Holiday rentals with a pool in Bay Pines

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.

4.96 out of 5 average rating, 273 reviews

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

This unit is completely updated and modern! Enjoy a GORGEOUS view from the 20' private balcony overlooking the Bay, pool and hot tub! Watch dolphins every morning while sipping your coffee, or while enjoying a glass of wine in the evening! A 6-minute drive to Madeira Beach, and close to all amenities with many restaurants nearby, including Doc Ford's next door, and shopping within 7 minutes. Lots to do; close to fishing including deep sea, and jet skiing. 1 bedroom, sleeps 4; comfy pull-out.

4.95 out of 5 average rating, 133 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 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, 168 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 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, 408 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.

4.99 out of 5 average rating, 193 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.

4.91 out of 5 average rating, 181 reviews

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.

Flat in St. Petersburg

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, 280 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, 131 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.

A serene waterfront view is offered from the balcony, featuring a round table with two chairs. Palm trees frame the view, while calm waters reflect the clear sky, creating a peaceful outdoor space perfect for relaxation.

4.82 out of 5 average rating, 212 reviews

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

Apartment in Madeira Beach

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

4.99 out of 5 average rating, 218 reviews

Lux Condo w/ 2 balconies, Ocean & Marina views

This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

4.94 out of 5 average rating, 118 reviews

Flat in St. Petersburg

Snowbird paradise! Waterfront, pool, hottub

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, 247 reviews

Apartment 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

Popular amenities for Bay Pines rentals with a pool

Kitchen

Wifi

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.

4.88 out of 5 average rating, 148 reviews

Hibernate in our Bear Creek Home

4.97 out of 5 average rating, 153 reviews

Home in Pinellas Park

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Superhost

A private outdoor pool is surrounded by a spacious patio, featuring tropical landscaping and palm trees. The pool area includes a shallow ledge for lounging. The exterior of the home, with light-colored stucco, is visible in the background alongside a securely fenced yard.

Home in Largo

4.86 out of 5 average rating, 174 reviews

The Paradise Cove No. 1

4.91 out of 5 average rating, 116 reviews

An inviting outdoor space features a heated saltwater pool framed by paved stones. Two lounge chairs are positioned nearby on a grassy area, alongside a modern seating arrangement. Lush green plants in white planters enhance the environment, and wooden fencing provides privacy.

Home in Clearwater

Pet-friendly Beach Home with Heated Pool & Spa

Superhost

4.86 out of 5 average rating, 162 reviews

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

A vibrant game room features a foosball table and a ping pong table, illuminated by colorful lights. A blue sofa with accent pillows and a neon sign add to the playful atmosphere. Wall-mounted games and a fan complete the lively space for entertainment.

4.93 out of 5 average rating, 101 reviews

Modern Executive Home - Game Room - Htd. Pool

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.

4.95 out of 5 average rating, 106 reviews

Splash House - Relaxation Haven/Private Pool

A spacious backyard is highlighted by a solar heated pool, surrounded by lush greenery and native plants. Comfortable lounge chairs face the water, with colorful floatation devices resting nearby. A shaded area is provided by a patterned umbrella, offering a spot to relax and enjoy the scenery.

4.98 out of 5 average rating, 111 reviews

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath

Apartment rentals with a pool

Apartment in Redington Beach

4.85 out of 5 average rating, 639 reviews

Florida Island Beauty@theBeach@Heated Pool

Apartment in Madeira Beach

4.95 out of 5 average rating, 150 reviews

COASTAL CHIC! Luxury Apartment with Oceanviews

Apartment in Madeira Beach

A spacious open-concept living area includes a sleek kitchen with modern appliances and ample counter space. A dining table with six chairs and a pool table provide options for entertainment. Bright overhead lights create a welcoming atmosphere, with light-colored cabinets complementing the room.

4.94 out of 5 average rating, 101 reviews

Penthouse,intercoastal, 3/3 views/heated pool

Apartment in Treasure Island

4.93 out of 5 average rating, 154 reviews

Waterfront Condo - Dolphin sightings-Walk to beach

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.

Apartment in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

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

4.96 out of 5 average rating, 134 reviews

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.

Apartment in Clearwater

Bright and Spacious 1Bed/1Bath condo.

Apartment in Redington Beach

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.

4.8 out of 5 average rating, 249 reviews

Beautiful Studio on the paradise white sand beach!

Other holiday rentals with a pool

Apartment in Isla del Sol

5 out of 5 average rating, 10 reviews

Brand New condo with water views, Pool/Beaches

A modern kitchen features white cabinetry and a teal tiled backsplash. Three bar stools are arranged at the island, with stainless steel appliances visible. A cozy armchair with a leaf pattern is positioned in the living area, while natural light illuminates the space.

4.95 out of 5 average rating, 19 reviews

NEW Private Pool Close to Madeira Beach Golf Cart

The image showcases various areas of Surf INN. A bright bedroom features a large bed with colorful artwork above, while an outdoor space includes a cozy fire pit surrounded by teal chairs. A stock tank pool is visible, complemented by a colorful umbrella.

4.96 out of 5 average rating, 56 reviews

Tropical Garden | Fire Pit | Stock Tank Pool

A collage of images showcases the home’s features, including a spacious living room with a large TV, cozy bedrooms with colorful decor, and a refreshing pool surrounded by lounge chairs. Outdoor dining spaces, a BBQ grill, and vibrant landscaping enhance the inviting atmosphere.

4.93 out of 5 average rating, 42 reviews

Oasis St. Pete, Pool, Close to Beach/Downtown

Houseboat in Madeira Beach

A cozy living area features a gray sectional sofa adorned with cushions, complemented by a round wooden coffee table. Light filters through multiple windows, highlighting the soft blue and neutrals in the decor. A ceiling fan is overhead, and a potted plant adds a touch of greenery.

4.94 out of 5 average rating, 115 reviews

40ft Floating Bungalow with Resort Perks

5 out of 5 average rating, 15 reviews

The Walters

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.

4.91 out of 5 average rating, 64 reviews

Gulf Waterfront Studio! Near Madeira Beach

The image captures a view of the serene waterfront, featuring palm trees and lush greenery. A large swimming pool and a hot tub are visible in the foreground, surrounded by lounge chairs. The calm water reflects the clear sky, illustrating a tranquil outdoor setting.