Vacation rentals with a pool in Bay Pines

4.95 out of 5 average rating, 129 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!!

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 225 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

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, 266 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, 405 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, 188 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, 180 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.

Apartment in St. Petersburg

4.94 out of 5 average rating, 114 reviews

Private balcony & heated pool hottub condo

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

4.98 out of 5 average rating, 243 reviews

An open living area features a modern kitchen with white cabinetry and a large island with bar seating. A comfortable couch is positioned in front of an electric fireplace, accompanied by a coffee table displaying books and a decorative plant. A wall-mounted TV displays a vibrant underwater scene.

Condo in Seminole

SHEEK and Glam- heated pool Updated! 3 mi to beach

UPDATED modern Light and bright colorful condo w HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/rest

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 )

Royal Orleans 208 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.

Popular amenities for Bay Pines rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.

4.99 out of 5 average rating, 140 reviews

Tootsie’s Beachside Retreat

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

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.

4.95 out of 5 average rating, 148 reviews

Heated Pool luxury house, 4 mins from BEACH!

A serene backyard features a rectangular pool surrounded by a spacious patio, dotted with palm trees. Two lounge chairs are positioned near the pool, complemented by a colorful umbrella. A screened-in lanai is visible in the background, enhancing outdoor relaxation.

4.97 out of 5 average rating, 101 reviews

Private Pool & Short Drive to the Beach!

4.91 out of 5 average rating, 101 reviews

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.

Home in Largo

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

Superhost

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

4.92 out of 5 average rating, 146 reviews

Clearwater Gameroom- Pool/Mini golf/Home Theatre

The exterior of the single-family home showcases a well-maintained facade, complemented by lush tropical landscaping. A spacious driveway leads to a garage, while a private, fenced yard is visible beyond. Large windows allow natural light to brighten the interior, set against a clear blue sky.

4.88 out of 5 average rating, 114 reviews

Tropical Pool Resort– Close to Beach, Lake, Golf

4.97 out of 5 average rating, 152 reviews

Clearwater LUXE! Tropical Family Beach Villa

Condo rentals with a pool

4.97 out of 5 average rating, 133 reviews

Condo in Clearwater

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

4.95 out of 5 average rating, 149 reviews

Condo in Madeira Beach

COASTAL CHIC! Luxury Apartment with Oceanviews

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

4.99 out of 5 average rating, 143 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.

Condo in Clearwater

Seasalt Breeze, by the pool, NO PETS

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.

Condo in Largo

Boho Beach Condo

4.8 out of 5 average rating, 249 reviews

An outdoor swimming pool is surrounded by a well-maintained paved area and vibrant landscaping. Palm trees provide shade near the pool, while the adjacent building features two levels with balconies overlooking the area. The inviting water reflects sunlight under a clear blue sky.

Condo in Redington Beach

Beautiful Studio on the paradise white sand beach!

4.84 out of 5 average rating, 172 reviews

A bright and airy living area features a comfortable couch facing a modern television. A coffee table sits in the center, with a view of the intracoastal waterways visible through large sliding glass doors that lead to the balcony.

Condo in Madeira Beach

Lovely Water View Condo, Top Floor, Steps to Beach

4.95 out of 5 average rating, 147 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

Other vacation rentals with a pool

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!

The image showcases a pool area overlooking a serene waterway, bordered by palm trees. Sunbeds are positioned around the pool, and lush greenery is visible in the foreground. A tranquil sky with scattered clouds enhances the view of the water, creating a peaceful atmosphere.

4.97 out of 5 average rating, 32 reviews

BOCA CIEGA Condominium - 107

4.98 out of 5 average rating, 57 reviews

5 Min to Beach: FREE Heated Salt Pool - Hot Tub

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, 90 reviews

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

5 out of 5 average rating, 9 reviews

A serene view of a saltwater infinity pool is captured, bordered by a patio featuring lounge chairs and a shaded table. Lush palm trees surround the area, enhancing the tranquil atmosphere. Beyond the pool, the expansive water of Boca Ciega Bay stretches into the distance under a clear blue sky.

Home in Jungle Terrace

Mid Mod Waterfront Home with Pool + Hot Tub

A spacious living area opens up to a private balcony, offering expansive water views. Sliding glass doors provide a seamless transition to the outdoor space, where high-top chairs are positioned for leisurely observation of the surrounding scenery.

4.97 out of 5 average rating, 71 reviews

Penthouse bayfront condo w heated pool/waterview

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