Holiday rentals with a pool in Bay Pines

A serene swimming pool is bordered by palm trees, with lounge chairs positioned around the edge. The pool area is complemented by views of the water and lush greenery, creating a tranquil outdoor escape.

4.85 out of 5 average rating, 101 reviews

Sunny St. Pete Getaway with Dolphins

Escape to this stunning waterfront luxury condo, perfectly situated just minutes from beaches, shops, and restaurants. Enjoy spectacular Bay views from your private large balcony, or unwind by the heated pool and spa overlooking the water. ✨ Resort-Style Amenities – Heated pool, spa, fitness center & outdoor dining area withBBQs ✨ Comfort – queen platform bed & firm mattress, bathtub/shower, fully equipped kitchen, new washer/dryer combo in-unit ✨ Dining – Doc Ford’s Rum Bar & Grill next door.

4.94 out of 5 average rating, 142 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!!

4.98 out of 5 average rating, 169 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.

4.96 out of 5 average rating, 279 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 coffee, or while enjoying a glass of wine with the sunset! A 6-minute drive to Madeira Beach, close to all amenities, many restaurants nearby, incl. Doc Ford's next door, rated #1, shopping 7 mins. Lots to do; close to fishing including deep sea, jet skiing. 1 bedroom w/KING bed, comfy QUEEN pull-out; SLEEPS 4.

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, 416 reviews

Colorful Tropical POOL Oasis- 5 Minutes to Beach

Presented by St. Pete Vacation Homes, this vibrant, colorful 2BR/1BA home sleeps up to 8 guests and is perfect for smaller groups. Enjoy a wide open floor plan, saltwater pool, fire pit and a spacious outdoor dining & lounge area with an outdoor TV and fridge. Optional pool heat available. Located just 6 minutes to the beaches and 24 minutes to downtown, we have additional nearby homes available so check us out--we are always happy to help find the best option for your group situation.

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, 201 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.

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, 284 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.

4.89 out of 5 average rating, 137 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.

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, 117 reviews

Tropical Pool Resort– Close to Beach, Lake, Golf

Relax in this spacious 4BR pool home near Florida’s sandy beaches & Lake Seminole Park! Safe and Ready! Enjoy a private fenced yard and pool, tropical landscaping, and plenty of space for family, work, or play. Just minutes to golf, tennis, dining & top attractions. Perfect for vacations, snowbirds, or remote work with 2 desks, a stocked kitchen & fun extras like bikes, beach gear & fitness space. Ask about special promotions then book your tropical retreat today!

4.98 out of 5 average rating, 260 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 FREE 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/restaurants and the Pinellas trail !

A serene outdoor space features a heated saltwater pool surrounded by a screened enclosure. Lounge chairs are positioned poolside, and a children's swing set is visible in the background. The vibrant sunset creates a warm ambiance over the tranquil setting.

4.96 out of 5 average rating, 136 reviews

Sleeps 8 Near Beach | Pool + Game Retreat

Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

Apartment in St. Petersburg

4.95 out of 5 average rating, 128 reviews

Waterfront studio! Heated pool and 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!

Popular amenities for Bay Pines rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 12 reviews

Private Oasis/Heated pool/5 min. to Mad Beach

4.98 out of 5 average rating, 166 reviews

Home in Pinellas Park

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

*Newly Listed*The South Wing w/ Saltwater Pool

5 out of 5 average rating, 3 reviews

Home in Largo

Largo Pool Home with Grill & Private Yard

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.

4.94 out of 5 average rating, 96 reviews

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

Home in Indian Rocks Beach

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, 362 reviews

Stunning views! Spot dolphins from the pool!

4.95 out of 5 average rating, 114 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 Largo

Splash House - Relaxation Haven/Private Pool

Home in Redington Beach

Redington Beach near beach on ICW w/pool & dock

Condo rentals with a pool

4.83 out of 5 average rating, 102 reviews

An aerial view captures the coastline with soft, sandy beaches meeting vibrant turquoise waters. Nearby, a boat glides through the water, while the shoreline is lined with a mix of buildings and natural landscapes against the backdrop of a colorful sunset.

Condo in Madeira Beach

Lovely-2 bedroom condo with 2 pools, Madeira beach

4.83 out of 5 average rating, 145 reviews

Condo in Madeira Beach

Beachfront balcony view heated pool hot tub

4.92 out of 5 average rating, 119 reviews

A clear view of a turquoise pool is presented, surrounded by lounge chairs. Beyond the pool, the white sandy beach stretches out, dotted with blue umbrellas. The calm waters of the Gulf of Mexico can be seen in the background under a bright sky.

Condo in Madeira Beach

Beach Front Gulf View at John’s Pass Medeira Beach

4.93 out of 5 average rating, 120 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

4.99 out of 5 average rating, 214 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

4.98 out of 5 average rating, 153 reviews

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

Condo in Treasure Island

Beach, dolphin/manatee sightings, fishing, sunsets

4.98 out of 5 average rating, 162 reviews

Condo in Treasure Island

Guest Favorite | Beach • Pool • Intracoastal

An inviting balcony view overlooks a spacious pool area and the intercoastal waters, framed by palm trees. A light-filled living area features comfortable furnishings and a television, while the dining space and kitchen are visible, providing a warm atmosphere for relaxation and enjoyment.

4.86 out of 5 average rating, 322 reviews

Breathtaking Waterview & Pool View Condo

Other holiday rentals with a pool

An outdoor kitchen area features a bar with high-backed stools and a comfortable seating arrangement of sectional couches, providing ample space for relaxation. The space is decorated with greenery, and a partially visible pool adds a refreshing element to the setting.

4.92 out of 5 average rating, 65 reviews

Exclusive indoor pool house near the beach 3BD/2.5

5-Min to Beach • Pool • Beach Gear • Family House

Guesthouse in Crescent Lake

A serene outdoor space features a saltwater pool surrounded by lush greenery. Two lounge chairs are positioned under a striped umbrella, providing shade on the pool deck. The light-colored stone tiles enhance the calming atmosphere of this private retreat.

5 out of 5 average rating, 26 reviews

Luxury Pool House

Apartment in Madeira Beach

A spacious living area features a large sectional couch adorned with decorative pillows. Natural light floods the room through sliding glass doors that lead to a balcony, framed by modern art pieces depicting coastal scenes. A round wooden coffee table rests on a textured area rug.

5 out of 5 average rating, 22 reviews

The Harbor Condo Beach Escape!

4.75 out of 5 average rating, 69 reviews

Mad Beach Bungalow-Heated Pool, 4 Mins to Beach

Coastal Canopy | Pool, Hot Tub & Big Yard

The outdoor deck features cozy seating options, including a hanging chair and an outdoor dining setup beneath a gazebo. Soft lighting illuminates the area, which overlooks a calm pond surrounded by lush greenery, enhancing the tranquil ambiance of the retreat.

4.97 out of 5 average rating, 65 reviews

Heaven on the Water w/ Deck & BBQ | 5 min to Beach