As 20-year residents and the top Michael Saunder's & Company luxury realtor of Longboat key, we know what it's like to want a little paradise.

Steve and Janet Walter - Walter Group Real Estate - Sunset on the beach on Longboat Key Florida

But the idea of finding the perfect location and buying a vacation home can seem like an unattainable dream. However, with the correct information, resources, and a good realtor, owning a vacation home on Longboat Key is within reach for many buyers.

Longboat Key Aerial Photo Longboat Key Club Resort South End

We created this guide to give you insight into everything a prospective buyer would like to know about purchasing their dream vacation property in this exclusive island paradise.


Longboat Key, Florida, is one of the most popular vacation hotspots in the United States. The average monthly temperatures are from the mid-80s in winter and spring to the high-90s in summer. From its white sandy beaches and beachfront property to world-class local shops and dining opportunities, there is no shortage of things to do here.

St Armands Shopping District

Unsurprisingly, many people are interested in purchasing a rental property on the Key as an investment or even for their use as a second home.

Bay Isles Community Longboat Key Florida

When considering buying a vacation home, it is essential to understand the unique benefits such an acquisition can offer. Owning your piece of paradise has many advantages, including potential tax breaks and income from renting out your property during peak season when demand is high. You will also have access to stunning beaches year-round and plenty of other activities like golfing, fishing, and boating.

Contender on the Sarasota Bay with light chop anchored

Walter Group Real Estate - Michael Saunders & Co. Top Longboat Key Realtors

Walter Group Real Estate - Michael Saunders & Co. Top Longboat Key Realtors

Our mission is to help you achieve your Sarasota Islands' Real Estate Goals. Our brand promise is to engage our clients with intelligence, candor and goodwill in every transaction. Let us know how we can help.

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Factors To Consider Before Buying A Vacation Home On Longboat Key

When considering the purchase of a vacation home, some may think it's too risky or costly an endeavor. However, with careful research and planning, you can find that buying on the Key is an intelligent investment decision. Before making this significant commitment, there are certain factors to consider.

The Longboat Key population has grown significantly and continues attracting more visitors yearly. This hot market means looking into rental potential is essential, as many Longboat Key residents rent their properties when not using them. With its proximity to Sarasota International Airport, transportation should also be considered if you often visit without bringing your vehicle. If you fly into Tampa international airport, you are a 60-minute drive to Sarasota.

Sarasota Bradenton International Airport


Determine your budget for purchasing a vacation home, including property taxes, insurance, and maintenance costs. Remember that homes on Longboat Key can be more expensive due to their prime location.


Choose a location that meets your preferences for beach access, proximity to amenities, and neighborhood atmosphere.

L'Ambiance Condos

Consider whether you want a waterfront property, a home within a gated community, or a property with access to a marina or golf course. Some of the most sought-after communities are these:

  • Longboat Key Club

  • Lighthouse Point

  • Country Club Shores

  • Bay Isles

  • Sleepy Lagoon/Bayview Estates

  • Longboat Village

Rental potential

If you plan to rent your vacation home when you're not using it, research the local rental market to understand the potential income and demand. Factor in rental management fees, insurance, and maintenance costs.

Property type

Decide what type of property best suits your needs, whether a single-family home, condo, or townhouse. Each property type comes with its own advantages and responsibilities, so consider the level of maintenance you're willing to take on.

Zoning and building restrictions

Familiarize yourself with local zoning laws and building restrictions that could impact your ability to renovate or expand your vacation home. These regulations may also affect your property's rental potential.

Property management

Consider whether you'll manage the property yourself or hire a property management company. If you live far away or plan to rent the property, a professional property manager can help ensure everything runs smoothly in your absence.

Taxes and insurance

Research the local property tax rates and insurance requirements for vacation homes in Longboat Key. Coastal properties may have higher insurance premiums due to the risk of hurricanes and flooding.

Finally, having a highly qualified realtor to help understand the area before committing to buy will help ensure that the Key is the right fit for you and your family’s needs. Walter Group Real Estate is Michael Saunders & Company's premiere Longboat Key realtor group. We provide one-of-a-kind conceive real estate service to our many happy clients.

Walter Group Real Estate - Steve and Janet Walter - Serving Longboat Key for over 40 years

Types Of Vacation Homes on Longboat Key

Longboat Key offers a variety of vacation homes for buyers looking to invest in the perfect property. Homes on Longboat Key vary depending you want beachfront properties on the north end of the Island to luxury condos along the shores of Sarasota Bay.

