Discover a selection of 361 vacation rentals in Longboat Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $105 per night, and houses and condos are popular options for a stay in Longboat Key. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Longboat Key
Destination guide

Experience Longboat Key at vacation home rentals

Vacation treasures are just waiting to be unwrapped on this beach-lined ribbon of land in the Gulf of Mexico west of Bradenton and Sarasota. Known as a great location to pull out your fishing pole, Longboat Key also offers elegant resorts and upscale dining, plus opportunities to see nature up close and personal. It's only 30 minutes away from Bradenton-Sarasota airport, and just as easy to reach the cultural and family-friendly attractions in both communities. A Longboat Key vacation rental is a relaxing place to warm your heart on a midwinter getaway.

Things to do

Tourist attractions near Longboat Key vacation homes

A Longboat Key vacation rental is a convenient launching place to visit attractions around the area. Mote Marine Aquarium, just over the bridge to the south, has an open-water Shark Zone and exhibits on alligators, sting rays, manatees, sea turtles, and other aquatic life. South Florida Museum in Bradenton features a manatee aquarium and planetarium, plus exhibits on natural and cultural history. In Sarasota, visit the vast collection of the Ringling Museum of Art, plus the Marietta Museum of Art & Whimsy. Sarasota also offers botanical gardens and encounters of the retail kind.


Activities near your Longboat Key summer rental

If you're looking for sport fishing, Longboat Key is the place. Tarpon and cobia can be caught from the beach, and some docks are lighted for nighttime fishing. Redfish and speckled trout lurk in the mangroves. You can book a charter for offshore fishing—or a cruise just to view the dolphins. Gulf-side beaches beg you to loll in the sun, swim, take up windsurfing or parasailing, and rent paddle boards and boogie boards. There's a public tennis center. Beer Can Island is a boat-in stretch of beach for picnicking at the key's northern tip.


Climate for your trip to Longboat Key vacation rentals

Sunshine rules for 256 days a year on Longboat Key, making outdoor activities enjoyable all year from a Longboat Key vacation rental. Summer is the hottest season, and often humid, with July highs around 90. It's also the wettest, with August rainfall around 9 inches. January high temperatures are generally in the 80s, with the average low around 50. May to late fall is actually the slower season, with lower prices. The cooler, busier winter season is when visitors seek escape from cold and snow elsewhere. Spring and fall are in-between, for both weather and crowds.

Natural features

Good things in a small package on Longboat Key

Longboat Key occupies a narrow barrier island between the Gulf of Mexico and Sarasota Bay. Everything is packed into 4 square miles of dry land, and you could bike the 10 miles from northerly Beer Can Island to Quick Point in about 50 minutes. Sea turtles and shorebirds nest along the Gulf beaches from April to November, but habitats are protected by keeping observers at a distance and outdoor lights off at night. Crabs and conchs, egrets, herons, and osprey are seen from trails and boardwalks through 34 acres of wetland and mangrove lagoons at Quick Point Nature Preserve.


Best beaches near Longboat Key vacation homes

Longboat Key boasts gorgeous beaches ideal for swimming, sunbathing, and watersports. Vacation homes are available near places like Siesta Beach, a sandy beach with seaside amenities, and Anna Maria Public Beach, a white-sand beach with gentle surf for swimming. You'll also like Coquina Beach, a tranquil beach with turquoise waters and spectacular sunset views.

How to get there

How to get to and around Longboat Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 6.7 mi (10.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Good for couples

Romantic vacation rentals in Longboat Key

If you're looking for a romantic retreat, Longboat Key has an array of tranquil locations to explore. Vacation rentals are available near places like St. Armands Key, a bay island with serene tropical surrounds and parklands, and Leffis Key, an island nature reserve and tidal habitat with nature trails and boardwalks through the marshland. You could also visit Palma Sola Botanical Park, a landscaped garden with exotic plants and lakes.

What are the top vacation rentals in or near Longboat Key?

