Holiday rentals with a pool in Belleair Beach

4.97 out of 5 average rating, 135 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.

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

4.94 out of 5 average rating, 132 reviews

Tropical Beachfront Penthouse-Beach Cottages

Welcome to this spacious top floor oceanfront condo at the Beach Cottages in beautiful Indian Shores, between Clearwater & St Pete Beach on the crystal clear waters of the Gulf of America. This exquisite condo with magnificent oceanfront views is just fabulous! Great care is taken to ensure everything about this vacation home is remarkable & tastefully complimented with King & Queen size beds, full kitchen/dining/bar area, Free High WiFi, Premium TV, Garage Parking, Private Beach, Pool & Spa.

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.

4.97 out of 5 average rating, 112 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!

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.

4.92 out of 5 average rating, 109 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, covered dining, and relaxing hammock! You’ll love this quaint Belleair Bluffs neighborhood offering easy commute to St. Pete Clearwater and Tampa Airports, local hospitals, etc.

Apartment in Belleair Beach

4.81 out of 5 average rating, 121 reviews

Cozy Suite On The Beach - Heated Pool

We’re pleased to announce that our property is now open, fully operational, and in excellent condition following the recent hurricane. Book with confidence and enjoy! ☞ Free Parking ☞ Heated Pool ☞ Self-check-in We are located on the beach at 3200 Gulf Blvd, Belleair Beach. Features include a comfortable bedroom, free parking, and a heated pool. Essentials (linen, towels, toiletries) are provided at the start of your stay. We have no hidden fees or complicated checkout instructions.

Flat in Indian Rocks Beach

The shared resort-style backyard features a large heated pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a peaceful ambiance is created by the surrounding greenery. The inviting blue sky completes this outdoor relaxation area.

4.94 out of 5 average rating, 145 reviews

Starfish Wishes! 90° Heated Pool! Steps to beach!

COMPLETELY REMODELLED beachy 2 bedroom vacation rental! Located a very short one block walk down a palm tree lined path to the sugary sands of Indian Rocks Beach and across the street from a beautiful park! Out back, you will find a large HEATED pool (Currently 90°!) with plenty of lounge chairs, dining tables, a new Weber BBQ grill, fire pit, pool floats & more. To make your trip as easy as possible, we provide you with all your beach needs, towels, umbrella, beach chairs & more.

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

4.97 out of 5 average rating, 113 reviews

Relax in a Newly Renovated Beach Front Paradise

Immerse yourself in the stunning beauty of the Gulf Coast at this hidden gem, perfectly nestled in the charming Indian Shores. This property exudes a coastal ambiance, providing a tranquil sanctuary to bask in the sugar-white sands and sparkling turquoise waters. Beach chairs & towels are thoughtfully provided. All you need to bring is a swimsuit & toothbrush. Exciting updates include new furniture & bedding added in '25 as well as a beautifully renovated walk-in shower in '24.

Cottage in Indian Rocks Beach

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 202 reviews

Luxury Beach Cottage | Walk to Dining & Sunset

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

Apartment in Indian Rocks Beach

A spacious balcony is bordered by tall palm trees, offering a view of the calm Gulf of Mexico and white sand beach. The clear blue sky complements the serene ocean, creating a tranquil setting for relaxation.

4.89 out of 5 average rating, 101 reviews

Gulf-View 2BR/2BA Beach Condo!

This Indian Rocks Beach Gulf Front Hamilton House building is located directly on unique Clearwater- St.Pete white sand beach with private beach access and heated pool, washer and drier in the unit. Our 3rd floor 1100 sq. feet 2 bedroom condo #207 offers a spacious balcony bordered with palm trees with northerly nice side view of the Gulf of Mexico and white sand beach that goes on for miles. Two assigned parking spaces (one under the building and second uncovered).

4.95 out of 5 average rating, 104 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

UPDATE: This condo community was NOT affected by the hurricane. I am very fortunate. There was NO flooding or wind damage. Kick back and relax at this roomy 1 bed, 1 bath boho beach condo. This community offers a heated pool, bbq grills and reserved, onsite laundry and parking. Stroll down the sidewalk (half mile to beach) and take in the fresh, gulf breezes as you enjoy Indian Rocks Beach. Beautiful sunsets, amazing food and a calm, relaxing beach community awaits you!

A sandy beach is visible, featuring several blue umbrellas and lounge chairs arranged along the shoreline. Gentle waves can be seen in the calm water, while fluffy white clouds float in the blue sky above, creating a serene coastal atmosphere.

4.93 out of 5 average rating, 162 reviews

Booking for July. Direct beach front!

