Siesta Key Vacation Packages 2026 from $276

Siesta Key flight + hotel vacation packages

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

Lemon Bay Motel

Englewood Central

Save 100% on your flight

$276

per person

Mar 16 - Mar 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Pelican Post at Anna Maria Island Inn

$1,653

per person

Feb 22 - Feb 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This apartment features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden is also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,264

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

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.

Mar Bay Motel &Suites

Save 100% on your flight

$832

per person

Mar 7 - Mar 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,343

per person

Mar 27 - Apr 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$192 nightly

$217 total

Jan 27 - Jan 28

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

$255 nightly

$288 total

Jan 29 - Jan 30

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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$257 nightly

$290 total

Jan 25 - Jan 26

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

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$339 nightly

$383 total

Jan 25 - Jan 26

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

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$235 nightly

$266 total

Jan 25 - Jan 26

Total with taxes and fees

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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

915 Seaside Drive Siesta Key FL

Free Cancellation

$404 nightly

$457 total

Jan 28 - Jan 29

Total with taxes and fees

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

Siesta Key Public Beach showing a sandy 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.

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 $276. 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.