Holiday rentals with a pool in Harbor Bluffs

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 !

This condo is a true gem, conveniently situated only a 6 minute drive away from highly-rated Indian Rocks Beach, celebrated by TripAdvisor. You'll be pleased to know that there's a beautiful golf course just a few minutes drive. Situated on the first floor , this modern condo features a screened patio with views of serene fountain. The complex offers a pool, gas BBQ for grilling and free parking. Plus, it is ideally located near everything you need, including a Starbucks just a short drive away

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, 102 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.

Superhost

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.

Home in Seminole

4.9 out of 5 average rating, 122 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

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 280 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

4.91 out of 5 average rating, 323 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.

The outdoor space features a heated pool surrounded by a spacious patio. The clear blue water reflects the sky, with palm trees providing shade nearby. Lounge chairs are placed around the pool for relaxing in the sun.

4.95 out of 5 average rating, 121 reviews

Largo Poolside Paradise Heated Pool 10Min To Beach

Escape to this stunning heated pool home in Largo, just 10 minutes from Florida’s top beaches! Relax in your private outdoor oasis featuring a large sectional, smart TV, fire pit, BBQ grill, and alfresco dining for six. Enjoy loungers, a daybed, and a large putting green with putters and golf balls. FREE beach chairs and umbrellas are included for your convenience. Book now for the ultimate getaway in Largo, and make memories that last a lifetime! Perfect for relaxation and fun under the sun.

Bungalow in Indian Rocks Beach

4.96 out of 5 average rating, 198 reviews

Your private Waterfront Pool home!

See photos for City holiday event dates! Boat parade ! Street parade! Tree lighting! 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

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

** This house has no checkout requirements - just take your belongings and close the door on your checkout day. ** Experience the ultimate beach vacation in our stunning 3BR home, boasting a brand-new (Jun 2023), upscale pool for leisurely days under the sun and huge in-ground hot tub for relaxing evenings. The fully-equipped kitchen, thoughtfully arranged, provides all modern amenities. Each bedroom, with its plush bedding, is perfect for relaxation after a day’s activities.

Superhost

Condo in Belleair Beach

4.8 out of 5 average rating, 105 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! ☞ Beachfront ☞ Free parking ☞ 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.

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, 166 reviews

Cozy Stylish Home w/ Heated Pool & Big Parking

Welcome to Your Cozy & Stylish Home with Heated Pool + Big Parking! Our newly renovated house combines modern style and cozy comfort with rare amenities you’ll love – a heated private pool and a large parking area for up to 8 cars or even an RV. Perfect for a family trip, a friends’ getaway, a work retreat, or just a relaxing stop on your road adventure – this home is designed to make every stay easy and enjoyable!

4.94 out of 5 average rating, 129 reviews

Swim-Out Bedroom, Waterfall pool! The Peace Place

Unique tropical oasis complete with swim out bedroom and tiki bar! LGBTQIA + welcome! Hablo Español. Pet haven. Tropical Airbnb retreat! Our unique resort-style heated PRIVATE pool with waterfalls and dual sun-shelves, / in pool loungers, surrounded by lush landscaping, is a private oasis. 3 bedrooms, with Large 3rd bedroom with 2 queen beds Rental beach truck available at the home when you arrive. Inquire.

4.97 out of 5 average rating, 115 reviews

A modern kitchen is showcased with stainless steel appliances and a central island featuring bar seating. Sleek cabinetry and a bright light fixture enhance the space. Natural light fills the room, emphasizing the clean lines and functional design.

Condo in Clearwater

Clearwater Retreat • Gated Community + Heated Pool

✨ Welcome to your Cozy Clearwater Retreat! This modern 1-bedroom condo in The Avalon gated community offers comfort and convenience just minutes from Clearwater Beach. Enjoy vaulted ceilings, an open layout, in-unit laundry, fast WiFi, and a screened patio. Guests love the clean space, safe location, and the resort-style pool just steps away—perfect for couples, solo travelers, or small families.

Popular amenities for Harbor Bluffs rentals with a pool

Kitchen

Wi-Fi

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, 128 reviews

The Paradise Cove No. 2

Home in Indian Rocks Beach

The outdoor area features a heated saltwater pool illuminated with a soothing blue hue. Surrounding palm trees and tropical landscaping enhance the tranquil atmosphere. A yellow and white striped umbrella provides shade beside the pool, offering a picturesque view of the waterway beyond.

