Vacation rentals with a pool in Bayshore Gardens

An open living area is showcased, featuring a spacious sectional sofa and a coffee table. A large TV is mounted on the wall, with a stylish media console beneath. A dining table with chairs is visible, illuminated by natural light from the nearby windows.

4.96 out of 5 average rating, 26 reviews

The Lovely Family House

Your family will be close to everything when you stay at this centrally located place. Walk to IMG and SCF. Near beaches(Anna Maria,Holmes Beach,Coquina,and more). Screened in pool and patio. Plenty of places in the house to be together with others and have personal quite space too. Sleeps 11 comfortably. RV or trlr parking available. 4-5 car driveway. Grill, bikes, outdoor toys, beach gear, fooseball table, and more. 3 bedrm and 2 ba w/ sofa sleeper. Max 1 Dog. No cats. No indoor smoking

An outdoor space is highlighted by a blue illuminated pool, creating a calming atmosphere. A fire pit is positioned in the foreground, with flames flickering softly. The enclosed area offers a sense of privacy, enhanced by surrounding greenery.

4.94 out of 5 average rating, 102 reviews

Cozy Beach House Including King Size Suite !

Welcome to our beach home ! Located in a beautiful neighborhood where you can unwind & relax with the family after a long day at the beach. We are located only a short drive to the finest beaches in FL where you can find sand dollars with the kids & view breathtaking sunsets ! Play a game of pool, grill out on our patio, & enjoy our fire pit & enclosed pool !! This easy access one-level home sleeps up to 8 people. Conveniently located within minutes from groceries, restaurants, and attractions.

A modern bedroom features a four-poster bed dressed in neutral linens, complemented by wall-mounted lamps. A decorative bench is placed at the foot of the bed. Natural light fills the room through large sliding glass doors that open to a private balcony.

4.92 out of 5 average rating, 141 reviews

4BR Golf View-Heated Pool/IMG Academy/Near Beaches

Welcome to The Cortez Retreat! We are delighted to have you. This gorgeous home has been completely renovated in a peaceful neighborhood overlooking the IMG Golf Course. Pack your bags and get ready to escape to SW Bradenton, just 6 miles from SRQ Airport and 10 miles from downtown Sarasota. Siesta Key has been rated the #1 beach in the US, only 17 miles from the home. Additionally, Ana Maria Island is 11 miles, Lido Beach 12 miles, Coquina Beach 9 miles, and Longboat Key 12 miles from home!

Apartment in Indian Beach-Sapphire Shores

The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.

4.96 out of 5 average rating, 178 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

4.99 out of 5 average rating, 267 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Whitfield

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

5 out of 5 average rating, 7 reviews

Home in Sarasota

Sarasota Family Home | Private Heated Pool | Relax

🌴 Enjoy a private heated pool at this Sarasota–Bradenton area family home, The Getaway, thoughtfully set up as your true Home Away From Home. With open living spaces and flexible sleeping for up to 10 guests, it’s perfect for families or groups seeking comfort, privacy, and space to relax. Located in a quiet neighborhood, yet with easy access to beaches 🏖️, dining, and local attractions, this home is designed for real vacations—not just photos. Book now and make Florida your next getaway!

4.98 out of 5 average rating, 225 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Sun-Kissed Memories: Open Thursday, March 26th!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

A bright and welcoming master bedroom features a spacious bed with neutral bedding, flanked by two bedside tables. Natural light enters through sheer curtains, illuminating the dark wood accents in the room. A large full-length mirror is positioned nearby, adding depth to the space.

5 out of 5 average rating, 19 reviews

Garden Home/Heated Pool/King-Bed/20 min Beach/Pets

Nestled beneath towering trees, this cozy 3-bedroom, 2-bathroom home offers a peaceful getaway. The screened-in heated pool and patio provide a quiet spot to relax and enjoy nature’s beauty in privacy. With new beds and many thoughtful amenities, it’s a comfortable retreat for your stay. Whether you're swimming, grilling, or simply enjoying the surroundings, this home offers a calm atmosphere to unwind and share time with family or friends in complete comfort. Message us with questions.

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5 out of 5 average rating, 111 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

4.96 out of 5 average rating, 129 reviews

A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.

Cottage in Bradenton

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

An aerial view captures the surrounding neighborhood by Sarasota Bay, featuring tree-lined streets and waterways. A mix of residential homes is visible, along with green parks and recreational areas, demonstrating the serene coastal environment a short distance from the water.

5 out of 5 average rating, 8 reviews

ON SALE - Canalfront, Pool, Grill, Dock

Gather your loved ones and prepare for an unforgettable Florida getaway at Bayshore Surprise! This exquisitely remodeled home epitomizes coastal Florida living, offering high-end finishes, top-tier amenities, and a serene environment to relax and unwind. Whether you're lounging by the pool, enjoying the built-in wet bar, or exploring the nearby Sarasota Bay, this ground-floor retreat has everything needed for the perfect vacation.