Luxury villas, quirky treehouses and cozy cottages — everyone's dream getaway is different. Whatever you're into, you're sure to find something you love among these top vacation rentals in Longboat Key:

  • "Rare 5th Floor Penthouse Take A Peek 100 + 5 Star Reviews": This Petrokefalo rental offers 1 bedroom and is rated highly among visitors. Conveniences such as high-speed internet services and a nearby beach will help you feel right at home.
  • "Luxury Upgraded Beachfront Condo With Breathtaking Views": Put your bags down and your feet up at this top pick in The South. It features 2 bedrooms, a fireplace, off-street parking options and more.

For even more great options, use the search bar at the top of the page to find the perfect Longboat Key vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Longboat Key?

Those chores can wait, because weekends were made for having fun. Get cozy at one of these weekend getaways in and near Longboat Key and experience all the exciting things to do nearby:

  • "Seaside Sanctuary - 1 Minute Walk From Front Door To Toes In The Sand" is a top-rated option around 12 miles northwest of central Longboat Key. You won't have to venture far to find something cool to do around this retreat. Get out and visit Anna Maria Sound and Pinellas Trail. Activities like cycling and fishing will nicely cap off your weekend away.
  • "Ami North End Ground Level Close To Beach Heated Saltwater Pool" is another dream escape to consider. Around 12 miles northwest of Longboat Key, use it as a base to do a little basketball or surfing and boogie boarding. Legacy Golf Club and The Bishop Museum of Science and Nature also have to be on your itinerary if you stay here.

Can I find studio apartments for rent in and around Longboat Key?

Typically small, easy on the wallet and well located, it's hard not to fall for the appeal of a studio apartment. Get cozy in one of these options and experience the energy of Longboat Key up close:

  • Explore the world around you from "Best Little Beach House On Anna Maria Island. . . With A Pool". This property is a fantastic base for discovering the sights and comes with amenities including internet services and games.
  • "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot" is another awesome option. Make yourself comfy and take advantage of internet services, a free nearby fitness center and more.

There are lots of sights around Longboat Key to add to your agenda. Satisfy the culture buff in you and visit Island Players and Madira Bickel Mound State Archaeological Site.

Can I find short term rentals in or near Longboat Key?

Yes, you certainly can! Vrbo's short-term rentals in Longboat Key are an excellent alternative to your typical cookie-cutter hotel room. Offering many of the conveniences of home, you'll easily be able to slip right into vacation mode the minute you arrive. Try one of these fantastic rentals on for size:

  • Stay a few nights at "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot" in central Longboat Key. Here, you'll enjoy easy access to attractions such as Premier Sports Campus at Lakewood Ranch.
  • "Aqua Beach - Luxury Villa Very Close To Beach With Private Pool" is another awesome option that welcomes short-term guests. Get the most out of your quick visit by stopping off at local sights, including TreeUmph! Adventure Course.

What are the best romantic weekend getaways in or near Longboat Key?

Forget flowers and chocolates. Sometimes all you need is to get away for the weekend, just the two of you. At Vrbo, we've got romantic getaways in and around Longboat Key that would make Cupid swoon. Here are some we think you'll love:

  • Slip away on Friday afternoon for a couple of passion-filled evenings at "New Completely Renovated Beach Front With Heated Pool Gulf View #102". Approximately 7 miles from Longboat Key, this property comes with lots of nice touches, like a nearby bay and beauty services.
  • Alternatively, spend your mini break enjoying each other's company at "Best Little Beach House On Anna Maria Island. . . With A Pool", around 9 miles from Longboat Key. Beauty services and air conditioning will help set the mood.

Are there mansions for rent in or near Longboat Key?

