Holiday rentals with a pool in Pinecraft

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.

LUXE home 6mi to Siesta w/ incredible pool area!

Welcome to The Palmieri - the ideal Sarasota family vacation destination! Minutes from DT, Siesta & Lido beach, our beautifully styled home features an incredible backyard with a heated pool, hot tub, fire pit, playland, and a shaded lounge. Spacious and open inside, with a fully equipped kitchen, and all the cozy feels of home. The finished garage houses beach supplies for your convenience, and thoughtful touches throughout combine comfort & luxury for an unforgettable experience. VR24-00277

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL. NONTOXIC + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

Sarasota Paradise/Stunning Home/Heated Pool

Bring the whole family. This home has lots of things for a fun vacation. Make great memories as you entertain in the lg kitchen, grab some coffee at the bar, sit on the patio and enjoy the beautiful view. Enjoy a walk or bike ride on the nearby Legacy Trail. Let this be a place where you experience the Blessings of God and be refreshed by His Grace as you spend time in our home away from your home. No pets! Beaches: - Siesta Key Beach, 7.7 mi. - Lido Key/St Armand’s Circle, 7.5 mi.

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.

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool.

White Sands Villa - Heated Pool/Spa - Near Beaches

Retreat to a stunning 4-bedroom villa with a modern interior. The expansive backyard boasts a screened-in lanai, pool, hot tub, and children's swing set, ideal for family getaways. Enjoy comfort and convenience with thoughtful amenities, plush mattresses, and smart TVs in every bedroom. Just minutes away from Siesta Key (7.3 mi), Lido Beach (6.5 mi), downtown Sarasota (2.5 mi), and the charming Amish Village of Pinecraft. Your perfect vacation home awaits.

Heated Pool 3bdr 2bth Close to Downtown

Freshly remodeled home as of 2021, Great for family vacation. Amazing location right in the middle of town, no more than a ten minute drive to the incredible attractions. Easy drive to the #1 beach/Siesta beach world famous for its astonishing clear waters and impeccable views. This home has a private entrance with a heated outdoor pool. We are also pet friendly/dog. Small dog only, under 15 pounds, pet fee required.