Longboat Key Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Longboat Key
Discover more than 813 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 864.6 ft², with nightly prices averaging US $404.
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.
Top Accommodation Types in Longboat Key
| Type | Count |
|---|---|
| Vacation Homes | 122 |
| Holiday Apartments | 75 |
| Villas | 6 |
| Cottages | 3 |
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.
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.
Other Places to Stay in Longboat Key, FL
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:
- End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,
- Stunning -late summer sale 50 ft from sand, Private Island 125 +review
- Island Time: Discounted August & September!
- THE BEACH CONDO #107 BEACHFRONT FULL VIEW
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
- Unit #210 Sand Cay Beach Resort Pool View
- Beachcomber unit 204
- Longboat Key Waterfront 3BR house w/Pool in most desirable Country Club Shores
- UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
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.
- Beachcomber unit 408
- LaPlaya 205D Spectacular sunsets and sunbathing from your private Gulf front lanai or sundeck
- Breathtaking Gulf Views Prestigious Long Boat Key
- Condo- steps to the sand
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:
- Longboat Key near St Armands Beachside Sanctuary 2BR/2BA w/Full Kitchen
- Top Floor Sunset Paradise Gulf View Unit 501
- Zota Beach Resort
How many Casai.com holiday rentals are available in Longboat Key?
As of 2026, Casai boasts over 813 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 | 2373 |
| Bay Isles Vacation Rentals in Sarasota, Florida | 819 |
