Siesta Key Vacation Packages 2025/2026 from $301

Siesta Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Zoo House Down Town Tampa

Riverbend

$301

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

The Avalon Club

$905

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$475

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Bayview Plaza Waterfront Resort

Belle Vista

$440

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A marina and an outdoor pool are featured at this smoke-free hotel. Spend a day at the beach kayaking, or relax with beach cabanas and sun loungers. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.

Innisbrook Resort

Save 100% on your flight

$1,478

per person

Jan 10 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This Tudor resort features a golf course, a full-service spa, and 4 restaurants. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 6 outdoor pools and perks like free WiFi.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$181 nightly

$204 total

Nov 9 - Nov 10

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A garden, a library, and a picnic area are also on offer.

Pool

Kitchen

Tropical Breeze Resort

140 Columbus Blvd., Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$237 nightly

$267 total

Nov 6 - Nov 7

Total with taxes and fees

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Hot Tub

Captiva Beach Resort

6772 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$187 total

Nov 6 - Nov 7

Total with taxes and fees

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

Kitchen

SeaSpray Resort

574 Canal Rd, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$281 total

Nov 30 - Dec 1

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A garden, a picnic area, and dry cleaning are also on offer.

Pool

Pet friendly

Siesta Key Beach Resort and Suites

5311 Ocean Blvd, Siesta Key, FL

$255 nightly

$288 total

Nov 6 - Nov 7

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free WiFi. Self parking, a terrace, and a garden are also offered.

Pool

Hot Tub

The Ringling Beach House

523 Beach Road, Siesta Key, FL

Get rates

An outdoor pool, free self parking, and concierge services are featured at this apartment. WiFi in public areas is free. A terrace, a garden, and a library are also on offer.

Pool

Kitchen

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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

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

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.

Crescent Beach

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.

Point of Rocks

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.

Frequently asked questions

How much are vacation packages to Siesta Key?

You can pick up a great hotel and flight bundle for as little as $301. With one of our Travelocity vacation packages, an escape to Siesta Key has never looked so enticing! Save your time and money and then start packing those bags.

Where can I get the best vacation package deals for Siesta Key?

You'll find an amazing range of Siesta Key package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 properties worldwide, putting together the ultimate escape will be a breeze.

Why should I book my Siesta Key vacation bundle with Travelocity?

We have experiences and destinations to suit every kind of globetrotter, excellent service and 24/7 customer support. On top of that, we'll match any lower price you happen to find with our Price Match Guarantee.

Can I save money on my Siesta Key car rental if I combine it with a hotel or flight?

You sure can with our Siesta Key vacation packages. With one of these, there are loads of ways to make your vacation budget go further. Bundle any two or more car, flight, hotel and tour bookings and watch the savings pile up. With your own set of wheels, all the popular sights in and around Siesta Key are a fun road trip away.