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Holiday homes in Longboat Key You’ll Love

Top-Rated Longboat Key Holiday homes for Every Budget and Style!

Looking for a holiday home in Longboat Key (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Longboat Key.

We found 445 Holiday-homes in Longboat Key and the surrounding area (within 20 miles)

Sunny Gulf Coast Villa Direct Beach and Pool Access in Longboat Key, USA

Sunny Gulf Coast Villa Direct Beach and...

Villa in Longboat Key, Florida
Sunny Gulf Coast Villa Direct Beach and Pool Access offers accommodations in Longboat Key, a few steps from Longboat Key Beach and 12 miles from The J...
  • Parking
  • Spa and wellness centre
  • Swimming pool
  • Swimming Pool

Fabulous 5 Reviews 9.0

from $328.04 Show details »

Shorewalk 2 Bedroom 2 Bathroom Near IMG And Bradenton Beach in Bradenton, USA

Shorewalk 2 Bedroom 2 Bathroom Near IMG...

Villa in Bradenton near Longboat Key, Florida , 4535 46th st ct west unit 104
8.5 miles from The John and Mable Ringling Museum of Art in Bradenton, Shorewalk 2 Bedroom 2 Bathroom Near IMG And Bradenton Beach provides accommodat...
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming pool

Very good 36 Reviews 8.1

from $155.07 Show details »

Captain’s Quarters at Anna Maria Island Inn in Bradenton Beach, USA

Captain’s Quarters at Anna Maria Island...

Villa in Bradenton Beach near Longboat Key, Florida , 110-112 8th St
Captain’s Quarters at Anna Maria Island Inn offers accommodations in Bradenton Beach, 14 miles from The John and Mable Ringling Museum of Art and 6....
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 133 Reviews 8.8

from $187.43 Show details »

Gulf Coast Retreat in Bradenton, USA

Gulf Coast Retreat

Villa in Bradenton near Longboat Key, Florida
Gulf Coast Retreat offers accommodations in Bradenton, 8.1 miles from The John and Mable Ringling Museum of Art and 29 miles from Tropicana Field.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $134.33 Show details »

NEW Dog Paradise - Near the Beach IMG & Downtown in Bradenton, USA

NEW Dog Paradise - Near the Beach IMG &...

Villa in Bradenton near Longboat Key, Florida , 3719 118th Street West
NEW Dog Paradise - Near the Beach IMG & Downtown offers accommodations in Bradenton, 13 miles from The John and Mable Ringling Museum of Art and 8 mil...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Exceptional 4 Reviews 10.0

from $69.00 Show details »

Villa Seaside Anchor in Bradenton Beach, USA

Villa Seaside Anchor

Villa in Bradenton Beach near Longboat Key, Florida , Avenue B
Villa Seaside Anchor is located in Bradenton Beach, just a 14-minute walk from Cortez Beach and 1.3 miles from Holmes Beach.
  • Swimming Pool

no reviews

from $58.00 Show details »

Villa Summer Retreat in Bradenton Beach, USA

Villa Summer Retreat

Villa in Bradenton Beach near Longboat Key, Florida , Avenue B
Villa Summer Retreat offers accommodations in Bradenton Beach, 15 miles from The John and Mable Ringling Museum of Art and 5 miles from Anna Maria Cit...
  • Parking

no reviews

from $96.00 Show details »

Anna Maria Oasis Resort Style Heated Pool Mini Golf EV Station in Bradenton, USA

Anna Maria Oasis Resort Style Heated Poo...

Villa in Bradenton near Longboat Key, Florida , 1227 De Narvaez Avenue
Anna Maria Oasis Resort Style Heated Pool Mini Golf EV Station is located in Bradenton, just a 17-minute walk from Palma Sola Causeway Park and 12 mil...
  • Parking
  • Restaurant
  • Fitness centre
  • Family rooms
  • Outdoor pool

Exceptional 3 Reviews 10.0

from $72.00 Show details »

Glorious Daze in Holmes Beach, USA

Glorious Daze

Villa in Holmes Beach near Longboat Key, Florida , 2912 Avenue East
Glorious Daze offers accommodations in Holmes Beach, 15 miles from The John and Mable Ringling Museum of Art and 4.1 miles from Anna Maria City Pier.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $59.00 Show details »

Full Kitchen - Shared Pool - By Loverentals in Holmes Beach, USA

Full Kitchen - Shared Pool - By Loverent...

Villa in Holmes Beach near Longboat Key, Florida , 2919 Avenue East #1
Full Kitchen - Shared Pool - By Loverentals is located in Holmes Beach, just 15 miles from The John and Mable Ringling Museum of Art and 4.1 miles fro...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $68.00 Show details »

Steps From Beach! Grill - Wifi - By Loverentals in Holmes Beach, USA

Steps From Beach! Grill - Wifi - By Love...

Villa in Holmes Beach near Longboat Key, Florida , 2919 Avenue East #3
Steps From Beach!
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $235.07 Show details »

Steps From Beach! Air-Conditioned - Shared Pool in Holmes Beach, USA

Steps From Beach! Air-Conditioned - Shar...

