Some info has been automatically translated. Show original language

Vacation rentals in Longboat Key

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Longboat Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
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
4.91 out of 5 average rating, 199 reviews

Beachfront condo in paradise with hot tub AMI

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, 108 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.

Guest favorite
A quaint beach house is surrounded by lush greenery and palm trees, featuring a sandy front yard. A wooden deck with two blue chairs offers an inviting spot for relaxation. The house showcases a cheerful yellow exterior, complemented by vibrant landscaping.
Home in Longboat Key
4.91 out of 5 average rating, 124 reviews

Longboat Key Beach House

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. A 3 minute walk to the beach and to the bay, this house is within a block of restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has 10 HarTru Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Only Minutes to Holmes, Bradenton and Coquina Beaches.

Top guest favorite
A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.
Bungalow in Indian Shores
4.96 out of 5 average rating, 171 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

Top guest favorite
Condo in Longboat Key
4.99 out of 5 average rating, 166 reviews

Silver Sands By the Sea: Open Tonite $100/nt+Fees!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Top guest favorite
Home in Holmes Beach
4.94 out of 5 average rating, 119 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Top guest favorite
Guest suite in Cove
4.93 out of 5 average rating, 281 reviews

Kayak w/ Dolphins - Private Entrance Studio

Paddle with dolphins in Palma Sola Bay from this private-entrance, 2-room studio with living room, bedroom w/ queen, bathroom, food prep area (no kitchen sink). Two TVs, WIFI. Dock access in back yard includes use of kayaks/canoe or docking your boat. Quiet on dead-end street. Owner lives in back of house facing canal (see photo). Your space is private with a tropical street entrance & access to the back yard. Non-shedding dog considered with prior approval.

Top guest favorite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Condo in Siesta Key
4.97 out of 5 average rating, 348 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Top guest favorite
A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.
Guesthouse in Bradenton Beach
4.99 out of 5 average rating, 197 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three 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
Condo in Longboat Key
4.89 out of 5 average rating, 122 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 unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

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
4.86 out of 5 average rating, 192 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.ﺇ716ﺩ.ﺇ808ﺩ.ﺇ914
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Frequently Asked Questions

  • What types of vacation rentals are available in Longboat Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Longboat Key. From over 10 villa rentals, over 460 condo rentals to over 230 house rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Longboat Key?

    Yes! Work meets play with ease at over 350 vacation rentals in Longboat Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Longboat Key?

    Four-legged friends are welcome in Longboat Key. Choose from more than 170 vacation rentals for guests traveling with pets.

  • Are there Longboat Key condo rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 430 condo rentals with pools in Longboat Key, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in condo rentals in Longboat Key?

    Experience the best of Longboat Key with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Longboat Key have a bbq area?

    Absolutely! We offer over 80 condo rentals with a bbq area in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have a gym?

    Absolutely! We offer over 130 condo rentals with a gym in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have self check-in?

    Absolutely! We offer over 40 condo rentals with self check-in in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have free parking?

    Absolutely! We offer over 450 condo rentals with free parking in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly condo rentals in Longboat Key?

    Longboat Key has more than 350 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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 930 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 10,870 verified reviews to help you choose

  • Family-friendly vacation rentals

    720 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 170 rentals that welcome pets

  • Vacation rentals with a pool

    780 properties feature pools

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Wi-Fi availability

    920 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

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key