Family-friendly vacation rentals in Whitfield

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Top-rated family-friendly rentals in Whitfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A screened saltwater pool area showcases a gentle glow from color-changing lights. Two lounge chairs are positioned nearby, along with an outdoor seating arrangement featuring cushions. Lush greenery surrounds the space, providing privacy and a tranquil atmosphere.

Home in Sarasota

4.95 out of 5 average rating, 103 reviews

Saltwater Pool + Huge Kitchen | Hammock | Open Con

Planning to stay a while? We love long getaways! Ask us about special discounts for stays of 14 nights or more — your extended vacation just got even sweeter! Discover a luxurious one-level retreat just steps from Sarasota Bay and a short drive to Lido Key, Longboat Key, Siesta Key, and Anna Maria Island! This beautifully appointed home offers elegance, comfort, and fun for your perfect vacation. Step inside and be wowed by the spacious **gourmet kitchen**, a chef’s dream featuring a double

Guest favorite

A screened lanai area features a glistening pool surrounded by a spacious deck. Two cushioned lounge chairs are positioned for relaxation. Lush palm trees frame the view, complementing the tranquil setting of the fenced backyard.

Home in Sarasota

4.89 out of 5 average rating, 132 reviews

Summer Vacay Time! Gameroom +Private Pool+King Bed

Escape to Paradise Palms, a tropical, well equipped home with lots of room for fun and relaxation. This spacious property boasts a great layout for groups including a large dining area with seating for 8 comfortably and a fully equipped kitchen.Step outside into the fully screened lanai area with a lounge area with a 60'' TV, dining table with seating for 6, fenced yard and a large pool with plenty of pool toys for your enjoyment. Close to Siesta+Lido beaches! 5 miles to IMG +14 miles to AMI!

Top guest favorite

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Sarasota

4.99 out of 5 average rating, 219 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Superhost

A charming old Florida home is shown with a light-colored exterior and blue shutters. A sizable tree stands in the front yard, providing shade. A gravel pathway leads to a covered carport on the right, surrounded by lush tropical vegetation.

Home in Sarasota

4.89 out of 5 average rating, 373 reviews

Beautiful and Restful Sarasota Florida Retreat

This old Florida home has been updated with granite counters in the kitchen with newer appliances, ceramic tile, and wood flooring. There is plenty of room to spread out in the main living room and within the wood wall and ceiling finished gathering room. The backyard patio area is perfect for outdoor BBQs. The lush tropical landscaping provides the old Florida home feel. The best amenity is a semi-private outdoor shower with lush vegetation screening. Perfect for the outdoor enthusiast.

Guest favorite

A cozy living area is highlighted by plush pillows in vibrant orange and white. In the background, the kitchen is partially visible, featuring a bottle of wine and glassware on a tray, with a coffee maker nearby.

Guest suite in Bradenton

4.91 out of 5 average rating, 197 reviews

Live and Enjoy Arlet’s Dream

Enjoy the simplicity of this quiet and central accommodation from which you can easily access exquisite restaurants, fast food place, airports, shopping malls, cultural and recreational centers as well as the beautiful beaches that characterize this city .Feel the warmth and enjoy the great sunset of Ana Maria Island and Coquina beach.Walk along the white and fine sand of a set of beaches that will be within your reach due to the central and privileged location of this accommodation.

Superhost

The covered swimming pool area features a spacious rectangular pool with crystal-clear water. Surrounding the pool are several lounge chairs, and the area is framed by a screened enclosure. Landscaped borders enhance the outdoor space with a touch of greenery.

Home in Sarasota

4.82 out of 5 average rating, 190 reviews

Pool | Game Room | Fire Pit | Pet Friendly | 3 TVs

Our spacious single-level house is perfect for families or groups as it comfortably sleeps 10 people. The home features a renovated deep saltwater pool, an outdoor seating area with a BBQ grill, three 4K smart TVs with local channels, a game room and a fire pit. The backyard is fenced and well-behaved dogs are welcome. We are a short drive away from some of the best beaches in the country, amazing kayaking, biking and hiking trails. Minutes from downtown and blocks from the water.