Villa in Holmes Beach near Longboat Key, Florida , 2919 Avenue East #2
Steps From Beach!
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $243.06 Show details »

The Surf Shack in Holmes Beach, USA

The Surf Shack

Villa in Holmes Beach near Longboat Key, Florida
The Surf Shack is located in Holmes Beach, just a 3-minute walk from Bradenton Beach and one mile from Anna Maria Island.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $448.30 Show details »

Las Hermanas 2 in Longboat Key, USA

Las Hermanas 2

Holiday home in Longboat Key, Florida , 2813 Gulf of Mexico Drive
Las Hermanas 2 is located in Longboat Key, just 11 miles from The John and Mable Ringling Museum of Art and 4 miles from Mote Marine Laboratory.

no reviews

from $630.43 Show details »

Las Hermanas 3 in Longboat Key, USA

Las Hermanas 3

Holiday home in Longboat Key, Florida , 2813 Gulf of Mexico Drive
Las Hermanas 3 offers accommodations in Longboat Key, 11 miles from The John and Mable Ringling Museum of Art and 4 miles from Mote Marine Laboratory.

Exceptional 4 Reviews 9.8

from $443.00 Show details »

Sunset Sanctuary in Longboat Key, USA

Sunset Sanctuary

Holiday home in Longboat Key, Florida , 540 Neptune Avenue
Sunset Sanctuary offers accommodations in Longboat Key, a 2-minute walk from Longboat Key Beach and 11 miles from The John and Mable Ringling Museum o...

no reviews

from $50.00 Show details »

Longboat Key Beach House Beauty With Peek-a-views in Longboat Key, USA

Longboat Key Beach House Beauty With Pee...

Holiday home in Longboat Key, Florida , 2932 Gulf of Mexico Drive
Longboat Key Beach House Beauty With Peek-a-views offers accommodations in Longboat Key, a few steps from Longboat Key Beach and 11 miles from The Joh...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $60.00 Show details »

Freesia at Seaside Gardens in Longboat Key, USA

Freesia at Seaside Gardens

Holiday home in Longboat Key, Florida
Freesia at Seaside Gardens offers accommodations in Longboat Key, a few steps from Longboat Key Beach and 11 miles from The John and Mable Ringling Mu...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $83.00 Show details »

Buttonwood Bliss in Longboat Key, USA

Buttonwood Bliss

Holiday home in Longboat Key, Florida , 3660 Gulf of Mexico Drive, Unit 102A
Buttonwood Bliss is located in Longboat Key, just 11 miles from Sarasota Jungle Gardens and 12 miles from Van Wezel Performing Arts Hall.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $88.00 Show details »

Casa Limon with HEATED POOL in Sarasota, USA

Casa Limon with HEATED POOL

Holiday home in Sarasota near Longboat Key, Florida , 484 Parkview Drive
Just a 14-minute walk from The John and Mable Ringling Museum of Art and 0.8 miles from Van Wezel Performing Arts Hall, Casa Limon with HEATED POOL fe...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $441.64 Show details »

Coastal Villa W Amazing Courtyard - Splash Pad! in Sarasota, USA

Coastal Villa W Amazing Courtyard - Spla...

Holiday home in Sarasota near Longboat Key, Florida , 8479 Pinewood Road
Coastal Villa W Amazing Courtyard - Splash Pad! enjoys a location in Sarasota, a 14-minute walk from The John and Mable Ringling Museum of Art and 0.7...
  • Parking

Good 17 Reviews 7.8

from $149.98 Show details »

Serenity on Sutton in Longboat Key, USA

Serenity on Sutton

Holiday home in Longboat Key, Florida , 540 Sutton Place
Serenity on Sutton offers accommodations in Longboat Key, 13 miles from The John and Mable Ringling Museum of Art and 6.2 miles from Mote Marine Labor...
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $99.00 Show details »

Coastal Sol in Sarasota, USA

Coastal Sol

Holiday home in Sarasota near Longboat Key, Florida , 7726 Westmoreland Dr
Coastal Sol offers accommodations in Sarasota, 2 miles from The John and Mable Ringling Museum of Art and 1.8 miles from Van Wezel Performing Arts Hal...
  • Parking
  • Pets allowed

Good 1 Reviews 7.0

from $307.00 Show details »

10 Pines - Sarasota Bay in Sarasota, USA

10 Pines - Sarasota Bay

Holiday home in Sarasota near Longboat Key, Florida
10 Pines - Sarasota Bay is located in Sarasota, just 2.4 miles from Van Wezel Performing Arts Hall and 3.6 miles from Sarasota Jungle Gardens.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 8 Reviews 9.1

from $382.73 Show details »

Pura Vida in Longboat Key, USA

Pura Vida

Holiday home in Longboat Key, Florida , 5310 Gulf of Mexico Drive
Pura Vida offers accommodations in Longboat Key, 14 miles from The John and Mable Ringling Museum of Art and 13 miles from Sarasota Jungle Gardens.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $489.41 Show details »

Number of Holiday homes in Longboat Key 445
Number of guest ratings 848
Average price per night $492.00
Lowest price per night $50,00
Highest price per night $7.021,17

Top 10 Cheapest Holiday-homes in Longboat Key

Discover the Cheapest Holiday-homes in Longboat Key – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Longboat Key

Check out the Most Booked Holiday-homes in Longboat Key – Based on Guest Popularity.

Holiday homes in Longboat Key (Florida), comfortable and familiar

Staying in a holiday or vacation home in Longboat Key can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Longboat Key for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Longboat Key should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com