Holiday houses in Longboat Key

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Top-rated holiday rentals in Longboat Key

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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, 115 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
Townhouse in Anna Maria
4.98 out of 5 average rating, 121 reviews

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

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 private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.98 out of 5 average rating, 164 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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, 98 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

Guest favourite
Home in Longboat Key
4.86 out of 5 average rating, 138 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

Top Guest favourite
Condo in Longboat Key
4.98 out of 5 average rating, 227 reviews

Sun-Kissed Memories: Open Thursday, $270/nt+Fees!

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 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, 128 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. It’s 1 mile to the beach access and the house is within a block of great restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has Pickleball and Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Minutes to Holmes, Bradenton and Coquina Beaches.

Top Guest favourite
The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.
Home in Bradenton Beach
4.98 out of 5 average rating, 101 reviews

Gulf Front! Beach Views!+ Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

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
4.89 out of 5 average rating, 208 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
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

*Designer Renovation* Single level, next 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, 127 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.

Popular amenities for Longboat Key holiday rentals

When is the best time to visit Longboat Key?

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Avg. price$413 NZD$468 NZD$470 NZD$429 NZD$336 NZD$343 NZD$360 NZD$340 NZD$314 NZD$340 NZD$389 NZD$434 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 $51 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, 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!

Destinations to explore

  1. Airbnb
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  3. Florida
  4. Manatee County
  5. Longboat Key