Longboat Village Longboat Key Northend

Longboat Key boasts beauty and tranquility, making it an ideal location for buying a vacation home. Whether someone is seeking sun-drenched days at the beach or stunning views from their private balcony, something is available to suit every taste.

L'Ambiance balcony view of a sunset over the Gulf of Mexico

Beachfront homes

These homes are on the beach and offer stunning views of the Gulf of Mexico. They are ideal for those who want to spend their vacation lounging on the sand, swimming, and enjoying water sports.

3475 Gulf of Mexico Drive Longboat Key Florida Luxury Home on the beach Gulfside

Many luxury condominiums dot the gulf coast side providing its residents with a little more privacy with some of the most unobstructed amazing panoramic views of the island.

Beachplace Condos Longboat Key Florida

Waterfront homes

These homes are located on canals, bays, or lagoons and offer direct access to the water. They are ideal for those who want their own dock and access to Sarasota Bay. Country Club Shores Bay Isles and Sleepy Lagoon/Bayview Estates have some of the most sought-after single-family homes with deep water canals on Longboat Key.

Country Club Shores Longboat Key Florida - Deepwater Canals Private Boat Dock

Golf Course homes

The Resort at Longboat Key Club hosts two of the best golf courses on the west coast of Florida, Links on Longboat and The Harbourside Course. The Links on Longboat is located on the gulf side of Longboat and is lined with some of the most exclusive condos on the key.

The Resort at Longboat Key Club Harbourside Course Bay Isles Moorings Aerial view-

The Harbourside course resides in Bay Isles on the Sarasota Bay side of the island. Bay Isles is a gated community that offers luxury homes and condominiums with a private deep-water marina. The Moorings.

2027 Harbour Links Drive Longboat Key Florida overlooking the Harbourside Course at the Resort at the Longboat Key Club

Luxury homes

Longboat key offers its residents quiet, peaceful, and secure neighborhoods close to many amenities you would expect with luxury communities.

15 Lighthouse Point Dr. Longboat Key Florida - Luxury living


Condos are perfect for buyers that do not want to stay up with the ongoing maintenance that a home requires. Longboat Key provides some premium and luxurious condominium communities on the coast. Many condominiums are behind a private, gated entry and private beach access. Our top 10 most desirable condominiums with the best amenities are:

  1. Positano - A low-density condominium with a prioritization of green space providing first-class amenities with 29 units.

Positano condominiums Longboat Key Florida

  1. en Provence - 21-unit waterfront condominium built in 2001 with floor sizes between 3,400 and 6000 square feet.

en Provence Condos on Longboat Key Florida

  1. L'Ambiance - Resides inside the gated Longboat Key Club with ultra-luxury amenities, including 24-hour concierge service.

L'Ambiance condominiums

4. Vizcaya, 5. Water Club, 6. Sanctuary, 7. Promenade, 8. Villa Di Lancia, 9. Islander Club of Longboat and 10. Pierre.

L'Ambiance living room sunset on the Gulf of Mexico

The area also has plenty of amenities to offer its residents, such as nearby golf courses and tennis courts. Several shopping centers and art galleries are located throughout Longboat Key, making it easy for visitors to find whatever they need during their stay.

Additionally, those who purchase a vacation home here can take advantage of being close to downtown Sarasota with all its attractions and cultural offerings.

Viewing Downtown Sarasota Sunrise from Bayfront Park

Longboat Key Real Estate Market Overview

Longboat Key is a small community on the Gulf Coast of Florida. It has become an attractive destination for vacationers and retirees due to its white sand beaches, turquoise waters, excellent climate during the winter months, and close access to many island amenities minutes away from downtown Sarasota.

Lighthouse Point and and New Pass Longboat Key Florida

The real estate market offers a variety of properties, from single-family homes to waterfront condominiums, beachfront villas, and more. The current average listing price is around $1 million, with some exclusive properties commanding much more.

Positano Penthouse Longboat Key $5.295mm

The local market reflects the popularity of buyers looking for luxury living opportunities. Homes listed range from classic island cottages to modern high-end residences.

The Buying Process For Vacation Homes On Longboat Key

Buying vacation homes on Longboat Key can be very rewarding and exciting. With its sparkling waters and beautiful beaches, the island attracts home buyers worldwide.

