Holiday rentals in Longboat Key

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Top-rated holiday rentals in Longboat Key

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

Guest favourite

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

₹42,685 per night
Guest favourite

Flat 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.

8–15 Jul

₹17,659 per night
Guest favourite

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!

22–29 Jan

₹48,999 per night

Popular amenities for Longboat Key holiday 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

Other great holiday rentals in Longboat Key

Guest favourite

Apartment in Longboat Key

4.8 out of 5 average rating, 56 reviews

On the water condo #4

16–23 Mar

₹9,204 per night
Guest favourite

Apartment in Longboat Key

4.79 out of 5 average rating, 14 reviews

Beer Can Beach Bungalow (weekly availability)

4–11 Jul

₹19,054 per night
Guest favourite

Apartment in Longboat Key

4.94 out of 5 average rating, 16 reviews

Turtle Shores Beachfront Oasis!

28 Sep – 5 Oct

₹31,131 per night
Guest favourite

Apartment in Longboat Key

4.96 out of 5 average rating, 50 reviews

Secluded Bayside Gem with beautiful bay views

18–25 Sep

₹21,670 per night
Guest favourite

Apartment in Longboat Key

4.95 out of 5 average rating, 19 reviews

Island property on Longboat Key by the Beach

14–21 Nov

₹25,431 per night
Guest favourite

Home in Longboat Key

5.0 out of 5 average rating, 45 reviews

Beautiful Beach House

24–31 Jan

₹30,517 per night
Guest favourite

Apartment in Longboat Key

4.95 out of 5 average rating, 44 reviews

Beachfront Condo- Quiet & Secluded Private Beach

19–26 Dec

₹55,632 per night
Guest favourite

Apartment in Longboat Key

4.86 out of 5 average rating, 80 reviews

Sunset and beach view from your balcony Unit 403

18–25 Sep

₹24,472 per night
Guest favourite

Townhouse in Longboat Key

4.81 out of 5 average rating, 27 reviews

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

30 Jul – 6 Aug

₹27,786 per night
Guest favourite

Apartment in Bradenton Beach

4.99 out of 5 average rating, 89 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

1–8 Sep

₹35,437 per night
Guest favourite

Apartment in Nokomis

5.0 out of 5 average rating, 13 reviews

Private Studio (entire space)

16–23 Aug

₹7,871 per night
Guest favourite

Home in Sarasota

4.89 out of 5 average rating, 38 reviews

Centrally Located Cozy Home

13–20 Sep

₹9,483 per night

Quick stats about holiday 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

8.3T reviews

Nightly prices starting at

₹2,500 before taxes and fees

Destinations to explore

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