Holiday rentals with a pool in Fruitville

Serenity at Whispering Oaks/Heated Pool

25-VR-000040 Escape to Sarasota in this spacious 3BR/2BA home with a private pool, tucked away on a quiet street. Just minutes from Siesta Key Beach, downtown, and local attractions – it's the perfect spot! Located on a quiet street, yet just minutes from Sarasota’s best attractions: - Siesta Key Beach – 10 miles - Lido Key Beach - 7 miles - Downtown Sarasota dining & arts – 10 minutes - St.Armands Circle shopping & restaurants –7.5 minutes - Parks, golf, and family-friendly activities nearby

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.

Sunshine House, near Downtown, Legacy Trail, Beach

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.

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

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.

The Oasis

Welcome to The Oasis, your Florida home away from home! Centrally located, between siesta key and st Armand’s circle, near many fantastic restaurants, grocery stores, and downtown. This home has everything you need for a fantastic stress free stay in Sarasota. A luxurious Italian style pool and garden area, a spacious indoor area with a full sized kitchen, king bed, queen bed, 1 twin bed and 2 twin air mattress. 4 smart tvs. We love this stunning and cozy home and we’re sure you will too!

Sunny Palm Villa

Welcome to Sunny Palm Villa! This family friendly 3 bedroom 2 bathroom home with a heated pool is just the place you have been looking for. A wonderful place to unwind and relax by the pool or one of the nearby beaches. Conveniently located 20 minutes from Siesta Key Beach or Lido Key Beach. Only 15 minutes from University Town Center shopping, Mote Aquarium and Nathan Bendersen Rowing Park. The Legacy Bike Trail and famous Dutch, Amish restaurants in Pinecraft only 5 minutes away.

Family Friendly w/Free Heated Pool Near Beach

Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀  Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

GARDEN VIEW HOUSE WITH A POOL

Relax with the whole family at this peaceful place to stay. Private Garden Front Home. Located 7 miles to the Siesta Key, #1 beach in United States. 1 mile to Legacy Trail. Trail is 18.5 mile Connecting Sarasota and Venice, Florida. This 3 bedrooms 2 bath home offers everything you need for your next vacation getaway! The kitchen is equipped with everything needed to make your favorite home-cooked meals and host the family at the table or on the covered outdoor screened-in lanai!

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

Sunshine House- Sarasota Pool Retreat

Welcome to the Sunshine House a sunny Sarasota retreat! This charming 3-bedroom, 2-bathroom home features a salt water heated pool and is just 20 minutes from the stunning Lido and Siesta Key Beaches. Perfect for families or groups, our home offers a spacious living area, fully equipped kitchen, comfortable bedrooms and an office setup. Relax by the pool, enjoy nearby dining and shopping, or explore the beautiful beaches. Your perfect getaway awaits!

Exclusive pool villa near Siesta Key 3BR/2BA

Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market—all just minutes away!