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Vacation rentals in Longboat Key

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Top-rated vacation rentals in Longboat Key

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Top guest favorite
Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.
Apartment in Longboat Key
4.96 out of 5 average rating, 114 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

Top guest favorite
A large window reveals a stunning view of the sunset over the Gulf. Two red adirondack chairs are positioned to face the ocean, inviting relaxation. The soft glow of the setting sun reflects on the water, creating a serene atmosphere in the living space.
Condo in Bradenton Beach
4.92 out of 5 average rating, 206 reviews

Beachfront Anna Maria Island w hot tub & Gulf view

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

Guest favorite
Condo in Longboat Key
4.88 out of 5 average rating, 111 reviews

Beachfront Escape – Private Balcony, Gulf Views

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

Top guest favorite
Apartment in Sarasota
5 out of 5 average rating, 238 reviews

Luxurious Private Apartment in a House Near Siesta

Large modern construction 950 sq ft 1 bedroom apartment. Beautifully furnished apartment attached to the side of the main house. This upstairs unit has a private entrance with a modern interior & high ceilings. The apartment offers 1 King bed, full kitchen, a bathroom w shower, a washer and dryer, 2 tvs. Nestled on a quiet street with easy access to Siesta Key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key on . Guest must be able to climb one flight of stairs

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, 257 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

Top guest favorite
Condo in Longboat Key
4.98 out of 5 average rating, 222 reviews

Oceanfront LBK: Relax & Recharge!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Top guest favorite
A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.
Condo in Siesta Key
5 out of 5 average rating, 141 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

Top guest favorite
Cottage in Bradenton Beach
4.97 out of 5 average rating, 226 reviews

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Guest favorite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Condo in Longboat Key
4.9 out of 5 average rating, 206 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Guest favorite
Apartment in Bradenton Beach
4.91 out of 5 average rating, 137 reviews

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Guest favorite
Condo in Longboat Key
4.88 out of 5 average rating, 125 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

Top guest favorite
An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.
Condo in Longboat Key
4.87 out of 5 average rating, 195 reviews

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

Popular amenities for Longboat Key vacation rentals

When is the best time to visit Longboat Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ885ﺩ.ﺇ1,003ﺩ.ﺇ1,006ﺩ.ﺇ918ﺩ.ﺇ720ﺩ.ﺇ735ﺩ.ﺇ771ﺩ.ﺇ727ﺩ.ﺇ672ﺩ.ﺇ727ﺩ.ﺇ834ﺩ.ﺇ929
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Frequently Asked Questions

  • What are the best places to stay in Longboat Key?

    Guests often look for vacation rentals near the Gulf beaches or around the bay side for convenient access to water activities and dining. The north and south ends of the island are frequently suggested for their laid-back atmosphere and scenic views.

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

    Families frequently explore the beaches for shell collecting and gentle waves, walk the nature trails at Joan M. Durante Park, or try paddleboarding in calm waters. Many local restaurants have kid-focused menus and outdoor seating.

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

    Enjoy white sand beaches, explore the natural habitats at Joan M. Durante Park, or rent a kayak for a peaceful paddle along the shoreline. The island’s local restaurants and small galleries also capture the coastal community’s character.

  • How is the weather in Longboat Key?

    Longboat Key has mild winters around 51–72°F (10–22°C), with spring bringing warmer, pleasant days. Summers become hot and humid, reaching up to 91°F (33°C), and occasional rainfall is common from late spring through early autumn.

  • When is the best time to visit Longboat Key?

    Late winter through spring is often recommended for dry, mild weather with temperatures around 55–83°F (13–28°C). Summer and early autumn bring higher humidity and rainfall, but also lush landscapes and fewer crowds.

  • What are the best places to visit in Longboat Key?

    The island has scenic beaches, the Joan M. Durante Park with its boardwalks and gardens, and a lively waterfront area with local shops and restaurants. Exploring the bay by kayak or paddleboard is also frequently suggested.

  • What are some hiking trails in Longboat Key?

    Explore the Joan M. Durante Park trails, which wind through native gardens and mangrove forests, or wander the pathways at local preserves for birdwatching and views of Sarasota Bay. Trails are generally flat and suitable for all ages.

  • What are some family activities we can do in Longboat Key?

    Families often enjoy shelling on the beach, picnicking at local parks, or spotting wildlife along the trails at Joan M. Durante Park. Guided kayak tours and casual bike rides are also popular with visitors of all ages.

