Holiday rentals with a pool in Pinecraft, Sarasota Springs

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Top-rated rentals with a pool in Pinecraft, Sarasota Springs

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Guest favourite

Bungalow in Sarasota

4.91 out of 5 average rating, 354 reviews

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.

Guest favourite

Home in Sarasota

4.9 out of 5 average rating, 110 reviews

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

Guest favourite

Home in Bellevue Terrace

4.98 out of 5 average rating, 163 reviews

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

Guest favourite

Home in Bellevue Terrace

5 out of 5 average rating, 18 reviews

Sarasota Pool Home~at Legacy Trail/near Downtown

Welcome to this completely renovated pool home with private fenced-in pool area & plenty of outdoor seating! With bikes on-site, you can bike on the Legacy Trail bike path to downtown Sarasota or through Sarasota to Venice. Offering a fully equipped kitchen, tile, all new bedding, high speed wifi and TVs in each room. Enjoy local breweries, nearby parks, amazing restaurants, art, museums, and family-friendly attractions. This beachy Sarasota retreat will make your Florida stay unforgettable!

Superhost

Home in Sarasota

5 out of 5 average rating, 4 reviews

Legacy's Palm of Paradise | Pool+ Putt Putt Course

BNB Breeze Presents: Legacy's Palm of Paradise! Located just a short drive from Sarasota's beautiful beaches and a variety of attractions, Legacy's Palm of Paradise is the perfect base for exploring all that this city has to offer. Whether you're looking to soak up the sun or enjoy local dining, you'll find it all within reach. - Backyard Putt-Putt Course - Electric Bikes (available for extra purchase) - Private Heated Pool - Legacy Trail access - Covered Patio - Fire pit - Outdoor Kitchen

Top guest favourite

Home in Sarasota

5 out of 5 average rating, 71 reviews

Salt Water Pool on Golf Course

WELCOME TO OUR RETREAT! YOU'LL LOVE OUR OPEN-CONCEPT HOME. THE LR HAS A SINKING SOFA & CHAIR, TV WITH SOUND BAR, A DEDICATED WORK TABLE. THE NEW KITCHEN IS IDEAL FOR SOCIALIZING AND COOKING. GET COZY IN THE FR WITH THE COMFY SOFA BED SECTIONAL, FIREPLACE, AND ANOTHER SMART TV. WHEN IT IS TIME TO SETTLE IN, YOU WILL LOVE THE MBR AND MBA WITH THE 9 FT SHOWER WITH MULTIPLE SHOWER HEADS. POOL IS SO INVITING!! **ONLY 1 GROUP/STAY ALLOWED PER MONTH, HOST CALENDAR TO BE UPDATED AFTER BOOKING**

Top guest favourite

Home in Sarasota

5 out of 5 average rating, 24 reviews

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.

Guest favourite

Cottage in Bellevue Terrace

4.94 out of 5 average rating, 127 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

Guest favourite

Home in Arlington Park

4.96 out of 5 average rating, 125 reviews

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.

Superhost

Home in Bellevue Terrace

4.93 out of 5 average rating, 148 reviews

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.

Top guest favourite

Home in Sarasota

5 out of 5 average rating, 26 reviews

Belle of Sarasota

Bring the whole family to this great place with lots of room for fun. The home has everything you need for a fun vacation. Our pool is a saltwater pool and heated in the winter months for your convenience with a great lounge area leading out to the pool. There is also outside seating. We are 10 Minutes to downtown Sarasota. Beaches: - Siesta Key Beach, 8.9 miles - Lido Key/St Armand’s Circle, 7.5 miles

Guest favourite

Home in Sarasota

4.91 out of 5 average rating, 161 reviews

Charming Sarasota Home with Pool!

Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.