Vacation rentals in Whitfield

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Top-rated vacation rentals in Whitfield

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Top guest favorite
Home in Sarasota
5 out of 5 average rating, 27 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!

Top guest favorite
Home in Sarasota
4.94 out of 5 average rating, 108 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.

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, 211 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.

Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 29 reviews

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

Get ready for nonstop fun at Paradise Island - an amenity-packed retreat in Sarasota! Whether you're in the heated pool or hot tub, playing mini golf, enjoying a family game night, relaxing by the fire pit, or grilling barbecue in the backyard, there’s something here for everyone. This vibrant 4-BR, 2-bath home sleeps up to 14 guests and is just 5 minutes from the airport and a short drive to world-class beaches. BOOK YOUR STAY TODAY - The Ultimate Retreat for Family Fun and Forever Memories

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, 276 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

Guest favorite
A collage showcases key areas of the property, including a spacious pool area with loungers, a game room equipped with a pool table and foosball, a cozy living room with a fireplace, and an outdoor space featuring a relaxed atmosphere surrounded by greenery.
Home in Sarasota
4.92 out of 5 average rating, 50 reviews

Sarasota Oasis: Convenient/Heated Renovated Pool

Welcome to Coastal Serenity, your perfect Sarasota escape! This charming, fully remodeled coastal home is designed with relaxation and fun in mind. Just three blocks from the breathtaking Sarasota Bay and only a few miles from stunning beaches like Siesta Key, Lido Key, Bradenton Beach, and Anna Maria Beach, it’s an ideal location for beach lovers. Plus, you’re only steps away from vibrant tiki bars and luxurious Sarasota restaurants, perfect for unwinding in a relaxed, inviting atmosphere.

Guest favorite
Condo in Sarasota
5 out of 5 average rating, 9 reviews

Sarasota Studio | Heated Pool | Near Siesta Key

Coastal marina calm meets boutique hotel vibes on Sarasota Bay. This privately owned studio condo is located within a hotel property and operates as an independent Airbnb unit. Sleeping arrangement includes a queen bed and sofa sleeper in the studio. Minutes from beaches & IMG. Hidden gem. Located on Ramada By Wyndham property with bar, boat rentals, pool and 3 minutes from SRQ. Perfect for IMG coaches, athletes, and travelers. Private jet services nearby. Sunset Views and free parking.

Guest favorite
The studio features a cozy seating area with a blue couch, complemented by decorative throw pillows. A queen size bed is positioned against a light wall, with sliding barn doors leading to a closet. A kitchenette with modern appliances is visible in the corner.
Guesthouse in Sarasota
4.95 out of 5 average rating, 325 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
Home in Sarasota
4.98 out of 5 average rating, 105 reviews

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

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
4.93 out of 5 average rating, 148 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 bright living space features a large window allowing natural light to fill the room. A modern coffee table sits atop a striped rug, with a sleek TV mounted on the wall. Decor items and a welcoming door can be seen in the background.
Home in Sarasota
4.97 out of 5 average rating, 104 reviews

Lovely Home by 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!

Guest favorite
A single-story home is surrounded by lush landscaping and palm trees, set against a vibrant sunset sky. The entrance features well-kept plants and a paved driveway leading to the garage. The spacious front yard is meticulously maintained, offering ample green space.
Home in Sarasota
4.98 out of 5 average rating, 41 reviews

The Palm House: cozy, safe, central Sarasota

Thank you for considering my home in Sarasota for your accommodations! Whether you're looking for a home close to IMG, the SRQ airport, a short drive from Sarasota's barrier islands and thriving downtown or seeking a cozy family home look no further. With my 15+ year background in hotels and hospitality I designed this space to be welcoming, playful and comfortable for all visitors. I look forward to hosting you in Sarasota!

Popular amenities for Whitfield vacation rentals

When is the best time to visit Whitfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$35,212 GYDG$38,566 GYDG$38,566 GYDG$31,230 GYDG$26,200 GYDG$26,200 GYDG$28,925 GYDG$26,200 GYDG$25,990 GYDG$27,038 GYDG$30,182 GYDG$31,859 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Frequently Asked Questions

  • What are the best places to stay in Whitfield?

    Stays near neighborhood parks, the waterfront, or the historic district are frequently suggested for a relaxing visit to Whitfield. Many accommodations in the greater Sarasota-Bradenton area provide a mix of quiet, scenic settings and convenient amenities.

