Family-friendly vacation rentals in Whitfield

4.93 out of 5 average rating, 129 reviews

Cozy Beach House Including King Size Suite !

Welcome to our beach home ! Located in a beautiful neighborhood where you can unwind & relax with the family after a long day at the beach. We are located only a short drive to the finest beaches in FL where you can find sand dollars with the kids & view breathtaking sunsets ! Play a game of pool, grill out on our patio, & enjoy our fire pit & enclosed pool !! This easy access one-level home sleeps up to 8 people. Conveniently located within minutes from groceries, restaurants, and attractions.

Indoor spacesKitchenAir conditioning

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.

4.82 out of 5 average rating, 224 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 (no cable), 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.

FamilyIndoor spacesHospitality

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.

4.99 out of 5 average rating, 317 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

FamilyIndoor spacesCheckout

5.0 out of 5 average rating, 115 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

FamilyIndoor spacesCondition

A screened patio area features a private heated pool, surrounded by lush greenery. Comfortable seating includes wooden chairs and a table, with lounge chairs positioned by the pool. Bright sunlight fills the space, creating a welcoming atmosphere for relaxation.

4.96 out of 5 average rating, 112 reviews

Htd Pool | PingPong | Foosball | 12 min to Beach

Welcome to Coastal Farmhouse Sarasota! ✨ Your ideal family getaway is just two blocks from Sarasota Bay and minutes from Florida’s most famous beaches Siesta Key, Lido Key, Bradenton Beach, and Anna Maria Island. Designed with families and groups in mind, this newly remodeled 4-bedroom home sleeps up to 12 guests and features a screened heated pool, a fully equipped kitchen, and a bright, open layout perfect for relaxing and entertaining. Perfect for families, groups, and beach lovers!

Indoor spacesKitchenWifi

4.93 out of 5 average rating, 113 reviews

Golf View-4BR Htd Pool/Near IMG/AMI/Siesta Beaches

Welcome to The Siesta Retreat located on Sarasota FL. This gorgeous home has been completely renovated in a peaceful area overlooking the Sara Bay Country Club Golf Course . Pack your bags and get ready to vacation! Home is 4 miles from SRQ Airport and 7 miles from downtown Sarasota. Siesta Key has been rated the #1 beach in the US, only 14 miles from the home. Additionally Ana Maria Island is 15 miles, Lido Beach 10 miles, Coquina Beach 13 miles, and Longboat Key 16 miles from home.

Indoor spacesKitchenQuiet

4.95 out of 5 average rating, 350 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 .

FamilyIndoor spacesComfort

The image features a heated saltwater pool with a pink inflatable flamingo. Surrounding the pool are comfortable seating options, including fire pit seating. The vibrant indoor spaces are visible, showcasing a cozy living room with a turquoise color scheme and a game room with a retro arcade machine.

4.98 out of 5 average rating, 110 reviews

Family Oasis *Heated Saltwater Pool *Near Beaches

Welcome to ☀️ Sarasota Sunshine ☀️ — your family's home away from home! Relax by your private heated pool, spend the day at nearby Gulf Coast beaches, or visit downtown Sarasota from our thoughtfully designed home. Sleeping up to 9 guests, Sarasota Sunshine offers modern comfort and extensive family-friendly amenities, making it easy to pack less, relax more, and create lasting memories. Minutes from downtown Sarasota, SRQ Airport, IMG Academy, and world-famous Gulf Coast beaches.

FamilyKitchenWalkability

4.94 out of 5 average rating, 159 reviews

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

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.

Indoor spacesKitchenComfort

4.96 out of 5 average rating, 114 reviews

Lovely House in Sarasota Bay

Enjoy a stylish coastal bungalow in North Sarasota, just minutes from downtown’s restaurants, shops, and Sarasota Bay. Relax in modern comfort with central A/C, high-speed WiFi, and smart TVs in every room. Nearby, explore beaches like Siesta Key, Lido Key, and Anna Maria Island. The fully-equipped kitchen, comfortable bedrooms, and modern bath make for a relaxing stay. Plus, you’re close to top attractions like The Ringling Museum, Marina Jack, and more!

Indoor spacesKitchenCheck-in

A charming one-level home is presented, surrounded by lush tropical landscaping. The exterior features a welcoming entrance with a decorative lantern and a garage, set against a backdrop of a colorful sunset sky, enhancing the inviting atmosphere of the property.

4.96 out of 5 average rating, 129 reviews

Double oven | 4 Famous Beaches | Wine Fridge

Escape to The Bay 218, a beautifully updated one-level Sarasota retreat just steps from the bay and minutes from Lido Key, Siesta Key, Longboat Key, and Anna Maria Island. Relax by your private heated pool, enjoy the chef's kitchen, spacious living areas, and comfortable bedrooms, or head to the beach with the included chairs, cart, and toys. Perfect for families, friends, and coastal getaways. Dog-friendly with approval.

KitchenIndoor spacesBackyard

A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 303 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

KitchenIndoor spacesValue

Popular amenities for Whitfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 142 reviews

Home in South Bradenton

*New |Outdoor Theatre|Heated Pool | HotTub | Games

KitchenFamilyHot tub

4.82 out of 5 average rating, 101 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and decorative rocks. Palm trees and various plants enhance the area, while the tranquil water view is visible in the background, providing a calming atmosphere for relaxation.

