Vacation rentals in Whitfield

A serene outdoor area features two lounge chairs beside a small table, surrounded by lush palm trees. The clear water of the canal reflects the blue sky, while a screened enclosure contains a swimming pool nearby, creating a tranquil setting for relaxation.

5 out of 5 average rating, 16 reviews

Water's Edge: Charming Canal Oasis

*BOAT DOCK AVAILABLE* Escape to the serene waters of our canal-side retreat in Sarasota! Just minutes from downtown's vibrant entertainment scene and pristine beaches, this cozy haven offers a peaceful retreat. Relax on the dock, take a kayak or paddleboard out, or simply soak up the sun. Explore the city's arts and culture scene, indulge in fresh seafood, or unwind on the beach. This charming retreat is the perfect blend of relaxation and adventure. Book now and experience the best of Sarasota!

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.

5 out of 5 average rating, 3 reviews

Private Tropical Oasis-Pool+Golf+Bocce+Fires+Pets

🌴Sara Bay Base Camp🌴 is a MUST-VISIT private resort property for those who love coastal life with 5-⭐️ amenities - we’re 🐶-friendly too! It's centrally-located & just minutes to Sarasota/Bradenton destinations, including world-renowned beaches/islands, unique state parks/nature preserves, IMG Academy, SRQ ✈️, & others! It's a destination to itself situated on historic Sara Bay Country Club & features prime 🏌🏼‍♂️-watching & stunning sunset views while lounging & enjoying top-notch amenities!

4.97 out of 5 average rating, 38 reviews

Saltwater Siesta Family Oasis w/Pool & Game Room

Saltwater Siesta isn’t just a stay - it’s a feeling. Splash in your private saltwater pool, be together in the fully stocked kitchen made for memory-making, & let the littl's dream big in the underwater-themed bunk cove. With a spacious first floor, 2 king, 2 queen, & 2 twin sized beds, 3 full bathrooms, a sunlit private patio, an outdoor space made for fun, & a game room waiting giggles, this sunny Sarasota gem with mini golf near beautiful beaches, & pickleball, is pure beautiful Florida joy.

4.99 out of 5 average rating, 215 reviews

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

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

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, 371 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.

4.91 out of 5 average rating, 195 reviews

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

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.

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, 187 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.

4.88 out of 5 average rating, 219 reviews

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

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.

4.94 out of 5 average rating, 125 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.

A large outdoor pool is framed by mature tropical landscaping, featuring a clear blue water surface under a bright sky. Lounge chairs are positioned around the pool area, providing ample seating for relaxation and enjoyment.

5 out of 5 average rating, 13 reviews

Backyard Oasis, Dual Master suite, Pool home!

Welcome to your private Sarasota getaway! Nestled in a quiet, charming neighborhood, this beautifully renovated mid-century modern home offers everything you need for an unforgettable stay. With two master suites, a stunning outdoor pool retreat, and a massive screened-in lanai with a dedicated exercise/yoga area, this home is perfect for families, groups, or remote workers looking for relaxation and style.

4.98 out of 5 average rating, 274 reviews

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.

Guesthouse in Sarasota

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 offers. 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.

4.98 out of 5 average rating, 115 reviews

A private stock tank pool is surrounded by a natural bamboo fence and lush greenery. The pool is circular with a green top edge and features clear water. Light-colored stones are arranged nearby on a sandy surface, enhancing the serene outdoor atmosphere.

Guesthouse in Bradenton

Private Stock Tank Pool. Cozy Tropical Stay

Cozy tropical retreat just 4.6 miles from Sarasota Airport and 7 miles from the beach. Perfect for two! Enjoy a private stock tank pool, fully equipped kitchen, comfy bed, fast Wi-Fi, and free parking. Relax in your own peaceful outdoor space and feel the tropical vibe. Ideal for a romantic escape, a beach weekend, or simply to unwind in a unique and private setting.

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Other great vacation rentals in Whitfield

The kitchen features light blue cabinetry complemented by stainless steel appliances. A spacious layout is highlighted by a tiled floor with a checkered pattern. A cozy dining nook with wooden chairs and a table is visible, illuminated by natural light from nearby windows.

5 out of 5 average rating, 3 reviews

BayBreeze Cottage | Sleep 8 | Family Stay Near SRQ

Home in Indian Beach-Sapphire Shores

A light-filled living area features a sleek black sofa adorned with green cushions, paired with a glass coffee table. A colorful bookshelf is positioned against one wall, while large windows with unobstructed views invite natural light and views of the surrounding greenery.

5 out of 5 average rating, 84 reviews

Magical Secluded Retreat

A heated pool is centered in the backyard, reflecting warm hues of a stunning sunset. Surrounding the pool are lounge chairs and an outdoor kitchen area, enhancing the inviting outdoor space. Colorful towels are neatly arranged in a basket, adding a touch of comfort and convenience.

4.92 out of 5 average rating, 13 reviews

Home w/ Pool & Outdoor kitchen! Close to Lido Key

A clear pool reflects the blue sky, featuring colorful inflatable loungers floating on the surface. Surrounding the pool, a covered patio offers ample seating, with sun loungers positioned for relaxation. The tranquil space is enclosed by netting, enhancing a private ambiance.

5 out of 5 average rating, 22 reviews

Sunny Escape with Pool & Hot Tub

5 out of 5 average rating, 6 reviews

A modern studio guest suite is presented, featuring a spacious bed with patterned bedding. A kitchenette and bathroom are visible, along with a wall-mounted television. Mirrors reflect the bright lighting from the ceiling fan, enhancing the room's open feel. A cozy area rug adds comfort.

Guest suite in Sarasota

YC Tropical stay W/private entrance and patio

4.95 out of 5 average rating, 385 reviews

The primary suite features warm wood paneling and a spacious bed adorned with a textured blanket. Two nightstands with lamps are placed beside the bed. Natural light enters through two large windows, showcasing lush greenery outside. Soft curtains frame the windows, adding to the room's charm.

Guest suite in Sarasota

FL Mid-Century Hideaway (Full Bath+Outdoor Shower)

A colorful collage showcases various outdoor and indoor spaces. The upper section features a volleyball and mini golf court, nestled alongside a bright outdoor kitchen. The lower segment reveals the game room, equipped with a pool table and lounging area, emphasizing a vibrant and playful design.

5 out of 5 average rating, 3 reviews

Family Fun•Sleeps 14•GameRoom•Near Beaches,SRQ,AMI

A vibrant pool area is surrounded by colorful adirondack chairs in shades of green, blue, yellow, and pink. The sparkling blue water features a gentle fountain, while palm trees add a touch of greenery, creating a lively outdoor relaxation space.