Holiday rentals with a pool in Bay Pines

4.94 out of 5 average rating, 127 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

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

A screened-in pool area features a uniquely shaped pool with clear blue water, inviting relaxation. Sunlight filters through the mesh covering, illuminating the surrounding patio. Lush greenery lines the background, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 163 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you enjoy a pool heated to 86 degrees for free! Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

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, 265 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!

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

4.91 out of 5 average rating, 402 reviews

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Vibrant 2BR/1Bath home sleeps 8 guests with a magical outdoor space designed to create beautiful memories! A tropical saltwater pool and large covered entertainment area complete with a TV—perfect for relaxing and enjoying a cocktail. The interior is colorfully curated to embody the essence of a vacation! Located just 5 minutes from the beach and 25 minutes to downtown. We have 16 Airbnb homes (family-owned and operated), and we're dedicated to finding the perfect fit for your getaway.

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.

5 out of 5 average rating, 185 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Apartment in St. Petersburg

A balcony area features a round wooden table surrounded by two chairs, one woven and one metal. A decorative piece is displayed on the wall, with two fishing poles leaning against the balcony railing overlooking the water and marina.

4.91 out of 5 average rating, 179 reviews

The Oasis

Welcome to Boca Ciega Oasis! The "Oasis" suite 409 has been totally remodeled in January 2022. This includes a new queen sofa couch in LR, new refrigerator, stove, washer/dryer, and balcony tables and chairs. The 4th-floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! Directly below the balcony is the swimming pool, Hot tub, and observation pier! The marina is to your left. See all while sitting in our bar height chairs and tables.

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.

An outdoor area features a putting green with blue flags, designed for practice, surrounded by artificial grass. Adjacent is a heated pool area, with clear water and a marked pool deck. A shaded section offers lounge furniture for relaxation.

4.9 out of 5 average rating, 125 reviews

3BR St. Pete Home, Heated Pool, 5 Min To Beaches

Looking for a beautiful pool home in St. Petersburg just 5 minutes from Florida's best beaches? This spacious 3BR, 2 bath home for 8 guests features a heated pool, ping pong table, dart board, putting green and pool basketball hoop. Enjoy fast WiFi, flat-screen TVs, and a fully equipped kitchen. The outdoor screened-in patio includes a comfortable sectional and smart TV, while the pool area boasts lounge chairs and furniture. Just 2 miles to the beach – perfect for relaxing.

4.97 out of 5 average rating, 257 reviews

An open-concept living area is displayed, featuring a cozy seating arrangement and a stylish electric fireplace. A modern kitchen with white cabinetry and granite countertops is visible in the background, alongside a dining area with a round table and upholstered chairs.

Condo in Seminole

UPDATEDVacation condo! HEATEDpool3 miles to beach

Wow!! Super value !! 2 bed 1 bath condo 1st floor - Welcome to Beachway Condos a GATED SAFE private full amenity community featuring a gym, tennis courts, HEATED POOL, grills, located 3 miles to the beautiful gulf beaches. You are close to everything - the Pinellas trail biking/walking is 1/4 mile away, Indian shores beach is the closest beach at 3 miles away. Clearwater/st Pete beaches are 7 miles away. Across the street are grocery stores malls, restaurants

4.87 out of 5 average rating, 166 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 )

Royal Orleans 203 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

4.93 out of 5 average rating, 114 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

Fantastic pool view Two Bed/Two Bath condo in gated community centrally located in southern Pinellas county. Enjoy the pool or just lounge around! 40 minutes to Tampa Airport, 20 minutes from downtown St. Petersburg, 10 minutes to the beaches. Fully equipped kitchen and washer/dryer inside the condo for your use. Third floor condo (stairs only) with vaulted ceilings and no one above you.

Popular amenities for Bay Pines rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

4.89 out of 5 average rating, 141 reviews

Hibernate in our Bear Creek Home

4.91 out of 5 average rating, 152 reviews

The living room features light-colored wood flooring and a neutral-toned sectional sofa positioned near a 65-inch Smart TV. A cozy chair and a decorative plant add warmth, while double doors lead to an outdoor seating area, enhanced by a vibrant green wall art piece.

Home in Largo

Luxe by the Bay - A Family Vacation Rental

4.95 out of 5 average rating, 146 reviews

A spacious living area features a large sectional sofa and a plush area rug, bathed in natural light from the windows. Two bedrooms are visible, adorned with comfortable bedding and accent pillows. A serene pool area is enclosed with a screen, providing a relaxing outdoor space.

Home in Seminole

Heated Pool luxury house, 4 mins from BEACH!

