Siesta Key Vacation Packages 2026/2026 from $1,006

Siesta Key flight + hotel vacation packages

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

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$1,006

per person

Feb 14 - Feb 21

found 2 hours ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.

Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,356

per person

Jan 9 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A full-service spa and an outdoor pool are featured at this smoke-free resort. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. There's a poolside bar on site, and laundry facilities and concierge services are also provided.

The Beachcomber

Save 100% on your flight

$1,021

per person

Feb 12 - Feb 17

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

This smoke-free hotel features a nightclub, 2 outdoor pools, and a restaurant. Enjoy a day at the beach parasailing, or relax with sun loungers. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,210

per person

Mar 4 - Mar 8

found 2 hours ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,130

per person

Feb 12 - Feb 17

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$175 total

Dec 9 - Dec 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

Captiva Beach Resort

6772 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$171 total

Dec 18 - Dec 19

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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$247 nightly

$279 total

Dec 9 - Dec 10

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

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$189 total

Dec 18 - Dec 19

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

The Residences at Siesta Key Beach by Hyatt Vacation Club

915 Seaside Drive Siesta Key FL

Free Cancellation

$454 nightly

$513 total

Dec 16 - Dec 17

Total with taxes and fees

A private beach and an outdoor pool are featured at this smoke-free aparthotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$281 total

Dec 9 - Dec 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 picnic area, and express check-in are also on offer.

Pool

Pet friendly

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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 quaint area.

Siesta Key Marina

Explore the waterfront in Siesta Key with a trip to Siesta Key Marina. 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 $1,006. 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.