A spacious backyard is showcased with a freshly renovated salt-water pool at the center. Comfortable lounge chairs are positioned near the pool, with a tiki bar visible in the background. Lush greenery and a putting green enhance the inviting outdoor space.

4.84 out of 5 average rating, 241 reviews

Backyard Oasis, Heated Pool Tiki Bar Near IMG

This gorgeous home has been completely renovated with an OPEN Concept layout, New Heated (85 degrees) Salt Water Pool, Tiki Bar with 50" TV, Putting Green, Kornhole boards, and Gas Grill! Located 5 Minutes from IMG Academy and 15-20 Minutes from AMI & Lido Beach, 10 minutes from SRQ airport and 10 min to downtown Bradenton and Sarasota. HIGH Speed WiFi, Off Street Parking, very comfortable foam mattress beds and pillows.

Popular amenities for Bayshore Gardens rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 111 reviews

Home in South Bradenton

[Guest Favourite] Family Fun Oasis | Heated Pool,

5 out of 5 average rating, 5 reviews

Heated Pool Retreat Near IMG & Anna Maria Island

4.86 out of 5 average rating, 137 reviews

Home in Longboat Key

Summer House longboat key

An aerial view of a residential property surrounded by lush green lawns and mature trees. The home features a red roof and is complemented by a private pool in the backyard. Adjacent to the property, a golf course can be seen in the distance.

4.88 out of 5 average rating, 85 reviews

Luxurious summer home w pool | Mins to IMG Academy

4.96 out of 5 average rating, 24 reviews

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

A private screened pool area features a vibrant blue pool surrounded by loungers and colorful pool floats. A well-maintained lawn and mini-golf area are visible, while a game room with bright visual elements offers entertainment options. A cozy living space showcases a comfortable sofa and artistic wall design.

4.93 out of 5 average rating, 56 reviews

Heated Pool-Near Beaches-MiniGolf-Arcade

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 400 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

5 out of 5 average rating, 125 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

Condo rentals with a pool

A bright bedroom features a spacious bed with light bedding and a wicker nightstand on either side, each topped with a lamp. A chair rests in the corner, and a large window offers views of greenery outside, bringing in ample natural light.

4.83 out of 5 average rating, 104 reviews

Palms Villa: Cozy & Minutes from Anna Maria Island

4.92 out of 5 average rating, 114 reviews

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

Condo in Siesta Key

The Honeymoon Suite on Siesta Key Beach

4.98 out of 5 average rating, 100 reviews

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

Condo in Holmes Beach

A Coastal Retreat Steps From the Sea

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

4.97 out of 5 average rating, 198 reviews

Luxury 3/3 Margaritaville Resort

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 126 reviews

A&A's Paradise near IMG & Anna Maria beaches

4.88 out of 5 average rating, 127 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

The inviting living area features a brown leather sofa paired with a teal accent chair. A circular mirror is positioned above a coffee table, which holds magazines. A patterned rug sits beneath, and natural light filters through the sliding glass doors.

4.96 out of 5 average rating, 147 reviews

Cozy 2 bed/2.5 bath townhome

4.89 out of 5 average rating, 208 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Other vacation rentals with a pool

5 out of 5 average rating, 84 reviews

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

Home in Sarasota

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

4.96 out of 5 average rating, 28 reviews

100 yr Old Stone Home + Pool + 9 miles to beaches

4.9 out of 5 average rating, 40 reviews

A vibrant living area features a bright blue sofa with a patterned throw and a green coffee table. Large glass windows allow natural light to fill the space, while two oversized pink chairs add a playful touch. Lush greenery is visible outside.

Townhouse in Bradenton

Art and Design in Bradenton Villa

A living area features a blue sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, and a light-colored desk with a chair is positioned nearby. Two windows allow natural light to fill the space, complemented by tropical-themed artwork on the wall.

4.8 out of 5 average rating, 10 reviews

Coastal Retreat Cottage 1 b/1b

The screened patio features a tranquil saltwater pool, reflecting the vibrant colors of a sunset. Lush greenery surrounds the pool, offering views of the natural waterway below, where trees and wildlife can be observed.

5 out of 5 average rating, 34 reviews

Waterfront/Kayak with Manatees/Pool/Fish

5 out of 5 average rating, 45 reviews

Freshly Renovated Vacation Villa at Shorewalk

The exterior of the home is presented, featuring a single-story design with tropical landscaping. Palm trees and vibrant greenery are visible, alongside a well-maintained lawn. A paved driveway leads to a garage, with a covered porch inviting guests to enter.

4.94 out of 5 average rating, 34 reviews

Settle Down in Sarasota

A screened-in pool area features a sparkling pool accompanied by a spa, both bordered by smooth concrete. Surrounding the pool are lounge chairs in bright colors, with lush greenery visible through the fencing, offering a serene outdoor retreat.