6331+ Private Villas and Holiday Rentals in Siesta Key |
  1. USA
  2. Florida
  3. Sarasota
  4. Siesta Key

Siesta Key Holiday Rentals

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

Discover more than 6331 vacation rentals available in Siesta 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 Siesta Key.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Siesta 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 Siesta Key. On average, places to stay near Siesta Key offer 1026.25 ft², with nightly prices averaging $505.

With Casai, finding and comparing holiday rentals in Siesta 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.

Show more
Show less

Things to Know Before You Visit Siesta Key

Siesta Key, a barrier island on Floridas West Coast, is a beach lovers paradise. Whether youre visiting for a week or just an afternoon, there are plenty of ways to enjoy the sights and sounds of this lively community. In fact ,there are so many possibilities that it can feel overwhelming as soon as you arrive at the Siesta Key beach.

To make it easy for you, here are 6 great things you should do while visiting Siesta Key.

  1. Greet the morning with a stroll on the beach.
  2. Take a yoga class on the beach or try out one of the other intown studios from something unique, like aerial yoga.
  3. Walk or run around Siesta Key Village to grab breakfast at one of the many cafu00e9s, restaurants, and coffee shops.
  4. Take a stroll along the bayside path to unwind. Rent rollerblades, bikes, or kayaks if youd a different way to get around. If youre not feeling active, walk through Roberts Bay Hammock Park instead. Its a lush oasis that will make you feel like youre somewhere else.
  5. Go beachcombing for shells and sand dollars at Roberts Bay Nature Park .
  6. Stroll down to the public beach access on Stickney Point Road before or after your Siesta Key sunset, which you wont want to miss! Then head over to one of the many outdoor dining options for food and drinks under the stars.
Show more
Show less

Top Accommodation Types in Siesta Key

Type Count
Vacation Homes 2002
Holiday Apartments 658
Villas 419
Cottages 63

Use these Quick Filters to Find a Holiday Rental in Siesta 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 Siesta Key.

Weather in Siesta Key, FL

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

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F

Top Attractions Around Siesta Key, FL

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


Siesta Key Beach
Turtle Beach
Crescent Beach
Siesta Key Marina
Point of Rocks
Shell Beach
St. Boniface Episcopal Church Labyrinth
Bay Island
Irma Beach
Jim Neville Marine Preserve
Lido Beach
Venice Beach
St. Armands Circle
IMG Academy
Nokomis Beach
Coquina Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art

Other Places to Stay in Siesta Key, FL


Siesta Key Marina 7,095 Properties
St. Boniface Episcopal Church Labyrinth 7,036 Properties
Crescent Beach 7,010 Properties
Point of Rocks 6,898 Properties
Siesta Key Beach 6,641 Properties
Irma Beach 5,967 Properties
Shell Beach 5,526 Properties
Siesta Key Village 4,329 Properties
Turtle Beach 3,518 Properties
Aloha Kai 165 Properties
Bay Island 48 Properties
Bay Isle 48 Properties

Frequently Asked Questions About Siesta Key?

What are the top holiday rentals in Siesta Key?

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

How many holiday rentals have private pools in Siesta Key?

Discover a selection of holiday rentals with private pools near Siesta 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 Siesta Key are best for families?

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

How many Casai.com holiday rentals are available in Siesta Key?

As of 2025, Casai boasts over 6331 properties listed in the Siesta Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Siesta Key.

Nearby Neighborhood (4) 
Neighborhood Property Count
Siesta Key Village Vacation Rentals in Sarasota, Florida 4329
Aloha Kai Vacation Rentals in Sarasota, Florida 165
South Sarasota Vacation Rentals in Sarasota, Florida 109
Bay Isle Vacation Rentals in Sarasota, Florida 48

People Also Ask

There are 6331 Siesta Key, FL Holiday Rentals

Recently Booked Holiday Rentals in Siesta Key