  • What are the best things to do in Whitfield with kids?

    Children can enjoy playgrounds, splash areas, and spotting wildlife in local parks near Whitfield. Hands-on activities at nature centers or small museums in the greater area are often suggested for families.

  • What are some of the best things to do in Whitfield?

    Whitfield has peaceful waterfront spaces, public parks, and chances for kayaking or paddleboarding on the bay. Art galleries, local eateries, and nature trails around the area also provide inviting options for visitors.

  • How is the weather in Whitfield?

    Whitfield has warm, humid summers around 90°F (32°C), and mild winters near 70°F (21°C), with more rainfall in summer months. Lightweight, breathable clothing and rain gear are useful throughout much of the year.

  • When is the best time to visit Whitfield?

    Late winter through early spring is often recommended for mild, sunny weather around 70–80°F (21–27°C), with lower rainfall. Early fall can also bring pleasant temperatures and local festivals.

  • What are the best places to visit in Whitfield?

    Many guests explore local parks, public waterfronts, and the neighborhood’s historic districts. Art galleries, golf courses, and markets around Whitfield also create inviting stops for travelers.

  • What are some hiking trails in Whitfield?

    Whitfield has walking paths in neighborhood parks and nature preserves, often frequented by birdwatchers and those seeking bay views. For more extensive hikes, consider exploring established coastal trails in parks nearby.

  • What are some family activities we can do in Whitfield?

    Families frequently enjoy playgrounds, picnics at local parks, and birdwatching near the bay in Whitfield. Interactive nature centers and small museums around the area provide engaging options for all ages.

  • What are some of the best day trip ideas from Whitfield?

    You can explore white sand beaches nearby, visit lively art scenes in Sarasota or Bradenton, or spend a day at wildlife preserves in the region. Local aquariums and botanical gardens around the Gulf Coast are often suggested for varied interests.

  • Are there any pet friendly accommodations available in Whitfield?

    Many homes and rentals in Whitfield welcome pets, especially those located near green spaces or walking paths. Nearby neighborhoods also have options for guests traveling with dogs or other pets.

  • What are some local tips for visiting Whitfield?

    Consider lightweight clothing and sun protection for the warm, humid climate, and bring a reusable water bottle. Exploring community markets or waterfront parks around Whitfield is often recommended by locals who enjoy a relaxed pace.

  • What is Whitfield known for?

    Whitfield is known for its quiet residential character, bayfront views, and established neighborhoods. It serves as a gateway to the cultural attractions, golf courses, and natural beauty found in the greater Sarasota-Bradenton area.

  • What are the best hidden gems to explore in Whitfield?

    Small community preserves, quiet nature trails, and local art studios around Whitfield are frequently considered hidden gems. You may also find lesser-known cafes or historic spots that reflect the area’s character.

  • What are the best foods to try in Whitfield?

    Whitfield has many coastal Florida influences, so seafood dishes like grouper sandwiches, shrimp, and mullet are frequently suggested. You might also find Cuban sandwiches, key lime pie, and Southern comfort foods at local restaurants.

  • What should I bring for a trip to Whitfield?

    Pack light layers, a wide-brimmed hat, and sunscreen for the warm, sunny weather. Comfortable walking shoes are helpful for exploring parks, and many visitors bring insect repellent for outdoor activities.

  • What is the nightlife in Whitfield like?

    Nightlife in Whitfield tends to be low key, with a focus on casual dining, neighborhood pubs, and community gatherings. For more vibrant evening entertainment, guests often explore local venues and music scenes in Sarasota or Bradenton.

  • What are the most popular events or festivals in Whitfield?

    Around Whitfield, regional art fairs, seasonal food festivals, and community gatherings are frequently suggested, especially in spring and fall. Larger cultural events in Sarasota and Bradenton draw many visitors throughout the year.

  • Are there family friendly vacation rentals in Whitfield?

    You will find a selection of family-friendly vacation rentals in Whitfield, many with features like multiple bedrooms, kitchens, and nearby parks. These properties often appeal to guests seeking a relaxed, residential setting.

Quick stats about vacation rentals in Whitfield

  • Total vacation rentals

    Explore 180 vacation rentals in Whitfield

  • Nightly prices starting at

    Whitfield vacation rentals start at G$6,288 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,510 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Whitfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Whitfield rentals

  • 4.8 Average rating

    Whitfield stays are highly rated by guests—averaging 4.8 out of 5!

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