Holiday rentals with a pool in Belleair Beach

The backyard features an inground pool surrounded by a smooth deck, with lounge chairs positioned beside it. Lush greenery and palm trees are seen throughout the space, enhancing the outdoor living area. A covered pergola provides shade, and a grassy area is included for relaxation.

4.91 out of 5 average rating, 104 reviews

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

Welcome to BELLEAIR BEACH OASIS! This luxuriously updated 2BR/1BA POOL HOME is minutes away from beaches and golf courses! Walking distance to Belleair grocery, coffee shops, restaurants and more. Enjoy the private and fully fenced resort-style outdoor living featuring: inground pool, modern pergola w/lounge chairs, grill, covered dining and relaxing hammock! You’ll love this quiet Belleair Bluffs neighborhood offering easy commute to St. Pete Clearwater and Tampa Airports, local hospitals, etc.

4.97 out of 5 average rating, 134 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

4.91 out of 5 average rating, 324 reviews

A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.

Guest suite in Largo

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

4.97 out of 5 average rating, 148 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

For lease, Navidad! Waterfront condo gorgeous view

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

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

4.99 out of 5 average rating, 110 reviews

Blue Sea Renity -Steps to Beach| Heated Pool

Welcome to Blue Sea Renity — your peaceful 1-BR beach retreat just 2 minutes from the sand in Indian Shores, Florida. With a heated pool, free on-site parking, and a full complement of beach gear (chairs, cooler, umbrella, cart) — everything you need for a relaxing Gulf-coast stay is right here. Designed for solo travelers, couples, small families, or remote-work getaways, our condo blends modern comfort with true beachside ease. Browse the photos, pick your dates, and let the vacation begin!

A beachfront balcony features a round table with four striped chairs, inviting outdoor relaxation. The expansive view showcases sandy shores meeting the calm turquoise waters under a clear blue sky. Sliding glass doors provide easy access to the living space.

4.99 out of 5 average rating, 116 reviews

Five Star Beachfront Condo Newly Renovated

A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

Apartment in Indian Rocks Beach

A heated pool area features a curved blue swimming pool surrounded by a stone deck. Several lounge chairs are positioned around the pool, and umbrellas provide shade. Lush palm trees are visible in the background, contributing to the relaxed atmosphere.

4.94 out of 5 average rating, 142 reviews

Coral Reef~90° Heated Pool~Remodeled~2 min 2 beach

LOCATION! LOCATION! LOCATION! Completely renovated vacation rental located 1.5 blocks to the beautiful beach & across the street from Brown Park. This unit is located on the 2nd floor of a small two story building w/ 4 units. Out back is a large HEATED pool, lounge chairs, a dining table, grill, surfboard shower, fire pit and more. Walk two minutes down a beautiful palm tree lined path to the beach! We provide you w/ all your beach needs, towels, umbrella, beach chairs, floats and much more!

Bungalow in Indian Shores

A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.

4.96 out of 5 average rating, 174 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

Cottage in Indian Rocks Beach

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

4.96 out of 5 average rating, 167 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

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

Apartment in Indian Rocks Beach

A heated pool is surrounded by palm trees, with two blue sunshelf loungers partially submerged in the water. Spacious chaise loungers are positioned around the pool area, featuring a light-colored stone deck and privacy provided by a wooden fence in the background.

4.97 out of 5 average rating, 151 reviews

Triplex- heated pool, bikes, walk to beach,

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

Bungalow in Indian Rocks Beach

A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.

4.9 out of 5 average rating, 144 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

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.

4.99 out of 5 average rating, 145 reviews

Seasalt Breeze, by the pool, NO hidden fees

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

Popular amenities for Belleair Beach rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.91 out of 5 average rating, 113 reviews

Heated Pool and Spa | 5 min to beach

A private in-ground pool is surrounded by lush landscaping, featuring a unique unicorn float. A shaded umbrella stands nearby, offering a cozy spot to relax while enjoying the tranquil outdoor setting.

4.95 out of 5 average rating, 167 reviews

Cozy Stylish Home w/ Heated Pool & Big Parking

The pool area features a heated pool surrounded by a screened enclosure. A hot tub is positioned nearby, with modern chaise lounges and a dining table with chairs offering ample seating for relaxation. Lush greenery is visible beyond the enclosure, enhancing the space.

4.86 out of 5 average rating, 207 reviews

Beautiful Heated Pool and Hot Tub Oasis*Near Beach

4.96 out of 5 average rating, 127 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

5 out of 5 average rating, 180 reviews

Piece of paradise in Indian Rocks Beach.

