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

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.

4.9 out of 5 average rating, 121 reviews

Relax in Family-Friendly comfort at Octopus Garden

Outdoor Paradise Private 10,000-gallon PebbleTec pool (up to 8 ft deep) Cantina bar for poolside refreshments Teak lounge seating & chaise chairs Weber propane grill + rolling cooler Resort-style umbrellas & lush landscape for sun or shade Fully Equipped Kitchen Stainless steel appliances, cookware & utensils Coffee station fully stocked Air fryer + blender for smoothies & cocktails Unique Octopus Garden dining area Living Room Large ultra-comfy sectional 70” Samsung Smart TV Boa

Guest house 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!

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.

4.97 out of 5 average rating, 145 reviews

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.

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.

4.95 out of 5 average rating, 266 reviews

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!

4.97 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

Welcome to The Merry Mint! A family & pet friendly 2/1 oasis located 4mi from the #1 beach in America; Clearwater This colorful & whimsical property is just minutes from grocery, 5 star restaurants, & every convenience. Only a short drive to the beach! Or stay in & enjoy: ★ 24x12 Pool w/LED multicolor pool light ★ 34X18 Pool Deck ★ Loungers ★ 16x20 Grill Deck ★ Fire-Pit w/grill grate ★ Yard Games (regulation corn hole, jenga, connect four, etc) ★ BBQ Grill ★ string lights

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.

4.98 out of 5 average rating, 278 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.

4.9 out of 5 average rating, 113 reviews

A view of a heated saltwater pool is framed by two lounge chairs, positioned on a grassy area. Red umbrellas provide shade for seating areas, and a spacious patio can be seen in the background, featuring modern outdoor furniture and a neutral-colored house.

Home in Clearwater

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

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!

4.98 out of 5 average rating, 146 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.

A serene outdoor space features a heated saltwater pool surrounded by a screened enclosure. Lounge chairs are positioned poolside, and a children's swing set is visible in the background. The vibrant sunset creates a warm ambiance over the tranquil setting.

4.96 out of 5 average rating, 123 reviews

Tropical Palm Retreat | Pool & Games

Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

4.97 out of 5 average rating, 175 reviews

An open concept living area features a dining table set for four, surrounded by stylish chairs. The well-equipped kitchen, highlighted by modern appliances and a granite countertop, is visible in the background, alongside a cozy seating area with an electric fireplace and TV.

Apartment in Seminole

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

Amazing value 2 bedroom 1 bath condo! 2 miles to Indian Shores beach. Nicely Updated gated condo with gym, tennis courts, large pool and pet friendly! High ceilings! We have everything that you need for a comfy perfect vacation! Beautiful condo featuring granite counters, tile floors, nice tennis court / green scape view! King master bed,queen guest bedroom & queen sofa couch. Our condo is stocked with everything for a NICE VACATION!

Popular amenities for Pinellas Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A vibrant game room showcases a pool table in the center, surrounded by a striking light green grass wall and colorful decor. Comfortable seating is provided, with a smart TV mounted on the wall. A cozy seating area with decorative elements enhances the lively atmosphere.

4.81 out of 5 average rating, 133 reviews

Heated Pool, Fire Pit, Game Room | Tropic Vibes!

5 out of 5 average rating, 24 reviews

A newly renovated outdoor area features a tranquil swimming pool surrounded by stone tiles and lush tropical plants. The bright blue water reflects the sunny sky above, while a dining table is positioned nearby, enhancing the welcoming environment of the space.

Home in St. Petersburg

Modern Coastal Retreat

The screened-in pool area features a sparkling blue pool, with lounge chairs positioned nearby. The sky is painted in shades of pink and purple at dusk. The open patio provides views of the house's interior, enhancing the inviting ambiance.

4.95 out of 5 average rating, 60 reviews

The Pool House -Private Heated Pool w Entire House

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 *

A modern kitchen features sleek stainless-steel appliances and a spacious island with seating. The inviting living area showcases a large leather sectional and an entertainment center with a smart television. Natural light illuminates the space through wide windows, creating a bright and welcoming ambiance.

4.84 out of 5 average rating, 45 reviews

ONE PALM- Pool House Close to the Beach!

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 spacious pool area features a heated swimming pool surrounded by a lanai, offering protection from the elements. Colorful floats rest on the water's surface, and the sky showcases vibrant hues of sunset. A patio dining space and outdoor seating are visible beyond the pool.

4.98 out of 5 average rating, 102 reviews

[Top Pick] Family Fun Oasis | Heated Pool, Hot Tub

The living area displays a large sectional sofa facing a 65-inch TV, with a colorful wall mural and a dining space visible in the background. The game room features a pool table and a 65-inch TV, while the outdoor area showcases a heated pool surrounded by lounge chairs and umbrellas.

5 out of 5 average rating, 42 reviews

Lrg Heated Pool | Fire Pit | Game Rm | Family Fun

Apartment rentals with a pool

4.99 out of 5 average rating, 141 reviews

Apartment in Clearwater

Seasalt Breeze, by the pool, NO PETS

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.

Apartment in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

Apartment in Redington Beach

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.

4.86 out of 5 average rating, 352 reviews

Royal Orleans at Redington Beach ( Studio )

Apartment in Treasure Island

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.

4.88 out of 5 average rating, 114 reviews

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.

Apartment 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.

Apartment in Largo

Boho Beach Condo

A serene sunset over the intercoastal waterway is captured, with warm hues reflecting on the calm water. Lush palm fronds frame the scene, enhancing the tranquil atmosphere as the sun dips below the horizon.

4.94 out of 5 average rating, 218 reviews

Sea La Vie- Studio by the bay!

4.81 out of 5 average rating, 164 reviews

Apartment in Clearwater

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

Other holiday rentals with a pool

Apartment in Isla del Sol

5 out of 5 average rating, 9 reviews

Brand New condo with water views, Pool/Beaches

5 out of 5 average rating, 52 reviews

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

Apartment in Clearwater

Wonderful Condo at Avalon - Fully Renovated!

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

5 out of 5 average rating, 10 reviews

An open-concept living area features a modern dining table set for four. A spacious living room is visible with large windows allowing natural light, accompanied by a comfortable sectional sofa. A kitchen area can be seen in the background, showcasing wooden cabinetry and appliances.

Flat in Largo

Condo 3/2 With POOL.

Guest house 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

5 out of 5 average rating, 19 reviews

A private balcony overlooks tranquil waterfront views, featuring a round table surrounded by white wicker chairs. Lush greenery and palm trees frame the scene, while sunlight casts gentle shadows across the space, enhancing the connection to the serene outdoor environment.

Flat in St. Petersburg

Dolphin Views and Resort Pool!