Holiday rentals with a pool in Belleair Beach

4.98 out of 5 average rating, 205 reviews

Luxe BeachHouseB/Heated Pool/2 min Walk to Beach

Welcome to your home away from home.Sand, sun, and ocean breeze are waiting for you.Our modern Beach House is located 2 minutes walk from the beautiful and quiet beach with direct access. Our four story house has a private backyard,hot tub, heated pool rooftop and available GolfCart for a fee. We have everything that you need for bigger groups of families to relax on your vacation.Our BeachHouse B is in a quiet neighborhood and still a walking distance from restaurants bars and stores. BTR#2099

Apartment in Belleair Beach

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

4.71 out of 5 average rating, 519 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

No impact from hurricanes! - RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

Apartment in Madeira Beach

4.98 out of 5 average rating, 104 reviews

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

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.

4.83 out of 5 average rating, 364 reviews

Stunning views! Spot dolphins from the pool!

BTR#2114 This home has it ALL including incredible open water sunsets! Every detail has been carefully thought out and updated. This is a VERY upscale, coastal, single story waterfront home. A complete waterfront remodel w/ dock & pool that looks and feels like a new home w/ stunning water views from your own back patio! The water glistens and sparkles from 3 pm thru sunset and after, the sky is set on fire for 40 minutes. White sandy beach is only few blocks away! Amazing home inside & out!

A light blue living room features two armchairs and a sectional sofa, complemented by a white coffee table at the center. Large windows with blinds allow natural light to brighten the space, while a decorative throw and small lamp add subtle accents. A rug covers the floor.

4.92 out of 5 average rating, 104 reviews

The Shack at IRB

*FULLY REMODELED!!! *TOTALLY SMOKE- FREE *WALKABLE BEACH COMMUNITY *PERFECT FOR COUPLES Come enjoy our quiet 1 bedroom condo with a cozy living room, full kitchen and very close beach access!! All beach items provided! Short stride to the property’s private pool, and a public Trolley that runs daily between Clearwater & St Pete Beaches. Easy stroll to many nearby restaurants, bars & shops. Includes wifi, stream Tv service & private stacked laundry. A very peaceful spot for a beach getaway!

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, 210 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!

4.98 out of 5 average rating, 367 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

UTOPIA best describes this perfect single story VACATION HOME ! 5 MINUTE DRIVE TO BEACHES!! HUGE AMAZING RESORT SYTLE FREE HEATED POOL with LUXURIOUS PERGOLA, HOT TUB , TIKI BAR and plenty of outdoor seating perfect for soaking up the Florida sun ! Large 3 bedroom 3 bath pool home. Pool heat starts Oct 15 and runs thru april 15 seasonally for FREE( heats 80-85 degrees) large four person hot tub is hot and ready at 101° upon your arrival. No waiting on a hot tub to heat up!

The inviting living space is furnished with a blue sofa, two armchairs, and a white coffee table. A starfish-patterned rug adds a nautical touch. Natural light filters through window blinds, illuminating the area. The open layout connects to the kitchen, visible in the background.

4.97 out of 5 average rating, 133 reviews

Beach Across the St | No Stairs |Parking in Front!

Just 150 feet from the beach, this renovated 1 bedroom, 1 bath condo is the perfect coastal escape. Simply walk across the street to the beach, or explore several restaurants just a short stroll away. Enjoy parking directly in front of the unit and easy ground level access with no stairs. Inside, you’ll find a comfortable, welcoming space to relax after a day in the sun. Ideal for couples or solo travellers looking for convenience, comfort and an unbeatable beach location.

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.

4.89 out of 5 average rating, 158 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

Townhouse in Indian Rocks Beach

A comfortable living room features a dark sectional sofa adorned with vibrant Kraken-themed cushions. Warm light is provided by floor lamps on either side. Large sliding glass doors lead to a balcony with views. A dining area is visible, alongside a small kitchen with a bar.

4.94 out of 5 average rating, 108 reviews

The Kraken-6-pass golf cart! Plus Pool

The Kraken is new with tasteful Kraken decorations to pull the space together. Packed with a big 75" TV, big double queen guest room, and king sized master bedroom. The Kraken is the perfect beach house to get your toes in the water in minutes, the perfect beach community to walk to local cuisine, with the perfect creature comforts of home. The penthouse floor is for families/groups that want to have fun together with epic sunsets perfect for sun downers.

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

4.96 out of 5 average rating, 214 reviews

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

Apartment in Belleair Beach

4.84 out of 5 average rating, 107 reviews

Condo On The Beach - Heated Pool - Self Check-in

We’re happy to announce that our property is open, fully operational, and in excellent condition after the recent hurricane. Book with confidence and enjoy your Florida getaway! ☞ Free parking ☞ Heated Pool ☞ AC ☞ Self check-in ☞ Full Kitchen We are located on the beach at 3200 Gulf Blvd, Belleair Beach. Essentials (linen, towels, toiletries) are provided at the start of your stay. We have no hidden fees or complicated checkout instructions.

