Holiday rentals with a pool in Pinellas Park

4.98 out of 5 average rating, 185 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's w/ Sling & Roku. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Guesthouse in St. Petersburg

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.

4.9 out of 5 average rating, 142 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!

4.97 out of 5 average rating, 145 reviews

A cozy living area features a comfortable gray sofa and a blue accent chest. Large glass doors open to a balcony, showcasing water views. A ceiling fan provides a gentle breeze, while decorative elements like wall art and a rug add a touch of charm.

Condo in St. Petersburg

Waterfront condo w heated pool and hottub

Wake up to waterfront views! Sip morning coffee on 20-ft private balcony overlooking Boca Ciega Bay, watch dolphins, unwind in the heated pool & spa while taking in stunning sunsets. This quiet corner condo offers a serene escape minutes from Madeira Beach, St. Pete, and local attractions, perfect for couples or solo travelers. Highlights: • Direct waterfront views • Heated pool, hot tub • Nearby boat rentals, trails, & Madeira Beach • 5 mins to Gulf beaches + 15 mins to Downtown St. Pete

4.97 out of 5 average rating, 390 reviews

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

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.

4.95 out of 5 average rating, 266 reviews

A private balcony offers a serene view of the bay, framed by lush palm trees. A glass table and two chairs are positioned for easy enjoyment of the surroundings, while the sparkling water glimmers under a clear blue sky.

Condo in St. Petersburg

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

Wake up to bay breezes in our fully updated 1-bed condo just a quick drive from the sand. Enjoy a sparkling heated pool, soothing hot tub, free parking & blazing-fast Wi-Fi. Inside you’ll find a full kitchen, king bed, 2 smart TV's & a large private balcony for sunset vibes. See dolphins while sipping morning coffee. A 6-min drive to renowned Madeira Beach. Laundry in the unit, and & a gym on site. Superhost service—fast replies & local tips. Book now for an unforgettable coastal escape!

4.91 out of 5 average rating, 403 reviews

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

Home in St. Petersburg

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Vibrant 2BR/1Bath home sleeps 8 guests with a magical outdoor space designed to create beautiful memories! A tropical saltwater pool and large covered entertainment area complete with a TV—perfect for relaxing and enjoying a cocktail. The interior is colorfully curated to embody the essence of a vacation! Located just 5 minutes from the beach and 25 minutes to downtown. We have 16 Airbnb homes (family-owned and operated), and we're dedicated to finding the perfect fit for your getaway.

Guest suite in St. Petersburg

A spacious patio area surrounds a clear swimming pool, framed by lush tropical plants. Two lounge chairs are positioned under a shaded umbrella, with a bike resting in the background. A barbecue grill is visible near the covered seating area, creating an inviting outdoor space.

4.98 out of 5 average rating, 372 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.

4.98 out of 5 average rating, 278 reviews

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.

Condo in St. Petersburg

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.

4.9 out of 5 average rating, 117 reviews

Villa in Largo

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

The exterior of the single-family home showcases a well-maintained facade, complemented by lush tropical landscaping. A spacious driveway leads to a garage, while a private, fenced yard is visible beyond. Large windows allow natural light to brighten the interior, set against a clear blue sky.

4.88 out of 5 average rating, 114 reviews

Tropical Pool Resort– Close to Beach, Lake, Golf

Relax in this spacious 4BR pool home near Florida’s sandy beaches & Lake Seminole Park! Safe and Ready! Enjoy a private fenced yard and pool, tropical landscaping, and plenty of space for family, work, or play. Just minutes to golf, tennis, dining & top attractions. Perfect for vacations, snowbirds, or remote work with 2 desks, a stocked kitchen & fun extras like bikes, beach gear & fitness space. Ask about special promotions then book your tropical retreat today!

4.98 out of 5 average rating, 145 reviews

A spacious living area features a sectional couch and a decorative area rug, enhancing the inviting ambiance. A dining table with modern chairs is positioned against a striking patterned accent wall, while natural light filters through the nearby windows, casting a warm glow over the space.

Home in Pinellas Park

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Looking for a place the whole family/group can enjoy? This centrally located MODERN house is not only full of fun and style but equipped with everything you could need. Think of it as your true home away from home. Guests will love the Instaworthy Retreat with features like 5 hole mini golf, giant outdoor games, a heated pool, 5000 arcade games and of course, photo ops. Located 6 miles to the beach or Downtown St. Pete this home is the perfect place to getaway.

4.98 out of 5 average rating, 242 reviews

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

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

UPDATED modern Light and bright colorful condo w 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/rest

Popular amenities for Pinellas Park rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 161 reviews

A cozy outdoor fire-pit area is surrounded by colorful seating. Decorative stones cover the ground, leading to a grill and the inviting glow of flames. A pool and shaded area can be seen in the background, set against a twilight sky.

Home in Clearwater

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

A spacious screened-in patio features a heated pool surrounded by sun loungers and a basketball hoop. A dining area with a table and chairs overlooks the pool. Clear blue skies and sunlight reflect on the water, creating a bright and inviting outdoor space.

4.93 out of 5 average rating, 46 reviews

Beautiful Family Pool House * Heated Pool *

5 out of 5 average rating, 10 reviews

A contemporary home is presented with a light-colored exterior and a stylish wooden garage door. Lush greenery and palm trees enhance the landscape. A spacious driveway leads to the entrance, framed by well-maintained flower beds and tropical plants under a clear blue sky.

Home in St. Petersburg

Paradise Palms - Private Pool Oasis - St. Pete

A dining area features a large wooden table set with white plates and woven placemats. Natural light fills the space from nearby windows, highlighting a modern kitchen in the background with white cabinetry and stainless steel appliances.

