Holiday rentals with a pool in Pinecraft, Sarasota Springs

5 out of 5 average rating, 102 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

4.91 out of 5 average rating, 352 reviews

Bungalow 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.

4.98 out of 5 average rating, 162 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

5 out of 5 average rating, 9 reviews

Private Poolside Paradise | Walk to Legacy TRL |

BRAND NEW heated Saltwater Pool! Fresh remodel, all new furniture ; a stylish experience Centrally located 6 minute drive to downtown! Walk to Legacy trail! Sleeps 7, Mid-Century Modern decor and private fully fenced yard. New furniture. Dining area & large breakfast bar, living room & hangout nook. 3 full size bathrooms!! Large European style kitchen; new stainless steel appliances and quartz countertops. 1 car garage and new laundry machines. Swing in the tree hammock, grill by the pool ☀️

5 out of 5 average rating, 23 reviews

Sarasota Paradise/Stunning Home/Heated Pool

Bring the whole family. This home has lots of things to make 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. Beaches: - Siesta Key Beach, 7.7 miles - Lido Key/St Armand’s Circle, 7.5 miles

Superhost

4.88 out of 5 average rating, 149 reviews

Cottage On Bay (private backyard, near beaches)

Welcome to our newly renovated, stunning mid-century modern 3-bedroom home. Explore the #1 top-rated Siesta Key Beach, just 7.9 miles away, and Lido Key Beach, a short 6.5 miles away. Discover downtown Sarasota and the fascinating Amish village of Pinecraft nearby. Indulge in ample amenities, plush bedding, and relax in the spacious backyard and screened-in lanai. Spend the day lounging by the heated, saltwater pool and experience a vacation like no other in this gorgeous rental property.

5 out of 5 average rating, 70 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**

4.94 out of 5 average rating, 127 reviews

Cottage in Sarasota

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.

4.94 out of 5 average rating, 152 reviews

La Hacienda / heated pool, hot tub, 6 mi to beach

Experience the allure of La Hacienda, a charming rental with a warm Southwestern-inspired interior with unique touches. This 4-bedroom, 2-bath home features a spacious living room with comfortable seating and multiple smart TVs. The private backyard awaits with a heated pool and hot tub for ultimate relaxation and entertainment. Located near downtown, you'll have easy access to beaches and dining. Indulge in the perfect blend of chillin', grillin' and sippin' at La Hacienda!

Superhost

4.92 out of 5 average rating, 107 reviews

The Palms (heated private pool, near Pinecraft)

Experience a vibrant, newly renovated two-story featuring a stunning heated saltwater pool. This immaculate 3-bedroom retreat offers versatile bedding, including king, queen, and full bunk beds, plus a futon for maximum comfort. Set on a tranquil street, you'll have seamless access to Siesta and Lido Beaches, the charming Pinecraft Amish Village, shopping, and Downtown Sarasota. Your dream vacation awaits at this sunlit getaway. Siesta Beach 7.8 mi, Lido Beach 6.2 mi.

4.93 out of 5 average rating, 87 reviews

Sarasota home featuring private salt water pool

Beautiful 3 bedroom, 2 bath home with newly refinished private pool with heating offered in a fenced in backyard. Just a 12 minute drive to the perfect Lido Key Beach and St. Armands Circle, walking distance to Payne Park and outer parks of downtown, a short 5 minute drive to the heart of Downtown Sarasota, this house is the ideal place for your next relaxing vacation or extended stay. Conveniently located close to Sarasota- Bradenton airport as well as Siesta Key!

Superhost