4.91 out of 5 average rating, 88 reviews

OceanView~Golf Cart~Heated Pool~5k SqFt~Game Room

A sparkling pool sits in the center of a landscaped outdoor area, surrounded by comfortable lounge chairs and umbrellas. Adjacent to the pool, a covered patio offers a dining area, while a well-maintained lawn with vibrant greenery enhances the inviting atmosphere.

5 out of 5 average rating, 24 reviews

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

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 151 reviews

Palm Oasis | Heated Pool | Near Beaches

4.97 out of 5 average rating, 198 reviews

A vibrant pool area is framed by a thatched-roof tiki hut, providing shade over a set of outdoor seating. A saltwater pool glistens in inviting blue, surrounded by tropical landscaping. Colorful adirondack chairs are arranged neatly along the edge, enhancing the outdoor atmosphere.

Home in St. Petersburg

Beach Vacation Dream Pool Home-5 Mins to Beach

4.95 out of 5 average rating, 104 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

4.99 out of 5 average rating, 339 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

4.98 out of 5 average rating, 47 reviews

Bay Breeze - King Beds | Golf | Htd. Pool | Arcade

Condo rentals with a pool

4.99 out of 5 average rating, 110 reviews

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.

Condo in Indian Shores

Blue Sea Renity -Steps to Beach| Heated Pool

4.82 out of 5 average rating, 120 reviews

The living room features a spacious sectional sofa in soft blue, complemented by decorative pillows. A large flat-screen TV is mounted on a textured wall, while a coffee table is centered in the area. A wall art piece depicting ocean waves enhances the coastal theme.

Condo in Clearwater

Seaside Paradise at Clearwater - Resort Style

Condo in Indian Rocks Beach

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, 128 reviews

Renovated Condo! Across the Street 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 )

4.93 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

Condo in Indian Rocks Beach

A comfortable living area is presented with a spacious sectional sofa adorned with decorative pillows. A large flat-screen TV is mounted on a wooden accent wall, enhancing the cozy atmosphere. The open layout leads towards a bright kitchen visible in the background.

4.94 out of 5 average rating, 113 reviews

Golf Cart, 2 bed 2 Bath, Heated Pool

Condo in Clearwater Beach

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 305 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

4.98 out of 5 average rating, 142 reviews

The bedroom features a spacious bed adorned with patterned pillows, complemented by two bedside tables with decorative lamps. Artistic wall frames in muted tones enhance the ambiance. A soft glow is provided by lighting, and sheer curtains allow natural light to filter in.

Condo in Clearwater

Cozy condo, main floor, min to beach, heated pool

Other holiday rentals with a pool

Villa in Indian Rocks Beach

An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.

5 out of 5 average rating, 39 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

Home in Indian Rocks Beach

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.

5 out of 5 average rating, 23 reviews

Muse by the Shore

4.87 out of 5 average rating, 60 reviews

A cozy dining area is positioned next to expansive glass windows offering a view of the ocean. A round table with two white chairs is complemented by rustic decor, while light-colored curtains frame the scene, enhancing the openness and connection to the seaside.

Condo in Belleair Beach

Belleair Beach 215 Beachfront Gem Steps from Sand

4.87 out of 5 average rating, 46 reviews

Lush gardens are featured at this tranquil property, with vibrant greenery and colorful plants surrounding a spacious lawn. The building’s screened-in balconies are visible among trees, creating a serene atmosphere just steps away from the outdoor area.

Condo in Largo

Comfortable 2 Br/2 Bath condo

Home in Indian Rocks Beach

5 out of 5 average rating, 12 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

5 out of 5 average rating, 10 reviews

Condo in Belleair Beach

Sonrisa 1 - | Beachfront Condo in Belleair Beach

Aerial view of the property highlights a private dock with a kayak, surrounded by lush tropical landscaping. A tiki dining hut is situated on the spacious lawn, providing a serene outdoor space. The waterway can be seen flowing alongside the home, enhancing the natural setting.

5 out of 5 average rating, 50 reviews

Manatee Cove Waterfront • Heated Pool, Dock, Kayak

A private pool area features a clear blue pool surrounded by lush greenery and palm trees. Two lounge chairs are positioned beside the pool, and a shaded seating area is visible in the background. A splash pad adds a playful element to the outdoor space.