Holiday rentals with a pool in Bayshore Gardens

4.96 out of 5 average rating, 104 reviews

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

Cottage in Palmetto

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

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, 115 reviews

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

Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

The outdoor space features a screened-in saltwater pool, surrounded by comfortable lounge chairs and a dining area. Ambient patio lights are strung overhead, and a large umbrella provides shade for the table accommodating six. Lush greenery is visible in the background, ensuring privacy.

4.85 out of 5 average rating, 107 reviews

LUXE! Heated Salt POOL! Close to Town, Beach, IMG

Beautifully updated coastal farmhouse home in a quiet cul de sac with a private pool oasis in the back. The salt water pool is completely screened in so you can stay in the pool all day and night long without worrying about flies or mosquitos. Kitchen is fully stocked and ready for you to cook up a storm! Or if you prefer, downtown Sarasota is only a short 15 minute drive away with plenty of eating options. Siesta key beach is rated the number one beach in the USA and it’s only 30 minutes away!

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 110 reviews

Pool house by the bay

Come stay in our beautiful, Mid-Century Modern, light drenched home just one block from the bay with a private pool. The private yard is surrounded by lush landscaping & the pool is the perfect place to cool off on hot afternoons. The house is spacious & minimally decorated with finds from our world travels. We've recently replaced the bed and the neighborhood is quiet and easy to explore on foot. Note: this is our home, so please expect a warm lived in feel in the space, not that of a hotel.

4.99 out of 5 average rating, 238 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 Sarasota

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

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 126 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

4.89 out of 5 average rating, 228 reviews

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guesthouse in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

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, 219 reviews

Backyard Oasis Heated Pool W/Tiki Bar Close To IMG

This gorgeous home has been completely renovated with an OPEN Concept layout, Brand 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 and Lido Beach, 10 minutes from SRQ airport and 10 min to both downtown Bradenton and Sarasota. HIGH Speed WiFi! Off Street Parking! Very Comfortable Foam Mattress Beds and Pillows! NFL Ticket Package On YouTube TV.

4.97 out of 5 average rating, 121 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.

A cozy lanai features a view of the tranquil lake, with vibrant turquoise chairs arranged around a patterned rug. Potted plants add greenery, while large glass doors provide natural light and an outdoor connection.

4.96 out of 5 average rating, 182 reviews

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor.

A spacious living and dining area features a table set for four with light-colored chairs. A comfortable sofa is arranged against the wall, and large sliding glass doors allow natural light to flood the space, providing views of the nearby lake and greenery.

4.98 out of 5 average rating, 203 reviews

Shorewalk full condo AnnaMaria Beaches IMG

1174 sqft Shorewalk condo with 2-bedroom, 2 bath , kitchen and living room unit on desirable ground level with a beautiful lake view Within very short walking distance to grocery ,movies, shopping and dining, This condo is about 9 miles from Sarasota airport and about 13 miles from downtown Sarasota, about 6.8miles from the Bradenton Beach , about 10 miles from Anna Maria Island Less than 1 mile to the big gate of the IMG academy

4.97 out of 5 average rating, 115 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

Bring the whole family to this great place with lots of room for fun. A spacious 2 bedroom, 2 bathroom condo on the second floor, newly renovated and fully equipped, is within walking distance of supermarkets, restaurants, the cinema, and bowling. Whether you are a single family on vacation, a couple enjoying a weekend getaway, or a sports team in training, we have you covered. Stay with us and enjoy all the comforts of home!

Popular amenities for Bayshore Gardens rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor area features two lounge chairs beside a small table, surrounded by lush palm trees. The clear water of the canal reflects the blue sky, while a screened enclosure contains a swimming pool nearby, creating a tranquil setting for relaxation.

5 out of 5 average rating, 25 reviews

Water's Edge: Charming Canal Oasis

An outdoor space features a heated pool surrounded by gray paving stones. A black pergola with string lights provides shade over a swing couch positioned next to a fire feature. Lounge chairs are arranged nearby, with a small table holding drinks. Lush greenery is visible in the backdrop.

4.93 out of 5 average rating, 171 reviews

Chic Oasis-Backyard Goals-Game Room-Pup Haven-Pool

A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.

4.97 out of 5 average rating, 103 reviews

Orange Oasis: Clean, heated pool, near beaches.