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

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, 147 reviews

Seasalt Breeze - Easy pool access, Free parking.

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

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private outdoor pool is surrounded by tropical landscaping, featuring palm trees and colorful plants. Several lounge chairs are positioned alongside the pool, and umbrellas provide shade for outdoor relaxation. The area is enclosed by a white fence, creating a serene atmosphere.

4.88 out of 5 average rating, 131 reviews

The Paradise Cove No. 2

A cozy open-concept living area features a spacious light-colored sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, positioned on a striped area rug. Elegant pendant lights hang above a large kitchen island with a granite countertop, contributing to a welcoming ambiance.

4.98 out of 5 average rating, 143 reviews

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

4.86 out of 5 average rating, 163 reviews

Home in Seminole

Pool•Hot Tub•Free EV Charger•5 Mins to Beaches

A spacious screened-in pool area is highlighted, featuring a clear blue pool surrounded by a patio with lounge chairs. A modern kitchen and living room are reflected through large glass doors, connecting indoor comfort to outdoor relaxation.

4.82 out of 5 average rating, 103 reviews

Sunshine, Beaches & Refreshing Pool/Screen Patio

4.95 out of 5 average rating, 108 reviews

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.

Home in Seminole

Splash House - Relaxation Haven/Private Pool

4.94 out of 5 average rating, 133 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

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, 130 reviews

Palm Paradise - Family Amenities+Central Location

4.93 out of 5 average rating, 166 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

Apartment 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*

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 )

4.9 out of 5 average rating, 221 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 !

4.98 out of 5 average rating, 99 reviews

Lovely Condo minutes from beach & King bed

A welcoming entrance to The Avalon features a landscaped roundabout with manicured greenery and vibrant flowering plants. A central fountain adds a serene element, while the building's architecture is framed by palm trees and blue skies.

4.94 out of 5 average rating, 93 reviews

Condo Conveniently located to Clearwater Beach

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

4.96 out of 5 average rating, 134 reviews

Bright and Spacious 1Bed/1Bath condo.

A cozy bedroom is illuminated by natural light streaming through large windows adorned with patterned curtains. A spacious bed is dressed with floral bedding, accompanied by decorative pillows. A bedside table holds a lamp, and a framed art piece enhances the calming atmosphere, with the pool view visible outside.

4.94 out of 5 average rating, 125 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

Apartment in St. Petersburg

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, 282 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Other holiday rentals with a pool

Home in Indian Rocks Beach

5 out of 5 average rating, 5 reviews

Hgtv Style Pool Home, Across the Street from Beach

5 out of 5 average rating, 29 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

Flat in Indian Rocks Beach

A modern kitchen features sleek stainless-steel appliances, including a refrigerator and microwave. A large quartz island with seating for four is illuminated by overhead pendant lighting, while ample cabinetry provides storage. Natural light streams through a window adorned with blinds, enhancing the clean design of the space.

5 out of 5 average rating, 3 reviews

Modern 1BR Suite w/ Parking & Pool | Walk to Beach

Flat in Indian Rocks Beach

The serene beachfront view captures the horizon where the ocean meets the sky at dusk. Soft waves gently roll onto the shore, while silhouetted figures are seen walking along the beach. The scene is framed by coastal vegetation and the faint glow of twilight.

4.76 out of 5 average rating, 91 reviews

Cozy Beach Bungalow With parking!

Home in Indian Rocks Beach

The exterior of a two-story coastal home is showcased, featuring a light blue facade and a staircase leading to the second level. A garage is situated on the ground level, and palm trees are present in the surrounding landscape, providing a tropical ambiance.

4.83 out of 5 average rating, 12 reviews

Indian Rocks Oasis – Renovated 2BR Beach Retreat

4.83 out of 5 average rating, 46 reviews

A modern kitchen features an expansive marble countertop with bar seating. Two pendant lights hang above, illuminating the space. Stainless steel appliances are seamlessly integrated, and a sliding glass door opens to a small balcony with outdoor seating for two.

Flat in Clearwater

Avalon Sun-kissed Boutique: Luxury-free parking

A spacious living area is showcased with a light blue sofa and tropical-themed accents. A smart TV is mounted on the wall, while large sliding glass doors lead to a private balcony, presenting panoramic views of the beachfront. Natural light fills the room through the sheer curtains.

4.96 out of 5 average rating, 24 reviews

Beachfront Condo in Indian Shores

A comfortable living area features a large sectional sofa adorned with decorative pillows. A mounted flat-screen TV displays a beach scene, while light-colored wooden paneling adds warmth. Natural light enters through sliding glass doors, which lead to a screened-in balcony, creating an inviting space.