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

    Explore nearby Sarasota's art museums or lively downtown, visit historic fishing villages around the area, or discover the natural beauty of nearby nature preserves. Barrier islands and gardens just outside Longboat Key are also often recommended.

  • Are there any pet friendly accommodations available in Longboat Key?

    Many vacation rentals on Longboat Key welcome pets, particularly in beachside cottages and private homes. Local parks and outdoor dining spaces often include dog-friendly areas, making it easy to explore together.

  • What are some local tips for visiting Longboat Key?

    Consider bringing sun protection and reusable water bottles, as much of life on Longboat Key happens outdoors. Many shops and restaurants have a relaxed dress code, and exploring the island by bike is often recommended for a leisurely pace.

  • What is Longboat Key known for?

    Longboat Key is known for its tranquil Gulf beaches, locally inspired seafood, and serene natural preserves like Joan M. Durante Park. The island has a relaxed atmosphere, often attracting those looking for a coastal retreat.

  • What are the best hidden gems to explore in Longboat Key?

    Seek out quiet beach access points for peaceful shoreline walks, or visit local nature preserves with boardwalks through mangroves. Art galleries and small family-run restaurants around the island often highlight coastal traditions.

  • What are the best foods to try in Longboat Key?

    Longboat Key is known for fresh seafood like grouper sandwiches, stone crab, and shrimp prepared with local flavors. Key lime pie is a frequently suggested dessert, and many spots feature locally sourced produce and citrus.

  • What should I bring for a trip to Longboat Key?

    Pack swimwear, light layers, comfortable sandals, and sun protection such as sunglasses and a hat. A reusable water bottle and beach gear like a towel or snorkel set can help you make the most of the coastal setting.

  • What is the nightlife in Longboat Key like?

    Longboat Key has a relaxed nightlife scene, with waterfront bars, live music at local restaurants, and venues that feature sunset views. Many visitors enjoy low-key evenings and outdoor lounges rather than late-night clubs.

  • What are the most popular events or festivals in Longboat Key?

    Seasonal art fairs, seafood festivals, and holiday boat parades are frequently suggested activities in and around Longboat Key. Community markets and cultural events often take place during the cooler months.

  • Are there family friendly vacation rentals in Longboat Key?

    Longboat Key has a variety of family friendly vacation rentals, including multi-bedroom homes, condos with pools, and properties near beaches or parks. Kid-focused amenities such as full kitchens and outdoor spaces are commonly available.

All about Longboat Key

Stretching between the Gulf of Mexico and Sarasota Bay, the barrier island of Longboat Key has attracted its share of sun-seekers, who can be found teeing off at the sweeping gulf-front golf courses or fishing in the mangroves for speckled trout. With Siesta Key to the south and Anna Maria Island to the north, Longboat Key has an upscale feel, with nice restaurants, luxury resorts, and 256 days of annual sunshine. At the northern tip is Beer Can Island, a popular picnic spot that’s prettier than its name might suggest; the untouched, white-sand beach is even accessible on foot at low tide. Paddleboarding, windsurfing, and other on-the-water activities beckon you into the Gulf. And when you’ve finally kicked the sand from your toes and are ready for some culture, you can visit the Ringling Museum of Art in Sarasota, which showcases the circus impresario’s vast collection of classic and modern European and American artworks.

What are the top things to do in Longboat Key?

St Armands Circle

This round little island shopping center just south of Longboat Key is home to high-end boutiques, art galleries, fine dining, and other urbane attractions. Surrounded by water on all sides, it makes for a perfect scenic day of shopping. Check the calendar for special events throughout the year.

Coquina Beach

Just a few minutes’ drive over the Longboat Pass Bridge, this relaxed white-sand beach at the southern end of Anna Maria Island is worth a visit for its scenic sunset views. Hunt for shells, play some beach volleyball, and keep an eye out for passing pods of dolphins.

Quick Point Nature Preserve

A short (0.8-mile) walking trail wends its way through 34 acres of protected wetlands and mangrove lagoons. If you’re lucky you might spot a dolphin swimming through the seagrass, or watch a heron, egret, or ibis hunting for its dinner.

Quick stats about vacation rentals in Longboat Key

  • Total vacation rentals

    Explore 1,010 vacation rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 11,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    780 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 170 rentals that welcome pets

  • Vacation rentals with a pool

    830 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wi-Fi availability

    990 of Longboat Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises, and Beachfront across Longboat Key rentals

  • 4.8 Average rating

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

Destinations to explore

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