Family-friendly vacation rentals in Whitfield

4.95 out of 5 average rating, 367 reviews

A vibrant courtyard is filled with tropical plants, colorful lounge chairs, and a tiki bar. Unique garden decorations and a fish pond with a waterfall enhance the lively atmosphere. Striped umbrellas provide shade over the seating areas, creating a welcoming outdoor space.

Townhouse in Sarasota

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

You are safe with me!Enhanced cleaning protocol in place- as per Airbnb guidelines. Welcome! Be yourself! A five star stay, guaranteed. You WILL be happy here! Special occasion? My favorite. I like doing special things for special people. Courtyard w/ lounge chairs, tiki bar, pond & cafe seating! Queen bed and a pullout couch with new mattress! A 1/2 m walk to downtown. 1 of 2 upstairs apartments at The Tropical Nut! We aim to please! No-regret-booking! Will consider-if asked-pets of all kinds!

The exterior of a single-level home is presented, framed by lush tropical landscaping. A well-manicured lawn leads to a covered entrance, which is adorned with a charming lamp. The property features a two-car garage and a driveway, creating a welcoming access point.

4.97 out of 5 average rating, 100 reviews

Saltwater Pool + Huge Kitchen | Hammock | Open Con

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 oven, wine fridge, pot filler, center island, and granite countertops—perfect for preparing memorable meals together. Two generous living spaces make this home

Superhost

The bedroom features a spacious bed adorned with decorative pillows. A circular rug with vibrant patterns complements the warm wood flooring. A round mirror hangs above a bedside table, and two lamps provide softly diffused lighting. Windows invite natural light into the room.

Guest suite in Indian Beach-Sapphire Shores

4.85 out of 5 average rating, 291 reviews

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as free wifi and parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally! Come relax in Arcadia!

4.97 out of 5 average rating, 276 reviews

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

Guesthouse in Sarasota

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

4.91 out of 5 average rating, 355 reviews

A welcoming entryway features a turquoise door and a decorative 'Welcome' sign. Two chairs with cushions are positioned at a small round table on a wooden deck, inviting relaxation. Nearby, flowers are displayed on a mail holder, completing the inviting exterior.

Cottage in Bradenton

Private King Bed Suite-Near AMI Beach-Walk D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 8:00AM. Please respect others. Walk to many great restaurants!

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.

4.89 out of 5 average rating, 364 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.

Superhost

A pineapple plant is featured prominently in the foreground, with a small pineapple developing. In the background, the house is framed by greenery and a porch with white railings, complemented by soft natural lighting.

4.83 out of 5 average rating, 241 reviews

The Pineapple Suite.Teal tropical home in Sarasota

This is a perfect space for a vacations, snowbirds, visiting professionals (desk and work station within home), or families looking for a home located in the center of Sarasota, Florida. Access everything you need in just a short ride: beaches, University Mall/UTC, hospitals, interstate, gyms, downtown, yoga, local hangouts, and really good food! [*Important note: For all communication, please use the Airbnb App. It is the fastest, most direct and effective way to reach us!]

A covered front porch features two gray Adirondack chairs, set against light blue paneling. A welcoming door with a glass insert leads into the home. Planters with greenery add a touch of color amidst freshly mulched landscaping.

4.97 out of 5 average rating, 100 reviews

"Chill Time” Great Location in Sarasota

Great location, only 1 mile from Downtown Sarasota. Cozy home with a mid-century flair in a quiet neighborhood near downtown Sarasota and minutes from Payne Park and the Legacy Trail. This is a family friendly home with a fenced back yard, close to all the great things Sarasota has to offer- museums, gardens, theaters, and beaches. The home is just a 1.5 miles to Downtown,15 min drive to Lido Beach, and 20 min to Siesta Key. One dog will considered with an added fee.

Home in Indian Beach-Sapphire Shores

A rustic wooden sign with the word 'Welcome' painted in white is displayed prominently. Dried floral arrangements are arranged above the sign, adding a natural touch. A small turquoise glass jar sits nearby, contributing to a warm and inviting entryway.

4.9 out of 5 average rating, 667 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

4.84 out of 5 average rating, 264 reviews

A Ranch-style house with a warm-toned exterior is featured. A concrete driveway leads to a single-car garage. Lush green landscaping surrounds the front yard, where trees provide shade. The entrance is marked by a welcoming door, complemented by windows that allow natural light.

Home in Bradenton

Comfortable & modern house in Central Bradenton

Well maintained Ranch style house (built 2004) in a quiet working class neighborhood near central Bradenton. Easy access to US41 and 301. Close to Lecom Park (Pirates baseball). Keyless entry. Room for 2 cars on driveway. 3 bedrooms. King bed in the MBR, 2 single beds in front bedroom, one single bed in middle room. Sleeper sofa in back living room Full Kitchen. Two Bathrooms with toilet and bathtub. Central AC & Heat Washer & Dryer

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.

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.