Popular amenities for Belleair Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A four-person outdoor dining table is set with plates and glasses of red wine, overlooking the waterway. A double kayak is visible on the shore, and boats are docked in the background under a blue sky with a few clouds.

4.94 out of 5 average rating, 71 reviews

Waterfront | King Bds | Htd Pool | BBQ | 2 Kayaks

The outdoor space features a heated pool surrounded by a tiled patio. Three lounge chairs offer a place to relax under a large umbrella. A whimsical pool float adds a playful touch. A colorful mural of tropical leaves is visible on the exterior wall.

4.97 out of 5 average rating, 35 reviews

Muse by the Shore

An outdoor seating area is illuminated by string lights, featuring a table with a fire pit at its center. Two wine glasses filled with red wine are positioned next to a bottle of wine. Nearby, two red cups and several beer bottles add to the relaxed atmosphere.

4.96 out of 5 average rating, 178 reviews

Cozy Stylish Home w/ Heated Pool & Big Parking

5 out of 5 average rating, 206 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 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, 155 reviews

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

4.99 out of 5 average rating, 101 reviews

Beach, golf cart, pool and pickleball at Oasis

4.94 out of 5 average rating, 145 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

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.

4.93 out of 5 average rating, 121 reviews

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

Apartment rentals with a pool

Apartment in Independence Square

4.91 out of 5 average rating, 131 reviews

Oceanfront View, Spacious Townhouse, Heated Pool

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.

4.98 out of 5 average rating, 120 reviews

Relax in a Newly Renovated Beach Front Paradise

4.96 out of 5 average rating, 164 reviews

Good Times and Tan Lines @ #105intercoastal

4.98 out of 5 average rating, 162 reviews

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.

Apartment in Clearwater

Ocean Breeze • Easy - Heated Pool Access

A bright living room features large sliding glass doors revealing a scenic water view. Comfortable blue sofas are arranged around a coffee table, complemented by a TV console and accent chairs. Light-colored walls and ceiling fan contribute to the spacious feel of the area.

4.98 out of 5 average rating, 113 reviews

Captain's Cove Waterside Condo 103 We are open!

A bright living space features a light blue wall adorned with crab artwork. A wooden dining table is surrounded by bench seating, while a cozy seating area includes a grey sofa and colorful area rug. Natural light fills the room through nearby windows.

4.97 out of 5 average rating, 38 reviews

Direct Beach Access, Heated Pool, Restaurants!

A view of the heated Gulf-side pool is presented, surrounded by lounge chairs under a clear blue sky. The corner penthouse is highlighted above the pool area, illustrating the building's multi-level design. Guests can be seen enjoying the pool and relaxing in a tranquil setting.

4.85 out of 5 average rating, 39 reviews

Sea Isles Unit P Top Floor Mid April Deals!

A cozy living area is furnished with a light brown sofa adorned with colorful throw pillows. A wooden coffee table sits atop a patterned area rug with floral designs. A large television is mounted on the wall, and a kitchen area is visible in the background.

4.93 out of 5 average rating, 103 reviews

Coastal Condo with Pool Near Beach & Intracoastal

Other holiday rentals with a pool

Apartment in Redington Shores

A bright living area features large windows offering sweeping ocean views. A sleek white sectional sofa sits atop a soft area rug, accompanied by a stylish coffee table set with glasses and a bottle. A flat-screen television is mounted above an electric fireplace, adding comfort to the space.

4.98 out of 5 average rating, 62 reviews

May 28-June 6 Avail! Beachfront 2/2 w/Jacuzzi & FP

Cottage in Indian Rocks Beach

A sandy pathway leads through lush greenery, flanked by palm trees, towards the beach. A sign displaying beach access information stands on the left. Benches provide seating along the path, with views of the water visible in the distance under a partly cloudy sky.

4.94 out of 5 average rating, 35 reviews

Seaside Retreat Cottages #4

4.89 out of 5 average rating, 9 reviews

A spacious pool area is surrounded by palm trees and lounge chairs, offering a vibrant atmosphere. Umbrellas are positioned for shade, and a view of the beach is visible in the background, enhancing the relaxing setting.

Apartment in Clearwater

Two Bedroom Deluxe, Clearwater A400

5 out of 5 average rating, 12 reviews

Home in Palm Harbor

Honeymoon Luxury Residence with Heated Pool &Sauna

5 out of 5 average rating, 11 reviews

Home in Seminole

Heated Pool•Gym•Sauna•Hot Tub•Fire Pit & 7 Beds!

5 out of 5 average rating, 7 reviews

Home in St. Petersburg

Waterfront, Pool & Dock | Bayfront Oasis

A spacious corner balcony features a new couch and a comfy chair, offering an unobstructed view of the ocean. A heated pool is visible below, surrounded by palm trees and beach chairs, enhancing the inviting outdoor space.

4.92 out of 5 average rating, 26 reviews

Oceanfront, Huge Balcony, HeatedPool,2King bedroom

A living area features a brown leather sofa adorned with a decorative pillow. A round coffee table is positioned in front of the sofa, while a fully equipped kitchen with white cabinetry and stainless steel appliances is visible in the background. Two bar stools sit at the kitchen counter.