Siesta Key Vacation Packages 2026 from $399

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

$399

per person

Mar 22 - Mar 27

found 3 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Delray House With Hot tub & Game Room

Palm River-Clair Mel

Save 100% on your flight

$563

per person

Mar 12 - Mar 18

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, free self parking, and a virtual front desk are featured at this vacation home. Dry cleaning is also provided.

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Town 'n' Country

$582

per person

Mar 12 - Mar 18

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A full-service spa, free self parking, and laundry facilities are featured at this villa. Barbecue grills and a virtual front desk are also provided.

Family Home Tampa

Forest Hills

Save 100% on your flight

$708

per person

Mar 10 - Mar 15

found 6 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Tampa (TPA)

This guesthouse includes a garden and a virtual front desk. Take advantage of the free self parking.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,668

per person

Mar 12 - Mar 18

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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

$144 nightly

$185 total

Jan 7 - Jan 8

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

$206 nightly

$250 total

Jan 7 - Jan 8

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

$221 nightly

$305 total

Jan 7 - Jan 8

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

$188 nightly

$237 total

Jan 13 - Jan 14

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

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$271 nightly

$307 total

Jan 19 - Jan 20

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

The Residences at Siesta Key Beach by Hyatt Vacation Club

915 Seaside Drive Siesta Key FL

Free Cancellation

$407 nightly

$511 total

Feb 5 - Feb 6

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.

Pool

Breakfast included

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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

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.

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.

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.

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 $399. 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.