The outdoor pool, surrounded by palm trees, reflects the clear blue sky. Comfortable loungers are placed nearby, offering ample space for relaxation. The glistening water leads to views of the waterfront, enhancing the serene atmosphere of the outdoor environment.

4.84 out of 5 average rating, 355 reviews

Stunning views! Spot dolphins from the pool!

4.99 out of 5 average rating, 341 reviews

A spacious outdoor pool area is visible, featuring a large swimming pool surrounded by lounge chairs and seating areas. A pergola provides shade, while decorative planters add greenery. The area is enclosed by a privacy fence, creating a secluded retreat.

Home in Seminole

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

A shaded outdoor space features two hanging egg chairs and a wooden coffee table, surrounded by a striped rug. A comfortable seating area with a love seat and additional chairs faces the pool, while large glass doors provide access to the interior.

4.95 out of 5 average rating, 125 reviews

Palm Paradise - Family Amenities+Central Location

Condo rentals with a pool

An aerial view captures the vibrant community pool surrounded by palm trees, with the serene blue waters of the Gulf in the background. The layout of the condo complex is visible, showcasing its proximity to the beach and inviting outdoor spaces.

4.96 out of 5 average rating, 145 reviews

Serenity by the Sea * Steps to the Ocean*

A spacious balcony features two chairs and a round table, providing a stunning view of the Gulf. The horizon shows a clear sky above the tranquil water, with sunbathers visible along the beach. Lush greenery and a palm tree are seen framing the scene.

4.92 out of 5 average rating, 145 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

4.9 out of 5 average rating, 220 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 !

4.98 out of 5 average rating, 98 reviews

Lovely Condo minutes from beach & King bed

4.96 out of 5 average rating, 52 reviews

Renovated, free Parking only 10 min to the beach

Condo in Indian Rocks Beach

A spacious living room features a large sectional sofa adorned with decorative cushions, providing a comfortable seating area. A coffee table with a natural wood finish is central to the room. Sliding glass doors open to a balcony, revealing views of the beach and ocean.

5 out of 5 average rating, 100 reviews

Beach Days & Family Fun - Last Minute Openings

4.87 out of 5 average rating, 171 reviews

The image shows a heated pool surrounded by a patio area with lounge chairs. Palm trees provide shade, and the two-story building encircling the pool features balconies. Well-maintained landscaping adds greenery to the setting, creating a peaceful atmosphere.

Condo in Redington Beach

Royal Orleans at Redington Beach ( Studio 203 )

4.98 out of 5 average rating, 279 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

Other holiday rentals with a pool

The living area is furnished with a light-toned sectional sofa, accompanied by a side chair. A round dining table for four is visible, along with a modern kitchen behind it. Decorative plants and a media console add a touch of greenery and organization to the space.

4.91 out of 5 average rating, 68 reviews

Chateaux Beachfront Condo/Top Unit - Indian Shores

Condo in Indian Rocks Beach

5 out of 5 average rating, 15 reviews

Ocean Way 204 Beach Front

4.96 out of 5 average rating, 49 reviews

An outdoor view reveals a large heated pool surrounded by lush landscaping and palm trees. Lounge chairs are positioned around the pool, with a barbecue area visible to the left. The elegant architecture of the nearby building adds to the inviting community ambiance.

Apartment in Clearwater

Avalon. Clearwater. Cozy condo. Pool view.

A bedroom featuring a spacious bed adorned with a floral-patterned duvet and an assortment of blue and white pillows. Flanking the bed are two bedside tables with lamps, and decorative wall art displaying the names of nearby locations. Dark curtains frame the window.

4.93 out of 5 average rating, 14 reviews

Stylish NEW one bedroom condo Clearwater beach

5 out of 5 average rating, 14 reviews

The pool area features a spacious outdoor space surrounded by lounge chairs. Clear waters create a relaxing atmosphere, while palm trees provide shade. In the background, a beautifully designed building with multiple windows complements the inviting space.

Apartment in Clearwater

Awesome Condo in Clearwater, FL

5 out of 5 average rating, 12 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

A private balcony extends over the beach, featuring a round table with four chairs and two lounge chairs. The view showcases the serene Gulf of Mexico, where soft waves meet a sandy shore under a bright blue sky.

4.82 out of 5 average rating, 60 reviews

180 Degree Gulfview from the Balcony w/Lovely Pool