Deals on vacations and trips to Siesta Key

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Siesta Key flight + hotel vacation packages

Chestnut Villas Down Town Tampa

Chestnut Villas Down Town Tampa

3 out of 5
Price was $433, price is now $340 per person
per person
Nov 2 - Nov 4
Roundtrip flight included
New York (JFK) to Tampa (TPA)
This villa features a picnic area, laundry facilities, and free self parking. A virtual front desk are provided for your convenience.
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Downtown Tampa
Price was $343, price is now $283 per person
per person
Nov 2 - Nov 4
Roundtrip flight included
New York (JFK) to Tampa (TPA)
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the laundry service, conference space, and valet parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Gulf Strand Resort

Gulf Strand Resort

3 out of 5
Save 100% on your flightPrice was $943, price is now $803 per person
per person
Nov 5 - Nov 11
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
This vacation home features an outdoor pool and a spa tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a library, and a picnic area are also on offer.
Holiday Inn Tampa Westshore - Airport Area, an IHG Hotel

Holiday Inn Tampa Westshore - Airport Area, an IHG Hotel

3 out of 5
Westshore
Price was $311, price is now $266 per person
per person
Nov 2 - Nov 4
Roundtrip flight included
New York (JFK) to Tampa (TPA)
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the spa tub and perks like a free area shuttle.
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Rocky Point
Save 100% on your flightPrice was $701, price is now $614 per person
per person
Nov 5 - Nov 11
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Prices and availability subject to change. Additional terms may apply.

Top Siesta Key hotels deals

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
The price is $106 per night
$106
per night
Oct 19 - Oct 20
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. A garden, a library, and a picnic area are also on offer.
Pool
Parking included
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 $148 per night
$148
per night
Oct 2 - Oct 3
This motel features an outdoor pool and a spa tub. WiFi in public areas is free. Self parking, a terrace, and a garden are also offered.
Hot Tub
Pet friendly
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
The price is $200 per night
$200
per night
Oct 2 - Oct 3
This hotel's 2 outdoor pools and spa tub are among the featured amenities. Families will appreciate the children's pool and onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.
Hot Tub
Pet friendly
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
6772 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
The price is $145 per night
$145
per night
Oct 2 - Oct 3
A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.
Pool
Parking included
Siesta Key Beachside Villas

Siesta Key Beachside Villas

2.5 out of 5
124 Columbus Blvd, Siesta Key, FL
The price is $153 per night
$153
per night
Oct 2 - Oct 3
An outdoor pool, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.
Pet friendly
Pool
The Cottages at Siesta Key

The Cottages at Siesta Key

2.5 out of 5
1105 Point of Rocks Rd, Siesta Key, FL
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. Dry cleaning and barbecue grills are also provided.
Pet friendly
Pool
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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.

Popular places to visit

Image for Siesta Key Beach

Siesta Key Beach

4.5/5(1,425 reviews)

The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

Siesta Key Beach
Image for Crescent Beach

Crescent Beach

4.5/5(146 reviews)

Why not spend a carefree afternoon at Crescent Beach during your travels in Siesta Key? Stroll along the seaside or discover the sunsets in this relaxing area.

Crescent Beach
Image for Point of Rocks

Point of Rocks

4.5/5(31 reviews)

Enjoy the beautiful sunsets and explore Point of Rocks, a lovely green space in Siesta Key. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Point of Rocks

Frequently asked questions

How much are vacation packages to Siesta Key?
With a Travelocity vacation package, you can be living it up in Siesta Key for only $266. Hotels, adventures and flights — we’ve got you. You’ll make great savings just by bundling together your bookings. And with everything taken care of before you go, you don’t have to worry about a thing.
Where can I get the best vacation package deals for Siesta Key?
With around 400 airlines and 1,000,000 hotels across the world, you can’t beat Travelocity. Look through our comprehensive range and create the perfect Siesta Key vacation package. Isn’t it amazing when travel is that easy?
Why should I book my Siesta Key vacation package with Travelocity?
Because life is all about the journey, and we have everything you need to help you along the way. With our top-notch service and Price Match Guarantee, you can book with confidence. And you can rest easy on the road knowing you can reach us with our round-the-clock support.
Will I save money on my Siesta Key car rental if I combine it with a hotel or flight?
Definitely. And our Siesta Key vacation packages are the perfect way to do it. In only a few clicks you can save money and time by bundling your bookings. Collect the keys to your rental car and do your vacation your way. Searching for things to do? Throw some tours or experiences into your package and make savings on those too.
What is the best time of year to go to Siesta Key?
Vacationing during the quietest months of the year, September, October and December, has its upsides — think cheap flights and hotels and less pushing past hordes of strangers. But there’s magic in the air in the peak season. More events will be planned and more attractions will be open in January, July and August. If you want to stretch your budget, typically has the most affordable hotel rates. Expect to pay more for a room in .