Book Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key

Coastal Cottage - Direct Beach Access

Coastal Cottage - Direct Beach Access

Siesta Key, FL
Book a stay at this beach vacation home in Siesta Key. Enjoy a beach locale, a water park, and balconies. Popular attractions Siesta Key Beach and Lido Beach ...
Opens in a new windowCoastal Cottage - Direct Beach Access
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key, FL
Book a stay at this family-friendly vacation home in Siesta Key. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Siesta Key Beach ...
Opens in a new windowSiesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Siesta Key
Book a stay at this beach vacation home in Siesta Key. Enjoy free WiFi, a beach locale, and an in-room coffeemaker. Popular attractions Siesta Key Beach and ...
Opens in a new windowSiesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
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Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 out of 5
8254 Midnight Pass Rd, Siesta Key, FL
Stay at this 3.5-star vacation home in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Turtle Beach are located ...
Opens in a new windowSiesta Heron Suites & Villas
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

Siesta Key
Book a stay at this family-friendly vacation home in Siesta Key. Enjoy private pools, a water park, and laundry facilities. Popular attractions Siesta Key Beach ...
Opens in a new windowPrivate Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key
Stay at this vacation home in Siesta Key. Enjoy free WiFi, a fitness center, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowSiesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

Siesta Key
Book a stay at this family-friendly vacation home in Siesta Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Siesta Key ...
Opens in a new windowSiesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Newly renovated TH in Siesta Key FL - #1 beach in US

Newly renovated TH in Siesta Key FL - #1 beach in US

Siesta Key
Stay at this vacation home in Siesta Key. Enjoy private pools, a fitness center, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach ...
Opens in a new windowNewly renovated TH in Siesta Key FL - #1 beach in US
2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach

Sarasota
The price is NZ$423 per night from 2 Nov to 3 Nov
NZ$423
2 Nov - 3 Nov
includes taxes & fees
Stay at this vacation home in Sarasota. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Siesta Key Beach and Lido Beach are ...
Opens in a new window2 Bedroom 2 Bath home near Siesta Key Beach
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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
891 Holiday Homes
Lowest Price
NZ$354
Highest Price
NZ$648
Popular accommodation
Coastal Cottage - Direct Beach Access, Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village, Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!, Siesta Heron Suites & Villas, Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West, Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL", Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows, Newly renovated TH in Siesta Key FL - #1 beach in US, 2 Bedroom 2 Bath home near Siesta Key Beach

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 NZ$354 per night from 2 Nov to 3 Nov
NZ$354
2 Nov - 3 Nov
includes taxes & fees
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Opens in a new windowTropical Beach Resorts
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 NZ$648 per night from 30 Nov to 1 Dec
NZ$648
30 Nov - 1 Dec
includes taxes & fees
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowTropical Breeze Resort
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
6772 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowCaptiva Beach Resort
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SeaSpray Resort

SeaSpray Resort

4 out of 5
574 Canal Rd, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$490 per night from 2 Nov to 3 Nov
NZ$490
2 Nov - 3 Nov
includes taxes & fees
Stay at this 4-star aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are ...
Opens in a new windowSeaSpray Resort
Don't see what you're looking for?
See all available properties in Siesta Key
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.