Book Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key

Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd, Siesta Key, FL
With a stay at Siesta Key Island Rentals in Siesta Key, you'll be a 1-minute drive from Siesta Key Beach and 9 minutes from Sarasota Memorial Hospital.
Siesta Key Island Rentals
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key
With a stay at this vacation home, you'll be centrally located in Siesta Key, steps from Siesta Key Beach and within a 5-minute drive of Crescent Beach.
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Close to Beach Access #7, Short Walk to the Village

Close to Beach Access #7, Short Walk to the Village

Siesta Key
With a stay at this vacation home in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 5 minutes from Crescent Beach.
Close to Beach Access #7, Short Walk to the Village
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Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

Siesta Key
The price is AU$1,661 per night from 15 Apr to 16 Apr
AU$1,661
includes taxes & fees
15 Apr - 16 Apr
With a stay at this vacation home, you'll be centrally located in Siesta Key, a 1-minute drive from Siesta Key Beach and 9 minutes from Sarasota Memorial ...
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
SKV 315 -  Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

Siesta Key
With a stay at this vacation home in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 6 minutes from Crescent Beach.
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

Sarasota
With a stay at this vacation home, you'll be centrally located in Sarasota, a 4-minute drive from Crescent Beach and 5 minutes from Siesta Key Beach.
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Stunning Siesta Key,,  .  , Walk to Shell Beach, HEATED POOL - Discounts

Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts

Sarasota
With a stay at this vacation home in Siesta Key (Bay Isle), you'll be within a 5-minute drive of Siesta Key Beach and Sarasota Memorial Hospital.
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
With a stay at this vacation home in Siesta Key, you'll be a 1-minute drive from Siesta Key Beach and 9 minutes from Crescent Beach.
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!

SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!

Siesta Key
With a stay at this vacation home in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 6 minutes from Crescent Beach.
SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Siesta Key Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Siesta Key vacation homes are the perfect way for you to wing it.

Holiday houses in Siesta Key let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Siesta Key in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Siesta Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Siesta Key with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Siesta Key vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Siesta Key Holiday Homes essential information

Accommodation
804 Holiday Homes
Lowest Price
AU$401
Highest Price
AU$1,661
Popular accommodation
Siesta Key Island Rentals, SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND, Close to Beach Access #7, Short Walk to the Village, Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village, SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!, Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.), Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts, Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool, SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!

Top trending hotels in Siesta Key

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$401 per night from 1 May to 2 May
AU$401
includes taxes & fees
1 May - 2 May
With a stay at Tropical Beach Resorts in Siesta Key, you'll be in the business district, within a 10-minute walk of Siesta Key Marina and Crescent Beach.
Tropical Beach Resorts
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
The price is AU$621 per night from 8 Apr to 9 Apr
AU$621
includes taxes & fees
8 Apr - 9 Apr
With a stay at Siesta Key Beach Resort and Suites in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 6 minutes from Crescent ...
Siesta Key Beach Resort and Suites
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$770 per night from 21 Apr to 22 Apr
AU$770
includes taxes & fees
21 Apr - 22 Apr
With a stay at Tropical Breeze Resort in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 8 minutes from Sarasota Memorial ...
Tropical Breeze Resort
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The Ringling Beach House

The Ringling Beach House

3.5 out of 5
523 Beach Road, Siesta Key, FL
The price is AU$727 per night from 3 Apr to 4 Apr
AU$727
includes taxes & fees
3 Apr - 4 Apr
With a stay at The Ringling Beach House in Siesta Key, you'll be in a shopping district, steps from Siesta Key Beach and a 5-minute drive from Crescent ...
The Ringling Beach House
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.