Longboat Key Vacation Rentals

Longboat Key Vacation Rentals By Owner

Start searching for luxury Longboat Key beach houses and condos, by owner with pools, beachfront locations, monthly stays and more. Check it out below.

NO REGRETS! Bright luxury SOLAR home. PRIVATE POOL! Quick walk to beach and bay.

Longboat Key Vacation Rentals
4/BR 2.5/BA SLEEPS 8

BEACHPLACE PENTHOUSE - DOUBLE BALCONY FULL GULF & BAY VIEWS!

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 3 – 503 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 3 – 304 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

The Pierre 507 by FGC

Longboat Key Vacation Rentals
2/BR 3/BA SLEEPS 4

Longboat Key Direct Beachfront Penthouse - Beachplace 2-604

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 6

Beachplace 6 – 303 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 4 – 304 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

770 Longboat Ct by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 6

Beachplace 3 – 603 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

NEW LISTING! Longboat Key Monthly Rental - Beachplace 4 -204

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 6

Beachplace 3 – 301 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Promenade 102 by FGC

Longboat Key Vacation Rentals
3/BR 3/BA SLEEPS 6

Beachplace 8-204 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 9 – 501 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 3 – 502 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 3 – 302 by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Beachplace 7 – 202 by FGC - Longboat Key Monthly Beachfront Rental

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4

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Longboat Key Vacation Rentals 

Longboat Key, Florida, is a paradise where pristine beaches meet upscale relaxation. Nestled between the azure waters of the Gulf of Mexico and Sarasota Bay, this idyllic barrier island offers a serene escape for visitors seeking both tranquility and luxury. It runs 10.8 miles long by .5 to 1 mile wide. With its elegant resorts, world-class golf courses, and superb dining options, Longboat Key caters to those looking to unwind in style. Nature enthusiasts will revel in the island's natural beauty, from its lush landscapes to the stunning sunsets that paint the sky each evening. Whether you're strolling along the sandy shores, indulging in water sports, or savoring the local cuisine, Longboat Key promises a refined and rejuvenating coastal retreat.

  • Hosts rent homes for 30 night min stays with check in's usually at the beginning of the calendar month

Check information further below to help your search.

Is Longboat Key a good place to rent a Vacation Rental?

Longboat Key is an exceptional choice for renting a vacation property. This charming barrier island seamlessly blends relaxation and luxury, making it an ideal getaway destination. Whether you're interested in a beachfront condo with captivating views, a lavish villa, or a cozy cottage, Longboat Key offers a diverse selection of vacation rentals to cater to various preferences and group sizes.

The island's unspoiled beaches provide the perfect backdrop for unwinding, engaging in water activities, and admiring stunning sunsets. Additionally, Longboat Key's close proximity to Sarasota grants access to cultural attractions, shopping districts, delectable dining options, and vibrant entertainment scenes, adding to the overall vacation experience.

Whether you're traveling as a couple, a family, or a group of friends, Longboat Key's harmonious blend of natural allure, upscale lodgings, and recreational possibilities ensures a remarkable vacation rental experience that will leave lasting memories.

What do I need to know to rent a vacation home in Longboat Key?

To rent a vacation home in Longboat Key, there are several key aspects to consider for a smooth and enjoyable experience. Begin by researching reputable vacation rental platforms (like FLARBO) or local property management companies that offer properties in the Longboat Key area. Look for homes that match your preferences, whether it's a beachfront condo, a spacious villa, or a cozy cottage.

Check the property's amenities and features to ensure they align with your needs. Be mindful of factors such as the number of bedrooms, bathrooms, kitchen facilities, and any extra perks like a private pool or access to recreational activities.

Carefully review the rental agreement, including terms, pricing, cancellation policies, and any additional fees. Communicate directly with the property owner or manager to clarify any doubts and ensure a transparent understanding of the rental process.

Consider the location – whether you want to be right on the beach, close to dining and entertainment, or in a quieter bayside or village area. It's also wise to read reviews from previous renters to get an idea of their experiences.

Lastly, plan ahead and book your rental well in advance, especially during peak travel seasons. By taking these steps, you can look forward to a memorable and comfortable stay in a vacation home on beautiful Longboat Key.

Typical Stay Periods

Unless a property is classified as a 'grandfathered' tourism use or falls within a designated tourism-zoned area, each rental period must span at least 30 consecutive calendar days, equivalent to a full calendar month, or a longer duration. If the rental period is less than 6 months, the property or unit is required to register with the Town for a Residential Rental Certificate of Registration.

  • weekly
  • monthly
Typical Turnover Day

In Longboat Key, vacation rentals typically follow a Saturday turnover date, especially during peak seasons. However, it's important to note that this turnover day can differ depending on the individual host.