Loft in Bradenton

Mediterranean-Type Waterfront w/Pool-Saltwater Spa

Indoor spacesFamilyPool

4.97 out of 5 average rating, 157 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

FamilyIndoor spacesView

A spacious outdoor area features a heated saltwater pool surrounded by a screened enclosure. A jacuzzi is attached to the pool, with multiple lounge chairs positioned for relaxation. Lush greenery lines the perimeter, enhancing the sense of privacy and tranquility.

4.85 out of 5 average rating, 108 reviews

Stylish 6 Bed Pool Home with Golf Simulator & Spa

KitchenFamilyBackyard

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 123 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

FamilyKitchenAccess

4.98 out of 5 average rating, 116 reviews

A spacious pool area is depicted, featuring clear blue water surrounded by a large stone patio. Colorful umbrellas provide shade, while lounge chairs and green Adirondack chairs are positioned for relaxation. Lush tropical plants frame the scene, enhancing the inviting poolside atmosphere.

Apartment in Sarasota

Graceful Getaway

Indoor spacesFamilyShared spaces

4.88 out of 5 average rating, 110 reviews

4BR Private Coastal Retreat: Heated Pool, Near AMI

FamilyKitchenCleanliness

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

4.96 out of 5 average rating, 139 reviews

Waterfront View Mins To AMI Beaches

FamilyIndoor spacesGetting around

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 123 reviews

Beach House by the Bay

FamilyIndoor spacesAmenities

4.84 out of 5 average rating, 119 reviews

LUXE! Heated Salt POOL! Close to Town, Beach, IMG

FamilyKitchenView

The inviting pool area features a vibrant mural, surrounded by tropical greenery. A floating flamingo and watermelon-shaped inflatable add a playful touch to the azure water. Colorful poolside seating, including cheerful yellow chairs, enhances the relaxing atmosphere of this outdoor space.

4.97 out of 5 average rating, 103 reviews

Near IMG! Fun 4BR•Pool w/Golf, Arcade & Fire Pit!

FamilyKitchenBathroom

4.98 out of 5 average rating, 104 reviews

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

Guesthouse in Bradenton

Serenity Lake

KitchenIndoor spacesAccuracy

The exterior of a charming adobe-style home is highlighted, featuring a light blue facade and a decorative entrance. A pathway leads to the door, bordered by colorful plantings and a white picket fence. Tropical plants add to the serene ambiance of the front garden.

4.95 out of 5 average rating, 121 reviews

Casa de Zara| Downtown Sarasota- 5mi Lido Beach

FamilyIndoor spacesAmenities

5.0 out of 5 average rating, 13 reviews

Paradise Escape w/ Pool, Sarasota/Bradenton

FamilyIndoor spacesPool

A private screened pool area features a vibrant blue pool surrounded by loungers and colorful pool floats. A well-maintained lawn and mini-golf area are visible, while a game room with bright visual elements offers entertainment options. A cozy living space showcases a comfortable sofa and artistic wall design.

4.91 out of 5 average rating, 77 reviews

Heated Pool-Near Beaches-MiniGolf-Arcade

KitchenFamilyNearby

4.89 out of 5 average rating, 55 reviews

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

FamilyKitchenNearby

Family-friendly home rentals with a pool

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.

4.8 out of 5 average rating, 126 reviews

Cute Bohemian House in quiet, gated community

KitchenIndoor spacesComfort

5.0 out of 5 average rating, 9 reviews

Home in Bayshore Gardens

King Beds | Game Room | Putt Putt | Pool |

FamilyIndoor spacesCleanliness

A charming yellow cottage is shown surrounded by lush greenery. The exterior features arched windows and a terrace area furnished with blue chairs and a table, complemented by a striped umbrella. Flower arrangements add a touch of color to the vibrant setting.

4.93 out of 5 average rating, 30 reviews

Casita Floreado! Private 1BR cottage, with pool

Indoor spacesKitchenParking

A spacious outdoor area features a clear pool surrounded by lush greenery and palm trees. Lounge chairs are arranged beside the pool, and a playset is visible in the background. Neatly laid stepping stones lead towards the grass, enhancing the inviting environment.

4.97 out of 5 average rating, 93 reviews

As seen on HGTV | 6 miles to the beach! Htd pool

KitchenIndoor spacesParking

5.0 out of 5 average rating, 3 reviews

The Aviator | 7 Mins From SRQ | Pool | Giga Wifi

KitchenFamilyHospitality

A screened-in outdoor area features a sparkling pool surrounded by tan brick pavers. Four white lounge chairs are positioned near the water, and the light blue sky complements the home's beige exterior and vibrant blue doors.

4.92 out of 5 average rating, 92 reviews

4BR Sarasota Retreat | Private Pool & Game Room!

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 38 reviews

Private Heated Pool~Yacht Rental~BBQ~Near Water

KitchenIndoor spacesAccess

The vibrant outdoor space features a mini-golf putting green, surrounded by strategically placed lounge chairs and Adirondack seating. Illuminated by string lights, the heated pool area is complemented by cabana umbrellas, with a backdrop of the house showcasing lively decor and inviting lighting.