Find Vacation Rentals in Siesta Key

Highlights Siesta Key

  • Beach activities
  • Sandy beaches
  • Clear water
  • Golf
  • Mild weather

Best Vacation Rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.
Siesta Key, Sarasota County
Vacation Rental • 1292 ft² • 2 Bedrooms
(7 reviews)
The condo is on the third floor balcony facing south overlooking the mediterainian garden. At almost 1400 square feet, the apartment features 2 bedrooms and two bathrooms, a large sunny living room with balcony. The kitchen holds all the equipment that the hobby chef needs. The large 3D-TV with AppleTV and sound system in the living room and flat screen TVs in both bedrooms provide entertainment. WiFi, air conditioning, washer and dryer are standard.
from $261 / night
Siesta Key, Sarasota County
Vacation Rental • 6 Guests • 2 Bedrooms
(10 reviews)
This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout. Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing evenings and memorable chats under the stars. Please note, there is a one-week minimum stay. Siesta Dunes Beach is a resort packed with amenities, ...
from $249 / night
Siesta Key Beach, Siesta Key
Vacation Rental • 6 Guests • 2 Bedrooms
(24 reviews)
In this handy ground-floor condo, you're just a short walk away from gorgeous Crescent Beach, the jewel in Siesta Key's crown. Enjoy laid-back beach living, from the open-air patio to the sun-washed living room! Jamaica Royale 91 redefines "easy." No stairs, no hallways, no fuss -- just walk right up and you're in! The patio will lure you right away, with its ultra-comfy chaise longues and chairs--sturdy, yet lightweight enough to be easily moved to follow the sun or shade as the day progresses. Wreathed in palm trees and tropical foliage, this is your private haven in Florida's most beaut...
from $181 / night

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Prices and availability

Vacation rental prices Siesta Key

$586for 11 Feb - 18 Feb
$496 annual average
Average price per week

Vacation rentals availability Siesta Key

7%for 11 Feb - 18 Feb
42% annual average
Percentage of available rentals

Siesta Key Vacation Rentals

Seafront Vacation Villas

Siesta Key is home to hundreds of beautiful and spacious vacation homes. Located along the stunning Florida coastline with close proximity to the ocean, your vacation rental may feature a private pool, terrace, private garden and beach access. You will find dozens of beautiful beach villas close to the popular Siesta Beach area and the city centre at Sarasota. You can opt for a rental home on Ocean Boulevard which include oceanfront villas and homes which are just a few minutes walk from the beach.

Rural Retreats and Holiday Villages

There are many different vacation home styles on the stunning stretch of land that makes up the Siesta Key area. You can choose from large modern homes, light and airy condominiums, bed and breakfast accommodation or opt for the convenience of resort accommodation. Homes are equipped with all the modern conveniences and located close to the best attractions, landmarks and event locations in Siesta Key. Your rental home also gives convenient access to malls, banks, shops, restaurants and sporting facilities in Siesta Key and the greater Florida area.

Vacationing in Siesta Key

Barrier Island with Sandy Beaches

Siesta Key is located on the coast of Florida. The area is a barrier island sandwiched between Roberts Bay and the Gulf of Mexico on the central western Florida coast. The island is 8 miles long and crescent-shaped. Siesta Key is connected to Sarasota by two bridges. The area is known for its unique white sand. The sand is 99% pure quartz and always stays cool underfoot. that stays cool under your feet.

Barrier Island Dominated by Beaches

The key is dominated by beautiful beaches including Turtle Beach, Siesta Beach and Crescent Beach. Siesta Key is located 55 miles south of Tampa, Florida. A segment of the key forms part of Sarasota city, but most of the key is in Sarasota County

A Great Beach Town

Many people choose to visit Siesta Key for its proximity to the beach and relaxation potential. Siesta Beach is located close to the cafes and shops and offers safe, shallow waters for children, a playground and tennis courts. The Crescent Beach area is linked to limestone outcrops at the Point of Rocks, where you will also find tidal pools and coral reefs. There are boat ramps and picnic spots at Turtle Beach.

Siesta Beach
Siesta Beach


Outdoor Adventures on Siesta Key p>Choosing to rent a vacation home on Siesta Key is a great choice for lovers of adventure and the outdoors. You can choose to rent a fishing charter, go kite swimming, parasailing, cycling or kayaking on the river. Paddleboarding is a popular activity in the area and you can jetski, surf or skateboard with the whole family.