Nothing screams "Best. Vacation. Ever." like staying in a mansion. Treat the family to an unforgettable getaway at one of these mansions for rent in and around Longboat Key:

  • Charm, elegance and oodles of character — "Cretan Mansion From The 1900 Century Lovingly Restored With Garden" has it all, and then some. Approximately 4 miles northeast of Longboat Key and offering a porch and a nearby beach, this lovely place is hard to beat.
  • Another top pick is "Garden Apartment With Its Own Terrace In A Historic Mansion". Approximately 15 miles to the northeast of Longboat Key, this luxe vacation rental is the crème-de-la-crème of style and character and comes with a firepit, a swimming pool and more.

What are the best large group vacation rentals in or near Longboat Key?

Big groups mean big-time fun. They also mean finding a place that'll comfortably fit your whole gang. Browse our large group vacation rentals in or around Longboat Key and get your favorite people together under the one roof:

  • A range of amenities including a water view and a swimming pool make "Blue Water Beach House: 5+ Bedroom" a top pick for groups. This sprawling retreat has 6 bedrooms and sleeps up to 12 people. From central Longboat Key, it's around 9 miles away to the northwest.
  • Nothing takes priority over hanging out with loved ones, and "Family Fun Close To Beach, Pool Slide Spa And Elevator" makes it easy to do that. Located around 8 miles to the northwest of Longboat Key, as many as 12 people can stay in this vacation rental which has 4 bedrooms. A garden and a swimming pool are among the numerous amenities on offer here.

What are the best houses for rent with a pool in or near Longboat Key?

Of all the conveniences a vacation rental can offer, a pool is without a doubt the most fun. Have a look at these houses for rent with a pool in or near Longboat Key and spend your days splashing around. Just remember to bring your unicorn floatie:

  • Pack your swimsuit and make a booking at "Best Little Beach House On Anna Maria Island. . . With A Pool". There are also lots of other convenient amenities here, including outdoor furniture and a toaster.
  • Spend lazy vacation days splashing around or finding some peaceful moments beside the water at "Snead Island Tree House' Waterfront Apartment On 2 Acre Lot". This vacation rental is another top pick and features a separate dining area, a dining table and more.

Unsure how to pack your bags for your Longboat Key break? This popular destination has a humid subtropical climate. During summer, you can expect average temperatures ranging from 80 ºF to 90 ºF. Browse our selection of Longboat Key vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Longboat Key?

Every get-together with the family should be a memorable one. Whether you're planning a getaway with the kids or that long-overdue family reunion, our large family vacation rentals in or near Longboat Key offer a home away from home with ample space for everyone:

  • Get everyone under the same roof at "Ami North End Ground Level Close To Beach Heated Saltwater Pool", which has 3 bedrooms sleeping up to 8 guests. This retreat is located 12 miles to the northwest of Longboat Key and comes with amenities such as free toiletries and childrens activities.
  • Another top choice is "Blue Sky: Luxury 5 Bedroom/4 Bath With Heated Pool". This large rental is 11 miles northwest of Longboat Key and comes with a swimming pool, a TV and more. With 5 bedrooms accommodating up to 10 people, there's no need to leave anyone off your invitation list.

If you want to see some family-friendly attractions in the area, you have plenty of choice. TreeUmph! Adventure Course, Main Street at Lakewood Ranch and Historic Bridge Street Pier promise lots of fun for all the crew.

Can I find family cabin rentals in or near Longboat Key?

Time spent with family is priceless, which is why we'll help you find a place where you can truly connect. Book one of these family cabin rentals in or near Longboat Key and hang out with the people you love the most:

  • "Secluded Nautical Theme Cozy Cabin Awaits You" - This popular retreat offers coffee and tea making facilities and cable/satellite TV services and is located around 16 miles to the north of central Longboat Key.
  • "Convenient Cottage With Pool - Easy Access To Trolley Stops And The Beach" - Another excellent choice, this property comes with a swimming pool, a TV and more. You'll find it around 11 miles to the northwest of Longboat Key.

For more options, use the search bar at the top of the page and adjust the filters to find the Longboat Key vacation rental that's perfect for your needs.