Guest favorite

A spacious bed is neatly made with a textured white coverlet. Decorative pillows feature the words 'Happy' and 'Family' in soft hues. Two bedside lamps with gray shades are placed on wooden nightstands, complementing the calming, light-colored walls.

Guesthouse in Sarasota

4.95 out of 5 average rating, 290 reviews

Siesta Breeze, adorable New Beach Style Studio !

Stay at our renovated beautiful beach styled studio furnishing with a queen size bed as well as a full pull out couch bed. There’s a mini fridge, a two burner electric cooktop, a microwave, a toaster, a tea pot with complementary tea bags, coffee pot with complementary coffee and keurig with complementary Starbucks k cups. Free wifi and a 50 inch tv facing the bed. 2 minutes away from the air port, 10 minutes away from IMG Academy , 30 minutes from Anna Maria Island and siesta key .

Guest favorite

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guesthouse in Sarasota

4.88 out of 5 average rating, 221 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Top guest favorite

A welcoming living area features a light gray couch paired with a modern red accent table. Three large windows allow natural light to fill the space, while indoor plants and decorative items add life. A comfortable chair and a flat-screen TV complete the cozy setting.

Guest suite in Sarasota

4.94 out of 5 average rating, 127 reviews

Unique old Florida tropical apartment

Welcome to a 1930's Florida farmhouse minutes from the gulf. This updated attached private suite has a style all its own. Conveniently located to enjoy the best of both Sarasota and Bradenton, 15 minutes to downtown, St Armands Circle, Lido beach or Village of the Arts. A small boat launch minutes away, is perfect for launching a kayak or paddle board. There are no additional cleaning fees and as a resident host, I am available 24/7 for any questions that may arise.

Guest favorite

A cozy sleeping area is presented with a spacious bed dressed in crisp white linens. Bright orange accent pillows and a matching throw blanket add a pop of color. Soft lighting is provided by wall sconces, positioned on either side of the bed, enhancing the comfort of the space.

Camper/RV in Bradenton

4.89 out of 5 average rating, 102 reviews

RV Free Spirit – Romantic Nature Retreat

🏡 RV Free Spirit Escapa de la rutina y conéctate con la naturaleza en este RV acogedor, diseñado para brindarte comodidad, paz y libertad. Ubicado en un entorno tranquilo, RV Free Spirit es ideal para parejas, viajeros solitarios o cualquier persona que desee relajarse bajo el cielo abierto. 📍 Ubicación privilegiada: • A solo 10 minutos de la prestigiosa IMG Academy • A 20 minutos de las hermosas playas de Anna Maria Island, ideales para disfrutar del sol y el mar

Superhost

A charming house exterior is showcased, featuring large windows that allow ample natural light. A screened porch provides a comfortable entrance, and palm trees surround the property, enhancing the tropical ambiance. The well-maintained driveway leads to the front door of the inviting residence.

Home in Sarasota

4.78 out of 5 average rating, 104 reviews

Cute Bohemian House in quiet, gated community

This cute little house has 2 bedrooms as well as a sleeper sofa. There is also a pack n play for your little ones. All bed and bath linens are provided. There is a fully stocked kitchen with all the basic necessities As well as a dining area and sitting room. There is free wifi and ROKU TV. Guests are also welcome to use the washer and dryer. If you are looking for a fun getaway in a quiet, laid back community this is the perfect place for you.

Guest favorite

A single-story home is depicted, featuring a light-colored facade and a two-car garage. Lush green grass surrounds the property, with palm trees partially framing the view. The sky is filled with fluffy clouds, enhancing the welcoming appearance of the residence.

Home in Sarasota

4.86 out of 5 average rating, 170 reviews

The Sea is Calling

Our home, The Sea is Calling, is located on a cul de sac in Whitfield Estates. It is a short drive to many world class beaches and attractions like Lido Beach, Siesta Key, Longboat Key, Mote Marine, Ringling Museum and Sarasota Jungle Gardens. Our home is welcoming and we hope you decide to let us share a bit of paradise with you. When The Sea is Calling, you must go! We hope to see you soon.