Family-friendly holiday rentals in Lakewood Ranch

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

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

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Suncoast Villa - Relaxing getaway w private pool

Relax with the whole family at this peaceful place to stay. Suncoast Villa offers a bright, spacious retreat with open living areas, a fully equipped kitchen, and comfortable bedrooms designed for relaxation. Enjoy a private backyard oasis, perfect for unwinding after beach days. Ideally located near Gulf beaches, dining, parks, and golf—this inviting home is the perfect blend of comfort, convenience, and Florida sunshine. We are pet friendly (pet fee applies) and sits on over half acre lot.

Pool house(pets ok) Sarasota beaches, UTC mall.

Welcome to Coastal Manor, a refined coastal retreat in Bradenton, FL. This elegant 3BR, 2.5BA home offers a serene escape with a private heated pool, spacious fenced yard, and pet-friendly amenities. Located in Lakewood Ranch just minutes from UTC, Nathan Benderson Park, Premier Sports, IMG Academy and Gulf Coast beaches. It’s the perfect blend of charm and convenience. Designed with a muted coastal cottage vibe, this getaway invites you to relax, unwind, and explore the best of Florida.

House with heated pool, hot tub, golf course

Escape to paradise in this stunning Sarasota-Bradenton (sarasotaspahouse) Spa House! Located in a serene golf course community, this luxurious retreat features a heated pool, hot tub, and outdoor kitchen, perfect for relaxing under the Florida sun. Enjoy modern interiors, a fully equipped kitchen, and spacious living areas. Just minutes from beaches, dining, and entertainment, it's the ideal getaway for families or groups. Book your stay today and indulge in comfort and relaxation!

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

Private Heated Pool | Bradenton Vacation Home

Welcome to your private Bradenton pool oasis! . This heated pool house is well situated and well-maintained in a cul-de-sac and is central to the beach (15 minute drive to Anna Maria Island), IMG Academy, The Bradenton Country Club, famous Riverwalk, downtown and numerous restaurants and shopping options. Enjoy your own private oasis with plenty of space for your family and friends with 3 bedrooms that can sleep 8 guests and a fourth bonus room that can sleep 2 additional guests

Charming Country Cottage (Near Lakewood Ranch)

Named one of "Sarasota Area's Favorite Airbnbs" by Sarasota Magazine September 2021! Enjoy solitude in a country setting but have access to many activities, restaurants, and amenities only 10 minutes away in Lakewood Ranch community. The Guesthouse is a 40 minute drive to several wonderful beaches, including beautiful Siesta Key. Other nearby places of interests include UTC Shopping District, Hunsader Farms, TreeUmph and Ellenton Outlet Mall, Myakka State Park, and Celery Fields.

Luxury Pool Retreat Near Beach & Downtown 3BR/2BA

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into a luxurious experience the minute you arrive. Located on a lush quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

18th Green Getaway in Lakewood National Golf Club

** In High season, home must be booked ONLY ON FULL CONSECUTIVE CALENDAR MONTH(S), 3 MONTHS MINIMUM * Turnkey Executive Luxury home 3 bed/2.5 bath - 2 minutes’ from Clubhouse - 2 golf courses HIGH SEASON = DEC–APR: $11,000/m LOW SEASON = MAY–NOV: $6,500/m ** You may pay $642 membership transfer to use ALL the amenities: clubhouse, fitness center, tennis, pools, restaurants, spa, pickleball, 2 golf courses. If you don't transfer it you can't use ANY of the amenities. **

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.