY restaurants, banks and gas stations/ convenience stores, GOLF COURSE, hair and nail salons, Walmart . Swimming POOL IS HEATED FOR FREE 80-85 degrees from oct 15 - april 15 seasonally SUPER FAST WIFI 571 mbps

4.95 out of 5 average rating, 137 reviews

Home in Clearwater

Artsy oasis in Clearwater

This centrally-located Clearwater house is just a short drive to beaches, airports, Dunedin, and downtown Tampa. This single-family home has a private in-ground pool, screened in porch, pergola, fire table, outdoor shower, and a variety of flowering plants. There are 2 bedrooms and a bonus room. There is a queen bed in each bedroom, bunkbeds in the bonus room, and two queen sofa beds in the living room. Pet and family friendly.