4.97 out of 5 average rating, 101 reviews

Private Pool & Short Drive to the Beach!

An inviting pool area is enclosed with a screen and features a unique shape. Clear water reflects the serene surroundings, while soft lighting hangs above. The patio is surrounded by a neat fence, ensuring privacy, and potted plants add a touch of greenery.

4.83 out of 5 average rating, 129 reviews

Beautiful & Exclusive house + Pool!

4.95 out of 5 average rating, 119 reviews

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.

Home in Largo

Palm Paradise - Family Amenities+Central Location

4.94 out of 5 average rating, 128 reviews

Home in Largo

Swim-Out Bedroom, Waterfall pool! The Peace Place

4.92 out of 5 average rating, 142 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

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

4.8 out of 5 average rating, 222 reviews

A cozy sleeping area includes a spacious bed dressed in white, adorned with colorful striped and patterned accents. A stylish sofa complements the room, while wooden cabinets provide storage. Wall art and decorative elements add visual interest to the neutral surroundings.

Condo in Redington Beach

Gulf view Condo with pool in Clearwater/St. Pete

4.83 out of 5 average rating, 250 reviews

A spacious living area is illuminated by natural light from large windows. Two sofas, one being a sleeper, are arranged around a circular glass table. The kitchen area features wooden cabinetry with a black countertop, while decorative wall frames provide a subtle touch.

Condo in St. Pete Beach

Amazing condo minutes to the beach*** heated pool

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.

Condo in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

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.

Condo in Largo

Boho Beach Condo

4.94 out of 5 average rating, 117 reviews

A spacious bedroom is equipped with a king-size bed, complemented by nightstands with lamps. A flat-screen smart TV is mounted on the wall. Artwork adorns the walls, and natural light filters through the windows, offering a view of the pool area from the ground floor.

Condo in Clearwater

By the POOL, Ground floor, King bed, NO PETS

4.85 out of 5 average rating, 116 reviews

A bright and airy living area features a spacious blue sofa and two cozy armchairs, inviting relaxation. A coffee table rests at the center, while a flat-screen TV is mounted on the wall. The open kitchen can be seen in the background, complete with modern appliances and ample counter space.

Condo in Treasure Island

Easy Breezy Intracoastal Manatees & Sunset Views

4.95 out of 5 average rating, 145 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

Other holiday rentals with a pool

A heated pool is surrounded by palm trees and lounge chairs, with a view of the sunset reflecting on the water. The area features a brick paved deck, creating a welcoming space for relaxation by the water.

4.75 out of 5 average rating, 63 reviews

Beautiful Sunset and Bay Views

Apartment in St. Petersburg

An expansive view of the bay is captured from the private balcony, featuring a glass table and two wicker chairs. The water reflects the clear blue sky, and nearby palm trees gently sway in the breeze, creating a serene setting for relaxation.

4.97 out of 5 average rating, 29 reviews

Bayview Balcony Condo, Hot Tub, Heated Pool, Bar!

4.98 out of 5 average rating, 54 reviews

A sparkling heated salt-water pool is surrounded by lounge chairs and palm trees, creating a relaxing atmosphere. The area features a safety fence, and the clubhouse is visible in the background, enhancing the community's inviting design.

Condo in Seminole

Minutes from the Beautiful Sandy Beaches!

4.92 out of 5 average rating, 36 reviews

An inviting outdoor gathering area is showcased, featuring a colorful bench adorned with vibrant murals. A fire pit is centered on a bed of pebbles, surrounded by plush seating. The backdrop is enhanced by string lights, casting a warm glow against the evening sky.

Home in Seminole

Casa Brisa - Htd. Pool-Unique Bungalows-Hot Tub

Aerial view of a three-story condominium building surrounded by lush greenery and water. The pool area is visible, featuring lounge chairs and a curved water design. The expansive outdoor space shows palm trees and walkways leading to the waterfront.

4.97 out of 5 average rating, 69 reviews

Penthouse condo w heated pool, beautiful view

A spacious outdoor area features a heated pool and a separate hot tub, both illuminated in soft blue light. A covered terrace provides shade, with comfortable seating options visible in the background. The landscape is accentuated by subtle stone textures and professional lighting.

4.93 out of 5 average rating, 89 reviews

Villa Kailāsa-Pool, 6 min drive to the Beach!

A wide view of Boca Ciega Bay is presented, showcasing calm waters under a partly cloudy sky. Lush palm trees frame the foreground, while boats can be seen in the distance, contributing to the serene waterfront atmosphere.

4.9 out of 5 average rating, 62 reviews

Gulf Waterfront Studio! Near Madeira Beach