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Longboat Key vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Longboat Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Longboat Key

4.87 out of 5 average rating, 104 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with 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, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Guest favorite

Apartment in Longboat Key

4.82 out of 5 average rating, 124 reviews

Ocean Front Studio Special From $99/night

This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.

Jul 8 – 15

€ 232 per night
Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 298 reviews

*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Jan 22 – 29

€ 625 per night

Popular amenities for Longboat Key vacation rentals

Stay near Longboat Key's top sights

IMG Academy36 locals recommend
Beer Can Island32 locals recommend
Dry Dock Waterfront Grill74 locals recommend
Mar Vista Dockside Restaurant88 locals recommend
IMG Academy Golf Club9 locals recommend
New Pass Grill & Bait Shop33 locals recommend

Longboat Key condo rentals

Guest favorite

Condo in Siesta Key

4.9 out of 5 average rating, 149 reviews

Cozy Siesta Key studio 5 minute walk to Village

Nov 12 – 19

€ 173 per night
Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 455 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Nov 9 – 16

€ 111 per night
Guest favorite

Condo in Bradenton Beach

4.9 out of 5 average rating, 123 reviews

Beachfront condo in paradise

Dec 6 – 13

€ 339 per night
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 268 reviews

On the Beach; Siesta Key SunBum Studio

Jan 1 – 8

€ 479 per night
Guest favorite

Condo in Treasure Island

4.99 out of 5 average rating, 150 reviews

Spectacular beach to bay views from this resort.

Sep 12 – 19

€ 215 per night
Guest favorite

Condo in Redington Beach

4.91 out of 5 average rating, 107 reviews

Royal Orleans and Redington Beach ( Studio 203 )

Dec 8 – 15

€ 108 per night
Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 167 reviews

Shorewalk full condo IMG Beaches Anna Maria

Aug 31 – Sep 7

€ 162 per night
Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 200 reviews

Sunset Beach Condo in Treasure Island

Sep 13 – 20

€ 145 per night
Guest favorite

Condo in Siesta Key

4.83 out of 5 average rating, 187 reviews

New: Cozy 1BR Beach Condo on Siesta Key!!!

Jul 26 – Aug 2

€ 195 per night
Guest favorite

Condo in Holmes Beach

4.99 out of 5 average rating, 121 reviews

Beach Escape - Make Memories on Anna Maria Island!

Oct 24 – 31

€ 301 per night
Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 142 reviews

1 BR direct beachfront! Now available May 22-27!

Oct 30 – Nov 6

€ 182 per night
Guest favorite

Condo in Holmes Beach

4.92 out of 5 average rating, 156 reviews

Anna Maria Beach Place...footsteps to the sands

Nov 26 – Dec 3

€ 264 per night

Longboat Key home rentals

Guest favorite

Home in Longboat Key

4.89 out of 5 average rating, 104 reviews

Longboat Key Beach House

May 20 – 27

€ 469 per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 127 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Jul 19 – 26

€ 145 per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 107 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Sep 10 – 17

€ 144 per night
Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 149 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Dec 5 – 12

€ 558 per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 124 reviews

Ranch 2 blocks from Sarasota Bay

Dec 15 – 22

€ 141 per night
Guest favorite

Home in Holmes Beach

4.96 out of 5 average rating, 157 reviews

Sea AMI

Oct 7 – 14

€ 319 per night
Guest favorite

Home in Sarasota

5.0 out of 5 average rating, 274 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Jul 17 – 24

€ 274 per night
Guest favorite

Home in Sarasota

4.85 out of 5 average rating, 162 reviews

Authentic Florida Bungalow near Downtown and Beach

Apr 29 – May 6

€ 117 per night
Guest favorite

Home in Sarasota

4.91 out of 5 average rating, 142 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

Nov 3 – 10

€ 117 per night
Guest favorite

Home in Siesta Key

5.0 out of 5 average rating, 122 reviews

One-of-a-kind*Beach, Village, Dock & Private Pool!

Nov 7 – 14

€ 626 per night
Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 150 reviews

Peaceful Braden River Oasis: Cottage

Aug 30 – Sep 6

€ 112 per night
Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

Oct 23 – 30

€ 555 per night

Longboat Key villa rentals

Guest favorite

Villa in Sarasota

4.89 out of 5 average rating, 181 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Sep 13 – 20

€ 253 per night
Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 130 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Jan 10 – 17

€ 318 per night
Guest favorite

Villa in Englewood

4.92 out of 5 average rating, 107 reviews

Magnificent Waterfront! Kayaks-Pool-Beach! gs

Sep 3 – 10

€ 177 per night
Guest favorite

Villa in Siesta Key

4.9 out of 5 average rating, 133 reviews

Mermaid Villa Ocean Front!