A single-story home is depicted, featuring a light-colored facade and a two-car garage. Lush green grass surrounds the property, with palm trees partially framing the view. The sky is filled with fluffy clouds, enhancing the welcoming appearance of the residence.

4.86 out of 5 average rating, 171 reviews

The Sea is Calling

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

4.97 out of 5 average rating, 104 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

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, 104 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Two brightly colored lounge chairs are positioned beside a pool, inviting relaxation. The pool is surrounded by lush greenery, providing a serene backdrop. A small table with a circular design sits between the chairs, complementing the tropical atmosphere created by an umbrella nearby.

4.9 out of 5 average rating, 78 reviews

CANAL FRONT! Bring or rent a boat, near AMI/IMG +

A cozy living room space features two blue armchairs and a matching sofa, arranged around a clear glass coffee table on a beige area rug. A large TV mounted on the wall displays a serene island scene, with sliding glass doors leading to an outdoor area.

4.95 out of 5 average rating, 111 reviews

Luxury Family Home w/ Heated Pool Near Siesta Key

Condo rentals with a pool

4.79 out of 5 average rating, 242 reviews

A spacious courtyard is highlighted by a heated pool surrounded by palm trees and lounge chairs. Lush green landscaping encircles the pool area, providing a tranquil setting. The exterior of the condominium features large windows, allowing for bright natural light.

Condo in Longboat Key

SRQ/Longboat Key Beach - kid friendly/romantic B1

An open kitchen features a dark granite countertop with seating for two. A set of pendant lights hangs above, illuminating the space. Modern appliances and warm wood cabinetry create a functional cooking area. A welcoming sign is displayed on the wall near the laundry machines.

4.85 out of 5 average rating, 134 reviews

Shorewalk upgraded condo upstairs unit 4415

4.89 out of 5 average rating, 155 reviews

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

Condo in Sarasota

6 min to Siesta Beach | Heated Pool | Lake View

4.88 out of 5 average rating, 118 reviews

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

4.91 out of 5 average rating, 191 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

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, 138 reviews

Cozy 2 bed/2.5 bath townhome

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

4.91 out of 5 average rating, 135 reviews

New Luxury 3/3 Condo in Margaritaville Resort

4.92 out of 5 average rating, 116 reviews

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

Condo in Siesta Key

Siesta Key Beach Front Condo

Other holiday rentals with a pool

A spacious living area features a light-colored sofa with patterned cushions, complemented by a wooden coffee table. A ceiling fan hangs overhead, while natural light illuminates the room through an adjacent doorway. A dining area is visible in the background, enhancing the open layout.

4.94 out of 5 average rating, 54 reviews

Shorewalk “A Little Piece of Paradise”

A well-appointed outdoor area features an expansive heated pool with a vibrant blue hue, surrounded by stylish loungers and an outdoor dining space. Soft lighting highlights the sleek architecture of the home in the background, with lush greenery enhancing the atmosphere.

4.91 out of 5 average rating, 11 reviews

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn

5 out of 5 average rating, 29 reviews

The mobile home features a covered porch with white railings, creating a welcoming entrance. Lush palm trees line the pathway, while the exterior showcases a light gray siding, under a partly cloudy sky. A concrete driveway leads up to the home.

Home in Ellenton

The Ellenton Retreat

5 out of 5 average rating, 34 reviews

A front porch is seen with a ceiling fan overhead and a partially covered entry door. A dining set is placed on the porch, complementing the home's inviting exterior with light-colored siding and white railings.

Home in Ellenton

The Ellenton Getaway

A spa with ambient lighting is positioned on a covered patio, overlooking a relaxed outdoor seating area. A grill is situated nearby, surrounded by a spacious deck that offers ample room for gatherings. Trees are subtly visible in the background, creating a peaceful environment.

4.96 out of 5 average rating, 69 reviews

A case of paradise

5 out of 5 average rating, 46 reviews

Seashells & Sunshine – Pool, Games, AMI Beaches

4.95 out of 5 average rating, 75 reviews

The exterior of a modular home is showcased, featuring a covered porch with two chairs under a sloped roof. Lush plants and palm trees surround the entrance, and a paved driveway leads to the home. Clear blue skies provide a bright backdrop.

Cottage in Bradenton

Cheerful 2 bedroom , plus bunk room vacation home.

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.