744+ Private Villas and Holiday Rentals in Longboat Key |
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  3. Sarasota
  4. Longboat Key

Longboat Key Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Longboat Key

Discover more than 744 vacation rentals available in Longboat Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Longboat Key.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Longboat Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Longboat Key. On average, places to stay near Longboat Key offer 871.48 ft², with nightly prices averaging CA $514.

With Casai, finding and comparing holiday rentals in Longboat Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Longboat Key

Type Count
Vacation Homes 108
Holiday Apartments 67
Villas 8
Cottages 2

Use these Quick Filters to Find a Holiday Rental in Longboat Key

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Longboat Key.

Weather in Longboat Key, FL

View the weather forecast for Longboat Key before booking your Longboat Key Vacation Rentals to confirm your best time to go.

December - February
High 75°F       Low 58°F
March - May
High 86°F       Low 61°F
June - August
High 91°F       Low 76°F
September - November
High 89°F       Low 63°F

Top Attractions Around Longboat Key, FL

Casai offers a large selection of top attractions around Longboat Key . Research things to do on your vacation before you visit Longboat Key.


Longboat Key Beaches
Beer Can Island
Cannons Marina
Islandside Golf Course at Longboat Key Club
Quick Point Nature Reserve
Harborside Golf Course at Longboat Key Club
Jewfish Key
Lido Beach
Venice Beach
Siesta Key Beach
St. Armands Circle
Turtle Beach
IMG Academy
Fort De Soto Park
Nokomis Beach
Coquina Beach
Eckerd College
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital

Other Places to Stay in Longboat Key, FL


Jewfish Key 2,891 Properties
Beer Can Island 2,888 Properties
Longbeach Village 1,616 Properties
Quick Point Nature Reserve 1,244 Properties
Cannons Marina 1,090 Properties
Harborside Golf Course at Longboat Key Club 1,045 Properties
Islandside Golf Course at Longboat Key Club 1,041 Properties
Bay Isles 653 Properties
Longboat Key Beaches 416 Properties

Frequently Asked Questions About Longboat Key?

What are the top holiday rentals in Longboat Key?

With numerous options available in Longboat Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Longboat Key:

How many holiday rentals have private pools in Longboat Key?

Discover a selection of holiday rentals with private pools near Longboat Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Longboat Key are best for families?

If you're searching for a family-friendly holiday home in Longboat Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Longboat Key:

How many Casai.ca holiday rentals are available in Longboat Key?

As of 2025, Casai boasts over 744 properties listed in the Longboat Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Longboat Key.

Nearby Neighborhood (2) 
Neighborhood Property Count
Longbeach Village Vacation Rentals in Sarasota, Florida 1616
Bay Isles Vacation Rentals in Sarasota, Florida 653

People Also Ask

There are 744 Longboat Key, FL Holiday Rentals

Recently Booked Holiday Rentals in Longboat Key