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Holiday rentals in Longboat Key

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Quick stats about holiday rentals in Longboat Key

  • Total holiday rentals

    Explore 1,000 holiday rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 11,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    770 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 180 rentals that welcome pets

  • Holiday rentals with a pool

    830 properties feature pools

  • Rentals with dedicated workspaces

    340 properties have a dedicated workspace

  • Wifi availability

    980 of Longboat Key holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

Top-rated holiday rentals in Longboat Key

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

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Top guest favourite
The exterior of the beach house is depicted, showcasing a blue structure with a metal roof surrounded by tropical landscaping. A gravel driveway leads to the entrance, flanked by palm trees and vibrant foliage, emphasizing the inviting coastal atmosphere.
Home in Longboat Key
4.97 out of 5 average rating, 106 reviews

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

Top guest favourite
Flat in Longboat Key
5 out of 5 average rating, 23 reviews

Cozy private beach condo

Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enjoy breakfast, lunch or dinner with the beautiful view of the Golf of Mexico right from your lanai. This lovely condo has 2 bedrooms 2 bath with small office and full equipped kitchen. The condo is located in a second floor accessible by stair and just a short walk to the complex 600 feet of white sand beach front, heated pool and bbq area. Minimum of 2 week rental available

Superhost
Home in Longboat Key
4.86 out of 5 average rating, 140 reviews

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Guest favourite
A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable green bench is positioned at the foot of the bed. Natural light fills the room through multiple windows adorned with bamboo shades, while a television and dresser complete the space.
Townhouse in Longboat Key
4.84 out of 5 average rating, 44 reviews

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

Kick back and relax in this calm, stylish space. In Cedars East, across from beach AND on the bay. Sleeps 6 - california king master & double bed upstairs. All new carpets upstairs and full laundry in the unit too! Lovely enclosed balcony overlooking trees and boardwalk. Couple of trek bikes available - 10 min walk/ 3 min cycle to beach. Large shared swimming pool, tiki bar, fitness center, tennis on site. Jetty, boardwalk & walk paths. Excellent location, pets allowed. RRR-00819. 2023

Top guest favourite
Apartment in Longboat Key
4.98 out of 5 average rating, 242 reviews

Island Time: Open July 7 - 10!

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 favourite
Flat in Longboat Key
5 out of 5 average rating, 28 reviews

Is this Heaven? No, it's Longboat Key

Newly renovated (November 2025) modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

Top guest favourite
A bright living area is showcased, featuring a light-colored sectional sofa and an accent chair. A large flat-screen TV is mounted on a stylish entertainment unit. Decorative elements include soft textiles and natural light streaming in from multiple windows, enhancing the open-concept layout.
Flat in Longboat Key
5 out of 5 average rating, 14 reviews

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

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.
Apartment in Longboat Key
4.89 out of 5 average rating, 227 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.

Top guest favourite
Apartment in Longboat Key
4.98 out of 5 average rating, 100 reviews

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

Guest favourite
Home in Longboat Key
4.89 out of 5 average rating, 19 reviews

Dog friendly LBK home with deeded access to beach!

**Calendar not always up to date. Please message me for specific dates. Newly renovated 3/2. Location, location, location. Walk or ride bikes to some of the top restaurants on LBK. Perfect for a small family or two couples. Beautiful outdoor screened in porch with grill, couches, dining room set and and ping ping table, outdoor living at its best. Tenants also get to enjoy Cedar’s Racquet Club membership with pool, tennis, pickle ball, full gym and bikes.

Guest favourite
Two light blue adirondack chairs and a small table are positioned by a dock along the intercoastal waterway. The clear sky and calm water reflect greenery and colorful coastal homes in the background, creating a relaxing outdoor setting.
Villa in Longboat Key
4.92 out of 5 average rating, 12 reviews

Waterfront Condo, Close to Beach, with Boat Dock!

BEACH, BOAT, BIKE, FISH, KAYAK, TV/SPORTS, ENTERTAINMENT, FOOD, RELAX & ENJOY! Nestled between the highly sought after Anna Maria Island and St. Armand's Circle this amazing Longboat Key Boathouse offers just as much enjoyment as it does relaxation. This direct waterfront ground floor condo, packed with amenities, is just minutes away from the Gulf of Mexico. Come walk out of your back door to the intercoastal waterway, fish or sit and enjoy the tranquility.

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.
Apartment in Longboat Key
4.97 out of 5 average rating, 71 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.

Popular amenities for Longboat Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Longboat Key's top sights

Img Academy

94 locals recommend

Mote Marine Laboratory

899 locals recommend

St Armands Circle

641 locals recommend

Other great holiday rentals in Longboat Key

Top guest favourite
Flat in Longboat Key
5 out of 5 average rating, 16 reviews

Just renovated, beach view from balcony Unit 203

Guest favourite
A bungalow exterior is depicted, featuring vibrant turquoise stucco walls under clear blue skies. Tropical palm trees provide shade near the entrance. Outdoor seating is visible, including a small table and chairs, surrounded by gravel and greenery, enhancing the island ambiance.
Apartment in Longboat Key
4.95 out of 5 average rating, 19 reviews

Longboat Key Bungalow

Home in Longboat Key
5 out of 5 average rating, 4 reviews

FoxSea Beach Cottage Longboat key Gulf Sunset walk

A light-filled living area is designed with a soft-tone sectional sofa and an armchair, complemented by a textured area rug. A coastal-themed artwork hangs above the sofa, and large sliding glass doors offer scenic views of the beach and ocean beyond.
Apartment in Longboat Key
5 out of 5 average rating, 6 reviews

LaPlaya 206C Gorgeous views of the Gulf.

Top guest favourite
Aerial view of a wide beach features soft white sand and gentle waves lapping at the shore. The water displays a gradient of turquoise to deep blue, with scattered footprints in the sand. The horizon meets a clear sky, enhancing the open coastal atmosphere.
Flat in Longboat Key
4.95 out of 5 average rating, 60 reviews

Turtle walk - Next to 5 top eats-Beach+Boat parkng

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.
Apartment in Longboat Key
4.92 out of 5 average rating, 26 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

Guest favourite
The exterior of a three-story townhome is displayed, featuring light grey siding and ample windows. A paved driveway leads to a single-car garage. Lush tropical landscaping surrounds the entrance, accentuated by vibrant foliage and palm trees, set against a clear blue sky.
Townhouse in Longboat Key
5 out of 5 average rating, 38 reviews

Updated Townhome, Secluded Beach + Pool

Apartment in Longboat Key
4.8 out of 5 average rating, 5 reviews

Waterfront, Spa/Pool, Private Paradise on LBK!

When is the best time to visit Longboat Key?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$327 SGD$392 SGD$432 SGD$324 SGD$254 SGD$259 SGD$272 SGD$256 SGD$237 SGD$256 SGD$294 SGD$327 SGD
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.

Destinations to explore

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