4.97 out of 5 average rating, 29 reviews

Fire Pit, Close to Beach, Shopping & Dining

5 out of 5 average rating, 7 reviews

Lost In Paradise - Heated Pool, Spa, MiniGolf

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.

4.95 out of 5 average rating, 120 reviews

Palm Paradise - Family Amenities+Central Location

4.94 out of 5 average rating, 138 reviews

A spacious outdoor area surrounded by lush greenery showcases a seasonally heated pool. Comfortable sectional seating is arranged around a glass table, complemented by large sun umbrellas. A BBQ grill and outdoor dining table are visible, creating an inviting space for relaxation.

Home in Clearwater

Palms and Dreams Villa 3/2 Heated Pool•BEACH 5 mi

An outdoor seating area features colorful bean bag chairs and sofas arranged around a modern fire pit. Two blue and white umbrellas offer shade, while a vibrant sunset sky creates a warm ambiance. Paved stone flooring surrounds the seating arrangement, enhancing the outdoor experience.

5 out of 5 average rating, 27 reviews

NEW! Coastal Pop • Karaoke-Spa-Pool-Sauna & More

Condo rentals with a pool

4.99 out of 5 average rating, 141 reviews

A well-appointed bedroom features a spacious queen bed with a striped blanket. Two bedside tables with lamps are positioned on either side. Natural light fills the room through a window adorned with light curtains, while tasteful artwork hangs on the concrete wall.

Condo in Clearwater

Seasalt Breeze, by the pool, NO PETS

4.99 out of 5 average rating, 213 reviews

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

Condo in Madeira Beach

Lux Condo w/ 2 balconies, Ocean & Marina views

4.89 out of 5 average rating, 219 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Condo in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

4.86 out of 5 average rating, 352 reviews

An inviting courtyard area is showcased, featuring a sparkling heated pool surrounded by lounge chairs. Lush greenery and well-maintained gardens add a natural touch, while the two-story yellow building encloses the area, creating a serene and communal atmosphere for relaxation.

Condo in Redington Beach

Royal Orleans at Redington Beach ( Studio )

4.88 out of 5 average rating, 114 reviews

The balcony area features a pair of sleek white chairs alongside a blue upholstered chair, offering a relaxing space to enjoy coastal views. Glass railings provide an unobstructed sightline to the sandy beach and the shimmering water under a clear blue sky.

Condo in Treasure Island

New Beachfront Resort Condo in Paradise

4.93 out of 5 average rating, 115 reviews

An aerial view presents a vibrant community with a central pool area surrounded by lounge chairs. Nearby, tennis courts and landscaped green spaces enhance the outdoor environment. The multiple buildings feature warm-colored exteriors with tiled roofs, creating a harmonious residential atmosphere.

Condo in Seminole

Two Bedroom Pool View Condo in Seminole

4.96 out of 5 average rating, 103 reviews

A heated swimming pool is surrounded by neatly arranged loungers, with palm trees providing shade. A clear sky and vibrant sunset colors reflect on the water's surface. The pool area is enclosed by a black fence, ensuring a private and relaxing environment.

Condo in Largo

Boho Beach Condo

Superhost

Condo in Clearwater

4.81 out of 5 average rating, 164 reviews

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

Other holiday rentals with a pool

Apartment in St. Petersburg

4.97 out of 5 average rating, 29 reviews

Bayview Balcony Condo, Hot Tub, Heated Pool, Bar!

5 out of 5 average rating, 9 reviews

Condo in Isla del Sol

Brand New condo with water views, Pool/Beaches

A circular arrangement of six turquoise Adirondack chairs surrounds a central fire pit, which is built from stone. The area is laid out with white gravel and bordered by lush greenery, including palm trees, offering a cozy setting for outdoor gatherings.

5 out of 5 average rating, 21 reviews

Largo Palms Duplex-2BR/2BA + Heated POOL Unit A

5 out of 5 average rating, 11 reviews

The outdoor area showcases a heated private pool surrounded by a stone patio. A cozy seating area is positioned under a covered porch. A giant ring toss game stands next to the pool, while lounge chairs and an umbrella provide options for relaxation.

Home in Pinellas Park

Coastin' Close Family Fun~HTD Pool~Outdoor Games

4.94 out of 5 average rating, 17 reviews

A modern kitchen features white cabinetry and a teal tiled backsplash. Three bar stools are arranged at the island, with stainless steel appliances visible. A cozy armchair with a leaf pattern is positioned in the living area, while natural light illuminates the space.

Home in St. Petersburg

NEW Private Pool Close to Madeira Beach Golf Cart

4.93 out of 5 average rating, 45 reviews

A private backyard pool oasis is shown, featuring a curvy, light blue pool surrounded by concrete decking. Lush greenery and a wooden fence provide privacy, while a small blue shed and a wooden structure with a roof are visible in the background.

Home in Pinellas Park

Backyard Pool Oasis | Minutes To Beach

Guesthouse in Historic Kenwood

A serene outdoor space features a curved pool surrounded by tropical plants. Lounge chairs are positioned near the water, alongside a shaded area with an umbrella. A guest house can be seen in the background, complementing the vibrant greenery and inviting setting.

5 out of 5 average rating, 66 reviews

Kenwood Cottage

A hot tub is seen in the foreground, with bubbling water reflecting sunlight. In the background, a spacious outdoor dining area and lounge seating are visible under a shaded porch. Lush greenery and potted plants enhance the inviting outdoor space.