Sep 21 – 28

€ 843 per night
Guest favorite

Villa in Bradenton

4.83 out of 5 average rating, 133 reviews

Elegant private home 3Bdr/3bth

Jun 29 – Jul 6

€ 328 per night
Guest favorite

Villa in Tampa

4.91 out of 5 average rating, 166 reviews

Busch Gardens, Moffitt, USF Charming Villa

Apr 27 – May 4

€ 134 per night
Guest favorite

Villa in Redington Shores

4.9 out of 5 average rating, 106 reviews

Beachside 1 min to sand. Peaceful Walkable

Sep 9 – 16

€ 343 per night
Guest favorite

Villa in Sarasota

4.9 out of 5 average rating, 176 reviews

Hansen- Gorgeous 3BR/2BA Villa near Siesta Key

Jul 14 – 21

€ 346 per night
Guest favorite

Villa in Clearwater

4.91 out of 5 average rating, 210 reviews

V3- 1 BR, waterfront villa, 2 min walk 2 beach

Dec 14 – 21

€ 205 per night
Guest favorite

Villa in Safety Harbor

5.0 out of 5 average rating, 109 reviews

Villa Key West "Villas by Christine"

Jun 1 – 8

€ 213 per night
Superhost

Villa in St. Petersburg

4.84 out of 5 average rating, 106 reviews

St. Pete Beach Oceanfront Villa Saltwater Pool

Dec 3 – 10

€ 365 per night
Guest favorite

Villa in Sarasota

4.84 out of 5 average rating, 125 reviews

Cozy, pet-friendly Home 3 miles to Siesta Key #1

Nov 14 – 21

€ 236 per night

Quick stats about vacation rentals in Longboat Key

Total rentals

800 properties

Rentals with a pool

610 properties have a pool

Pet-friendly rentals

140 properties allow pets

Family-friendly rentals

580 properties are a good fit for families

Total number of reviews

8.3K reviews

Nightly prices starting at

€ 28 before taxes and fees

Your guide to Longboat Key

All About Longboat Key

Stretching between the Gulf of Mexico and Sarasota Bay, the barrier island of Longboat Key has attracted its share of sun-seekers, who can be found teeing off at the sweeping gulf-front golf courses or fishing in the mangroves for speckled trout. With Siesta Key to the south and Anna Maria Island to the north, Longboat Key has an upscale feel, with nice restaurants, luxury resorts, and 256 days of annual sunshine. At the northern tip is Beer Can Island, a popular picnic spot that’s prettier than its name might suggest; the untouched, white-sand beach is even accessible on foot at low tide. Paddleboarding, windsurfing, and other on-the-water activities beckon you into the Gulf. And when you’ve finally kicked the sand from your toes and are ready for some culture, you can visit the Ringling Museum of Art in Sarasota, which showcases the circus impresario’s vast collection of classic and modern European and American artworks.


The best time to stay in a vacation rental in Longboat Key

There’s a saying that the local visitors’ bureau likes to use: It’s always summer in Sarasota County. Longboat Key gets its best weather in the fall, winter, and spring, when temperatures stay in the 70s Fahrenheit and Gulf breezes keep things comfortable. These summer-like seasons are preferable to actual summers, which can be rainy and hot, with temperatures in the 90s, not to mention humid and buggy. No matter when you visit, bring your swimsuit: The water is swimmable all year round, and rarely drops below 68 degrees.


Top things to do in Longboat Key

St Armands Circle

This round little island shopping center just south of Longboat Key is home to high-end boutiques, art galleries, fine dining, and other urbane attractions. Surrounded by water on all sides, it makes for a perfect scenic day of shopping. Check the calendar for special events throughout the year.

Coquina Beach

Just a few minutes’ drive over the Longboat Pass Bridge, this relaxed white-sand beach at the southern end of Anna Maria Island is worth a visit for its scenic sunset views. Hunt for shells, play some beach volleyball, and keep an eye out for passing pods of dolphins.

Quick Point Nature Preserve

A short (0.8-mile) walking trail wends its way through 34 acres of protected wetlands and mangrove lagoons. If you’re lucky you might spot a dolphin swimming through the seagrass, or watch a heron, egret, or ibis hunting for its dinner.

Frequently Asked Questions

  • What types of vacation rentals are available in Longboat Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Longboat Key. From over 330 condo rentals, over 190 house rentals to over 10 villa rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Longboat Key?

    Yes! Work meets play with ease at over 280 vacation rentals in Longboat Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Longboat Key?

    Four-legged friends are welcome in Longboat Key. Choose from more than 140 vacation rentals for guests traveling with pets.

  • Are there Longboat Key condo rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 290 condo rentals with pools in Longboat Key, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in condo rentals in Longboat Key?

    Experience the best of Longboat Key with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly condo rentals in Longboat Key?

    Longboat Key has more than 250 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Longboat Key have a bbq area?

    Absolutely! We offer over 90 condo rentals with a bbq area in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have a gym?

    Absolutely! We offer over 80 condo rentals with a gym in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have self check-in?

    Absolutely! We offer over 50 condo rentals with self check-in in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Longboat Key have free parking?

    Absolutely! We offer over 320 condo rentals with free parking in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key