Siesta Key Vacation Packages 2026 from $601

Siesta Key flight + hotel vacation packages

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

voco Sarasota by IHG

Central Sarasota

$601

per person

Jul 13 - Jul 18

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, along with express check-out. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Avalon Club

Save 100% on your flight

$854

per person

Jun 12 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,201

per person

Jul 13 - Jul 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Pelican Pointe Clearwater Beach Hotel

Save 100% on your flight

$805

per person

Jul 31 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and laundry facilities.

Little Gull Cottages by Coolvacay

Save 100% on your flight

$1,562

per person

Jul 18 - Jul 25

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. A picnic area and barbecue grills are also provided.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$208 total

May 20 - May 21

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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$273 nightly

$308 total

May 31 - Jun 1

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

$199 nightly

$225 total

May 13 - May 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

Azul Resort Siesta Key

1105 Point of Rocks Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$208 total

May 13 - May 14

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace is also provided.

Pool

Pet friendly

Siesta Key Island Rentals

515 Beach Rd Siesta Key FL

$326 nightly

$369 total

May 13 - May 14

Total with taxes and fees

This vacation home features laundry facilities. Take advantage of the free self parking.

Washer

Dryer

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$263 nightly

$297 total

May 13 - May 14

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.

Pool

Free WiFi

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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 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.

Jim Neville Marine Preserve

Explore the great outdoors at Jim Neville Marine Preserve and enjoy the beautiful sunsets during your trip to 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 $601. 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.