Holiday rentals with a pool in Sarasota

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Sunshine House, close to Downtown

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

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

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.

The Wisteria Oasis W/ heated pool & hot tub

Come Relax with your family at this peaceful 3 bedroom cottage, It has a private fenced in backyard w/ new heated saltwater pool, hot tub, hammock & swings,and a fire pit to make s’mores! Yes its stocked with beach gear and a short drive to the beautiful siesta key and lido key beaches. Also minutes from the Bayfront park where u can watch amazing sunsets and the downtown sarasota dining spots! Arlington park is in the neighborhood with trails- play area- pool- outdoor gym.

Lido Key/St. Armand's Studio apt 8

Short walk to Lido Beach. Studio apartment. This is a October 2024 remodel. and dining, family-friendly activities, and public transport all very close by. Great for kayaking and biking. Walking or biking distance to Lido Beach, St. Armand's Circle and Ted Sperling Kayak Park. This one room studio is good for a couple or solo adventurers. Short drive to downtown Sarasota and LBK. Ideal for budget and value conscious lodgers looking for short term stays.

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Luxury Heated Pool/ Family Oasis/Siesta Key3BR/2BA

Welcome to your private oasis! This stunning pool home has undergone a meticulous renovation, offering a spacious and luminous retreat. Nestled on a serene street, it provides a peaceful escape while being in close proximity to Sarasota's top destinations. Whether you're seeking the sun-kissed shores of Siesta Key Beach, the vibrant downtown scene, or the flavors of the Fresh Fish Waltz Market, this home offers easy access to it all.