Holiday houses in Longboat Key

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Longboat Key

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

%{current} / %{total}1 / 1
Top Guest favourite
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 favourite
A spacious sleeping area features a plush king bed with silky white linens and decorative blue accents. A blue ottoman sits at the foot of the bed, while a large TV is placed on a dark wood dresser. Natural light filters in through the nearby balcony doors.
Condo in Longboat Key
5 out of 5 average rating, 11 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

Welcome to paradise - your tropical escape awaits! Wake up to island serenity in our brand NEW studio suite where you'll enjoy peaceful lagoon views from your private balcony. This gem, located in the coveted Longboat Key Resort Club, beautifully blends modern touches with coastal charm. Bask under the sun and enjoy private access to Longboat Key Beach and the heated resort pool which is just steps away. Perfectly positioned for relaxation, adventure, and exploring the best of Downtown Sarasota.

Top Guest favourite
An expansive view of a sandy beach stretches along a turquoise coastline. Gentle waves lap at the shore, and the horizon meets the sky in a blend of blue hues. Sparse greenery frames the edge of the beach, creating a serene and natural environment.
Apartment in Longboat Key
5 out of 5 average rating, 50 reviews

Turquoise Gem 1st Floor

Private beach access! *Designer Renovation* Single level, 4 min walk to bright white quartz sand. Welcome to UPGRADED beach paradise featuring: NEW full Stainless-Steel kitchen, NEW cabinets and granite countertops. LUXURY bathroom with granite top vanity, oversized shower tile with glass Mosaic Inlay and full glass enclosure. 65 inch 4k Roku Smart TVs with Super Fast 1000 MbPs internet. Very Posh Bedroom, KING SIZE Memory Foam Hybrid Bed. Pull-out QUEEN Size Memory Foam Bed in the living room.

Guest favourite
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 favourite
A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.
Condo in Longboat Key
4.98 out of 5 average rating, 222 reviews

Sun-Kissed Memories!

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...!

Guest favourite
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 favourite
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 favourite
Condo in Longboat Key
4.88 out of 5 average rating, 126 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 favourite
An enclosed terrace features a dining table surrounded by white chairs, offering expansive views of Sarasota Bay. Palm trees sway gently outside, while boats are visible in the distance. Natural light floods the space through large glass windows, creating a serene atmosphere.
Condo in Longboat Key
4.97 out of 5 average rating, 70 reviews

Secluded Bayside Gem with beautiful bay views

Sat to Sat Check in/out 7 day minimum rentals only. Jan-April we do not accept reservations with children of any age. Additional 6% Manatee County tax not included need to collect separately. Newly added Pickleball courts on premises. This secluded, beautifully decorated, bay front condo has expanded views of the Sarasota Bay. 2 min drive to the quiet, unspoiled white sand beaches of the Gulf of Mexico, short distance to great water front dining.

Top Guest favourite
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.

Top Guest favourite
A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.
Apartment in Arlington Park
4.97 out of 5 average rating, 197 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

Top Guest favourite
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.
Home in Indian Beach-Sapphire Shores
4.99 out of 5 average rating, 100 reviews

Magical Secluded Retreat

Light-filled mid-century gem, newly renovated with cathedral ceilings. A lush canopy of tropical plants and trees offers privacy and calm unusual for its central location in Sarasota's historic neighborhood on the Bay. Relax inside and out, and lose yourself in birdsong, gently swaying bamboo and beautiful nature. Just 10 minutes to world-renowned beaches and even closer to dining, shopping and museums.

Popular amenities for Longboat Key holiday rentals

When is the best time to visit Longboat Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$403 NZD$457 NZD$458 NZD$418 NZD$328 NZD$334 NZD$351 NZD$331 NZD$306 NZD$331 NZD$380 NZD$423 NZD
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 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.

Quick stats about holiday rentals in Longboat Key

  • Total holiday rentals

    Explore 1,010 holiday rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 11,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    780 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 170 rentals that welcome pets

  • Holiday 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 holiday 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