Longboat Key Vacation Rentals

(55 rentals)
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2 BR | 1.5 BA | Sleeps 4 | Quick View

1

$167

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Our canal front condo is avaialble for rent December 2024 - March 2025. Cedars East (0.6 mile walk) offers monthly memberships for tennis/pool/fitness center. The kitchen and bathrooms have been completely remodeled this year. Appliances, cabinets, sectional sofa with sleeper and Roku TV are all new. ...

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Property Type

Longboat Key Townhome

"Highly recommend!!"

We just spent 2 months at Tim’s condo and can’t speak highly enough about it! The location is perfect, mid island, walk to beach, on the canal which is just beautiful!! It’s great to have 2 floors ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$350

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to Longboat Key - you've stumbled on a unique hidden gem tucked away on the upper Gulf Coast of Florida. Small, private, and quiet - the key vacation that really makes you get away from it all. Our condominium in Bayport Beach and Tennis Club is a beautiful private retreat with unobstructed ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Discover a unique, remodeled 1920s bungalow near Whitney Beach and the bay, offering an open layout with high ceilings and modern appliances. This home features a heated pool, hot tub, and lush, private landscaping. Originally a post office, it has historical charm with a fully fenced yard, boat parking. ...

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Property Type

Longboat Key House

"Beautiful accommodations"

After my first great experience at the landlord’s other property, I booked this one. Again, the landlord was fabulous and met all our needs. The furnishings were beautiful and very clean. The beds are ...

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Longboat Key Harbour
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1 BR | 1 BA | Sleeps 4 | Quick View

4

$130

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is ...

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Property Type

Longboat Key Condo

"Excellent Stay"

We had such a great time in this condo. It was convenient to pool and beach. Also some great restaurants close by. We enjoyed the manatees from the pool. We look forward to returning. What a great ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 5 feet to Just outside your door & window

$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful!No need to fight any traffic or an overcrowded public beach. Beautiful view of the turquoise waters of the Gulf of Mexico. It is very private and peaceful. The ideal spot for a relaxing getaway ...

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Property Type

Longboat Key Condo

"Happy in Longboat Key"

We enjoyed our stay & owners were very helpful for helping us when needed! Beautiful view of the Gulf! Unit was sparkling clean & well equipped & comfortable. We are returning next year as well. The property ...

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Longboat Key Vacation Rentals

Longboat Key Weather

 | 

7222°  5111°
JANUARY
Ocean 6418°
7423°  5312°
FEBRUARY
Ocean 6518°
7725°  5714°
MARCH
Ocean 6719°
8228°  6016°
APRIL
Ocean 7323°
8731°  6518°
MAY
Ocean 7826°
9032°  7122°
JUNE
Ocean 8228°
9133°  7323°
JULY
Ocean 8530°
9133°  7323°
AUGUST
Ocean 8730°
9032°  7222°
SEPTEMBER
Ocean 8529°
8529°  6518°
OCTOBER
Ocean 8228°
8027°  5915°
NOVEMBER
Ocean 7524°
7423°  5312°
DECEMBER
Ocean 6921°

Escape to the Stunning Southwest Florida Shores with Longboat Key Condos for Rent


If you’re looking for some rest and relaxation after a tough few months at work or a long school year, Longboat Key vacation rentals are where it's at! As soon as your feet hit the sand and you feel the sun on your skin, the stress will begin to melt away.

Southwest Florida is home to so many unique and scenic beach towns. Some of them are small and sleepy, others are lively and energetic, and many more have an inviting mix of both. Are you unsure of where along the Florida coast to book your next vacation? As you deliberate, make sure to keep Longboat Key on your radar.

Longboat Key is a small, tight-knit community located on one of western Florida’s many barrier islands. To the east of Longboat Key is Sarasota Bay, and to the west is the expansive Gulf of Mexico. Thus, no matter where you are on Longboat Key, you’re sure to have a gorgeous view of the water and a short walk to the beach.

As you’re planning your beachside vacation in Longboat Key, you might be wondering whether to book a hotel for your lodging or choose something a bit more special. At FloridaRentals, we know firsthand how much more memorable staying in a rental home can make any vacation when compared to overbooked and noisy hotels.

When you book a Longboat Key rental for your trip, you’ll be able to rest easy knowing that your lodging is fully private and you’re guaranteed some much-needed peace and quiet. What’s more: our listings include homes of all sizes and locations, so finding the right rental home for you and your family is quick and easy.