The Ideal Spa Holiday Destination

The area's peaceful and relaxing aura is only enhanced when you opt for a spa vacation or stay at one of the spa resorts in the area. There are several spas in the area that offer wellness treatments, warm water therapies and massage with essential oils and herbal ingredients. There are retreats which offer yoga, taichi and guided meditation for guests.

A Swimmers Paradise

The Siesta Key area offers very calm seas with not much big wave action so this can be ideal for those who love to swim or families that want to play in the water. The area is ideal for families with younger children for this reason. The beach offers crystal clear water and good swimming during summer

Siesta Key Sunset
Siesta Key Sunset

Top 5 things to do in Siesta Key

1. Glebe Park

A true gem of Siesta Key- Glebe Park is a green zone where families can relax, run, play soccer and cycle. Mothers push their babies in strollers, kids run around and the Suncoast Sports Club runs a soccer program from the park. Off the beaten path from the tourism aspect of Siesta Key, this is a hidden treasure.

2. Cocoanut Bayou

Cocoanut Bayou includes Little Pond Lane, Cedar Park Circle, Higel Avenue and Mangrove Point where you can find a great vacation rental. The area is well known for its beautiful natural vistas and peaceful aspect. The Cocoanut Bayou is all about rest and relaxation and getting away from it.

3. Siesta Key Drum Circle

The Siesta Key Drum Circle is a regular event every Sunday evening at Sunset Beach. Visitors and locals, from young to old enjoy the rhythms of the drums as they watch the sunset and the lively atmosphere spills over into the waves.

4. Play Golf

Siesta Key is a great location for playing golf. Golf courses are located in a great area of the key with magnificent views. Try the Legacy Golf Club or Serenoa Golf Club, for a great golfing destination.

5.Marie Selby Botanical Gardens

The Marie Selby Botanical Gardens is a popular attraction on Siesta Key. This wonderful and historic walking area offers wonderful lush gardens to enjoy, a stunning orchid collection and well-informed staff.

Siesta Beach was voted the nation's number one beach in 2001. The beach sand is 99% quartz and there are 800 parking spots in the beach parking lot.

Useful Information

Mild climate

Siesta Key has some amazing weather to enjoy. The winter months offer good weather when most of the rest of the country are snowy and cold. Summer days are hot, but on Siesta Key you can enjoy the Gulf breezes that seem to be present for much of the year.

Siesta Fiesta

Held for the past 39 years, the Siesta Fiesta is an art and craft festival enjoyed by locals and tourists alike. Visitors can stroll up and down the beach and marvel at the different arts and crafts on offer. Designed and made by the community of Siesta Key, this is a very popular event.

FAQs: Vacation Rentals in Siesta Key

On average, what was the cost for vacation rentals in Siesta Key last year?

Our data shows that Siesta Key had an average price of $382 per night, a relatively high one for a city in the USA.

During which months are vacation rentals cheaper in Siesta Key?

Travelers who want to save as much as possible travel to Siesta Key in October, September, or May, the cheapest months of the year, with average prices of $329, $342, and $350 per night, respectively, based on the previous year.

When does the price of vacation rentals in Siesta Key go up the most?

When it comes to looking for a vacation rental in Siesta Key, the months when it is most expensive are, in order of highest to lowest, March, February and April, with average prices per night of $482, $466, and $414, respectively.

Do I need to plan a trip to Siesta Key well in advance?

It is recommended that you book your stay well in advance when visiting Siesta Key, as only 9% of our accommodations are usually available throughout the year.

Which months offer the highest availability?

September, August and October are, in order of highest to lowest, the months that have the largest number of properties available, with an average availability of 20%, 20%, and 16%. However, even during these months, when rental availability is the highest, the average is just 19%. So it is still important you always book a little in advance to make sure you get the rental of your dreams.

During which months is it more difficult to find available vacation rentals?

The accommodations in Siesta Key reach their peak in demand in February, with an availability rate of 1%. The second most requested month is March, with 1%, and the third is June with 2%. During these three months, the availability is only 1%. It is therefore recommended to book far in advance.

Are there many vacation rentals in Siesta Key?

In Siesta Key we work with 11 different providers to give you a choice of 410 properties, so you will not be short of options!

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