  • Saturday
Longboat Key Vacation Rental Price Information

Low range from $135 per night - $945 per week - $3,780 per month

High range from $3,500 per night - $24,500 per week - $98,000 per month

Booking Window

Longboat Key is a well known snowbird and long term stay location. The best vacation rentals book over 1 year in advance. On average the booking window for this region is 12 months in advance. Make arrangements in advance to secure the property you prefer!

Guest Retention

Many Longboat Key visitors fall in love with Longboat Key with the golf courses, community vibe, gorgeous beaches, upscale restaurants and great boating. Monthly stay visitors are very loyal to this area and return annually for their winter vacations. There are 8,000 full time residents on Longboat Key an additional 12,000 seasonal residents will visit in season according to the Longboat Key Chamber.

High Season

Longboat Key High Season - December to April

The peak months to visit Longboat Key, Florida, generally fall within the high season, which spans from December to April. This period coincides with the pleasant winter climate and attracts many visitors seeking warm weather and various outdoor activities. It's advisable to plan your trip and make reservations ahead of time during these months, as they are popular for vacationers looking to enjoy the island's beautiful beaches and attractions.

  • December: 73°F (23°C)
  • January: 70°F (21°C)
  • February: 72°F (22°C)
  • March: 76°F (24°C)
  • April: 80°F (27°C)

Longboat Key Low Season - May to November

The low season to visit Longboat Key, Florida, generally falls within the months of May through November. During this period, temperatures can be hotter and more humid, and there's a higher likelihood of rainfall, especially in the summer months.

The summer months are more popular with visitors closer geographically to Longboat Key like Florida residents, Georgia, South Carolina. These visitors are looking to escape the heat of their mainland locations.

While the low season might not be as popular as the high season due to the weather conditions, it can offer more budget-friendly travel options and a quieter atmosphere. Keep in mind that some amenities or businesses might have different operating hours or limited availability during the low season.

Longboat Key Monthly Stays - Snowbird Rentals

Longboat Key, Florida, is an ideal destination for snowbird monthly visitors due to its numerous appealing features and minimum 30 day rental restrictions for the majority of homes on the island. The mild and pleasant winter climate provides a welcome escape from colder northern regions. The temperatures during the high season, from December to April, are comfortable for outdoor activities without the extreme heat of summer. The island's pristine beaches, clear waters, and lush landscapes offer a beautiful setting for relaxation and exploration.

Furthermore, Longboat Key offers a wide range of amenities and activities that cater to the needs and interests of snowbird visitors. From golfing and water sports to cultural attractions and dining options, there's no shortage of things to do. The community's welcoming atmosphere and diverse social events create opportunities to connect with fellow snowbirds and locals alike.

With its upscale accommodations, vibrant cultural scene, and proximity to nearby Sarasota, Longboat Key offers a balanced blend of relaxation and engagement, making it an attractive choice for snowbird visitors seeking a fulfilling and enjoyable extended stay.

Choosing the long term suitability filter renders 33 Longboat Key monthly rentals for snowbirds.

Longboat Key Pet Friendly Rentals

Longboat Key, Florida, offers opportunities for dog owners to enjoy time with their furry friends. While the options may vary, here are a couple of dog-friendly parks and activities you can explore:

1. Joan M. Durante Park: This park on Longboat Key features nature trails and walking paths that you and your dog can enjoy together. It's a serene and beautiful environment for leisurely walks surrounded by natural beauty.

2. Coquina Beach walking path: While not on Longboat Key itself, Coquina Beach on nearby Anna Maria Island does have a dog-friendly area. Dogs are allowed on a designated stretch of the path which stretches over 2 miles.

3. Leashed Walks: While there might not be dedicated dog parks on Longboat Key, you can still take your dog for leashed walks along the sidewalks and paths around the island. Exploring the neighborhood together can be a delightful experience.

It's recommended to check the latest regulations and guidelines for dog-friendly areas, as rules can change. Additionally, if you're interested in specific dog-friendly activities or locations, you might want to reach out to local pet-friendly resources or forums to get the most current information.

Choosing the appropriate filter renders 1 Longboat Key pet friendly rentals on FLARBO.

Vacation Rental Statistics about Longboat Key Florida

Use the search filters on Florida Rental By Owners website to look for accommodations meeting your criteria.

Longboat Key Rentals with Pool and Hot Tubs

During your vacation, you'll find yourself spending ample time outdoors. The array of pool and hot tub options enhances the appeal of this destination, making it perfect for year-round enjoyment.

Longboat Key Rental Popular Searches

There is a great selection of Longboat Key vacation rental dwelling types, the majority ranging from condos to private homes: 

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