Beer Can Island Beach Longboat Key Florida

However, due to its location in southwest Florida near Sarasota, this paradise has a higher price tag than other areas in the state. The key advice for any potential buyer is to research as much about the area as possible before committing.

Walter Group Real Estate | Your Trusted Longboat Key Realtor

It's beneficial to work closely with experienced real estate professionals with existing relationships in the community and understand what needs to be considered when purchasing property on the island, such as flood zones, deed restrictions, county codes, etc.

Longboat Key Vacation Home Waterfront Property Considerations

When considering the purchase of a vacation home on the Island, waterfront property can be an attractive option. With its miles of beaches and beautiful bays, this coastal Florida city has some of the most stunning views in the region. For potential buyers looking for that perfect place to relax and unwind, there are numerous considerations when selecting a waterfront property.

Country Club Shores, Longboat Key Florida

One example is the property's location relative to other amenities such as restaurants, world class shopping areas, and entertainment venues. Buyers should assess how close they want their vacation home to these attractions before purchasing. They may also want to consider whether or not they need access to boat ramps or docks if they plan to spend time on the water.

The Moorings Mariana at The Resort on Longboat Key

Longboat Key Vacation Home Rental Property Management

Property management is important to owning a vacation home. It involves the daily operation and maintenance of the property and ensuring that rental income is collected promptly. Hiring a professional property manager can benefit those looking to maximize their returns from renting out their vacation home.


Longboat Key, located in Florida, is ideal for individuals looking to purchase a vacation home. With its population growth and airport located nearby, the area has become increasingly popular due to the quiet atmosphere it offers visitors away from the hustle and bustle of many other destinations.

Further, those who visit Longboat Key are captivated by its romantic atmosphere and laid-back lifestyle that allows them to enjoy all of Florida’s west coast—offering exquisite cuisine to some of the most popular restaurants with a good mix of residents and vacationers. The Island offers some of the best real estate on Florida's Gulf coast.

Cafe L'Europe Restaurant St Armands Circle

Frequently Asked Questions

What Are The Property Tax Rates On Longboat Key?

Property taxes are an essential factor in purchasing a vacation home. Longboat Key is no exception, as property tax rates vary from region to region and even within the same county – Sarasota County. A good realtor who understands the property tax implications of buying on the Island can help inform your decision-making process.

What Is The Average Rental Rate For Vacation Homes On Longboat Key?

The local municipality sets specific regulations for renting property and vacation homes, which all owners must follow. Doing so allows them to maximize their profits while ensuring visitors have an enjoyable experience without any unexpected surprises. You can learn more about what the town of Longboat Key is changing for rental property here.

Are Any HOA Fees Associated With Owning A Vacation Home On Longboat Key?

When considering purchasing a vacation home on Longboat Key, you need a good real estate agent to familiarize yourself with the local area regulations and restrictions, which often dictate how much residents pay in HOA fees. Additionally, research should be conducted regarding any upcoming projects proposed within the community that could potentially increase existing fees or introduce new ones altogether.

Are There Any Restrictions On Short-Term Rentals On Longboat Key?

In certain areas of Longboat Key, regulations have been put in place limiting the number of nights a property can be rented out per year or restricting AirBnB-type activities altogether due to noise complaints or other issues associated with short-term renters. To help navigate the short-term restrictions, please consult with an experienced real estate agent.

Are There Any Restrictions On The Type Of Vacation Home That Can Be Built On Longboat Key?

Longboat Key is a popular destination for vacation homeowners who seek to capitalize on its stunning beaches, golf courses, and parks. Those considering investing in property there must be aware of the restrictions that may apply. Those related to the type of vacation homes permitted on the island are particularly important.

The Island has specific regulations regarding construction on residential properties. For example, all structures must meet local building codes and be approved by the county before being built.

Walter Group Real Estate

As luxury realtors with 20 years of experience serving Longboat Key and its surrounding areas, Steve and Janet of the Walter Group Real Estate specialize in representing buyers and sellers. We are committed to guiding you through the latest luxury listings and helping you find your dream home in paradise. Start your search with us today, and let us assist you in achieving your dream of owning a luxurious property in one of Florida's most beautiful coastal communities. Phone: (941) 809-0907

Walter Group Real Estate | Your Trusted Longboat Key Realtor

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