Cheap Siesta Key Vacation Packages

You’re on the hunt for a steal of a deal on your Siesta Key vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Siesta Key hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Siesta Key vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Siesta Key for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Siesta Key?

When you want to book the very best Siesta Key getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Siesta Key for as low as $234 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Siesta Key?

Looking to save some extra cash on your Siesta Key vacation? Try going on your getaway in , which is the off-season, and avoid the most popular time to vacation in the month of . Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

How to get the best vacation package deals to Siesta Key?

If scoring the very best deal on your Siesta Key vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

What is the cheapest day to book a vacation package?

Reserving a Siesta Key vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $234.

Can I vacation in Siesta Key right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Siesta Key right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

What does Hotwire Siesta Key travel package include?

When you book a package deal on Hotwire, you can expect a Siesta Key vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.

Siesta Key Flight + Hotel Packages

Alden Suites - A Beachfront Resort

Save 100% on your flight

per person

Dec 3 - Dec 5

Roundtrip flight included

Chicago (ORD) to Tampa (TPA)

This St. Pete Beach hotel is on the beach, 4.6 mi (7.4 km) from John's Pass Village & Boardwalk, and within 12 mi (20 km) of Eckerd College and Fort De Soto Park. Tropicana Field and Salvador Dali Museum are also within 12 mi (20 km).

Sunset Vistas Two Bedroom Beachfront Suites

Save 100% on your flight

per person

Dec 30 - Jan 6

Roundtrip non-stop flight included

Milwaukee (MKE) to Tampa (TPA)

This Treasure Island condo resort is on the beach, 0.6 mi (1 km) from John's Pass Village & Boardwalk, and within 12 mi (20 km) of Tropicana Field and Mahaffey Theater. Museum of Fine Arts and Sunken Gardens are also within 12 mi (20 km).

Innisbrook, A Salamander Golf & Spa Resort

per person

Dec 30 - Jan 6

Roundtrip non-stop flight included

Milwaukee (MKE) to Tampa (TPA)

Located in Palm Harbor, this family-friendly resort is 0.9 mi (1.4 km) from Wall Springs Park, and within 6 mi (10 km) of Anderson Park and St Nicholas Greek Orthodox Cathedral. Tarpon Springs Sponge Docks and John Chesnut Sr Park are also within 12 mi (20 km).

Wyndham Grand Clearwater Beach

Save 100% on your flight

per person

Dec 28 - Jan 3

Roundtrip flight included

Nashville (BNA) to Tampa (TPA)

Nestled on the beach, this Clearwater Beach hotel is within a 5-minute walk of Pier 60 Park, Clearwater Beach, and Clearwater Municipal Marina. Beach Walk and Captain Blighs Landing are also within 15 minutes.

Kompose Boutique Hotel

per person

Dec 7 - Dec 11

Roundtrip flight included

Nashville (BNA) to Tampa (TPA)

Situated near the airport, this hotel is within a 10-minute walk of Ca’ d’Zan, Sarasota Classic Car Museum, and Asolo Theatre for the Performing Arts. Sarasota Kennel Club and John and Mable Ringling Museum of Art are also within 15 minutes.

Crystal Palms Beach Resort

per person

Dec 30 - Jan 6

Roundtrip non-stop flight included

Milwaukee (MKE) to Tampa (TPA)

Situated near the beach, this aparthotel is within a 10-minute walk of St. Petersburg Municipal Beach and Dolphin Marine Rentals. John's Pass Village & Boardwalk and Hubbards Marina are also within 1 mi (2 km).

Holiday Inn Sarasota Airport, an IHG Hotel

per person

Nov 19 - Nov 24

Roundtrip non-stop flight included

Chicago (ORD) to Tampa (TPA)

Situated in Sarasota, this hotel is within 3 mi (5 km) of Sarasota Kennel Club, Sarasota Classic Car Museum, and Asolo Theatre for the Performing Arts. Ca’ d’Zan and John and Mable Ringling Museum of Art are also within 3 mi (5 km).

Casey Key Resorts - Beachfront

per person

Nov 19 - Nov 24

Roundtrip non-stop flight included

Chicago (ORD) to Sarasota (SRQ)

Nestled on the beach, this Nokomis hotel is within 1 mi (2 km) of Nokomis Beach and North Jetty Beach. Venice Beach and Caspersen Beach are also within 9 mi (15 km).

Siesta Key Vacation Packages 3-4 Night Stays

3.0-star property

Winter the Dolphins Beach Club, Ascend Hotel Collection

Dec 11 - Dec 15

1 night stay

Washington (IAD) to Tampa (TPA)

Delta • Non-stop • Coach

Tampa (TPA) to Washington (IAD)

United • Non-stop • Coach

per person

4.0-star property

TradeWinds Island Grand

Dec 11 - Dec 15

1 night stay

Washington (IAD) to Tampa (TPA)

Delta • Non-stop • Coach

Tampa (TPA) to Washington (IAD)

United • Non-stop • Coach

per person

3.5-star property

RumFish Beach Resort by TradeWinds

Dec 11 - Dec 15

1 night stay

Washington (IAD) to Tampa (TPA)

Delta • Non-stop • Coach

Tampa (TPA) to Washington (IAD)

United • Non-stop • Coach

per person

3.5-star property

Edge Hotel Clearwater Beach

Dec 11 - Dec 15

1 night stay

Washington (IAD) to Tampa (TPA)

Delta • Non-stop • Coach

Tampa (TPA) to Washington (IAD)

United • Non-stop • Coach

per person