Booking only takes a few minutes. After that, you’ll be one step closer to an incredible vacation in Longboat Key.

Best Restaurants Near Longboat Key Vacation Rentals


Love an ocean view when you’re dining? In Longboat Key, the closeness of the Gulf of Mexico and Sarasota Bay on either side means that nearly every restaurant in town has a view of the water.

Perhaps you’re looking for an upscale romantic establishment for date night or a casual spot for a quick lunch or dinner with family. No matter what sort of cuisine you desire, Longboat Key’s many eateries are sure to satisfy.

If you’re on a romantic getaway to Longboat Key with your significant other, you should consider making reservations at Euphemia Haye Restaurant. You’re guaranteed to have a memorable date night at this fine dining establishment.

Housed in one of the Key’s historic beachside cottages, the menu features a varied list of global dishes and plenty of fine wines. And once you’ve finished your dinner, you can head upstairs to The Haye Loft to enjoy a nightcap and a decadent dessert crafted by the incredible in-house chefs.

It wouldn’t be a proper trip to the Florida coast without some authentic and delicious seafood. The Lazy Lobster is the perfect spot to get just that, and it is only a few steps away from the shores of Sarasota Bay.

Each dish at The Lazy Lobster is crafted with only the freshest seafood and other locally sourced ingredients. Add in a varied list of unique cocktails and craft beers and you’ve got yourself a lively and delicious lunch or dinner.

If you’re ever in need of some coffee to fuel your long day of outdoor exploration, Turtle Coffee Bar is a local favorite for coffee and tea drinks of all kinds. Only adding to the magic is the fact that you can walk straight from the establishment to the beach in minutes by crossing Gulf of Mexico Drive.

Traveling to Longboat Key


If you’re flying into Florida to visit Longboat Key, the most convenient airport to use is Sarasota Bradenton International Airport. From there, it is recommended that you rent a car rather than use public transit so that you can visit the many destinations available and take your time along your route. A rental car also allows you to travel up and down Longboat Key with ease.

The drive from Sarasota Bradenton International Airport to Longboat Key is roughly 14 miles, which usually takes fewer than 30 minutes to complete. If you’re traveling into town from elsewhere in Florida, you’ll likely use routes like U.S. Highway 301 (north to south) and State Roads 72 or 70 (east to west) to reach Longboat Key.

Longboat Key Activities for Every Lifestyle


Though Longboat Key has a sleepy vibe perfect for slow-paced living and plenty of relaxation, there is no shortage of activities to explore. Whether you’re looking for an adventure or some calming pastimes to enjoy on your vacation, Longboat Key has it all.

For some fun in the sun, Bayfront Park is a popular destination. This public park is located right on the shore of Sarasota Bay, providing stunning ocean views as well as direct beach access.

Some other amenities that visitors can use at Bayfront Park include plenty of sports courts and open fields, a large play structure for kids, and picnic tables perfect for a casual lunch by the water.

Just south of Longboat Key on Lido Shores is the Mote Marine Laboratory & Aquarium. Here, visitors can learn all about the local marine life surrounding Longboat Key and beyond and gain a new appreciation for native wildlife. There are also plenty of hands-on exhibits and activities for kids and visitors of all ages to enjoy.

When you visit Longboat Key, you can explore many different beaches, all of which feature glistening white sand and warm turquoise waters. However, Little Beach is one of the town’s most popular lookouts and beaches. Protected by pieces of land, the waters at Little Beach are very calm and inviting for visitors of all ages.

Your perfect vacation in Longboat Key is waiting for you. Get started by perusing all of our rental homes on FloridaRentals today.


FAQ

How many vacation rentals are there in/around Longboat Key?

There are 55 Longboat Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Longboat Key?

There are vacation rentals available in Longboat Key for as low as $92 per night with an average price per night of $212.

Can I find a vacation rental in Longboat Key?

Yes, you can find vacation rentals in Longboat Key close to Coquina Beach, Durante Community Park, and Longboat Key. Don't forget to stop in to Quick Point Nature Reserve or Bayfront Park.

Do any vacation rentals in Longboat Key have a pool?

Yes, there are 9 vacation rentals with a pool in Longboat Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Longboat Key vacation rentals on the ocean?

There are 18 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!