Siesta Key Vacation Packages 2026 from $644

Siesta Key flight + hotel vacation packages

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

Cedar Cove Resort and Cottages

Save 100% on your flight

$644

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop 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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$953

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

Captiva Beach Resort

South Village

Save 100% on your flight

$1,017

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

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.

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$743

per person

Sep 1 - Sep 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$755

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

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

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$198 total

Aug 10 - Aug 11

Total with taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a library, and a picnic area are also on offer.

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$266 nightly

$301 total

Aug 9 - Aug 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.

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$240 total

Aug 25 - Aug 26

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.

Azul Resort Siesta Key

1105 Point of Rocks Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$201 total

Aug 25 - Aug 26

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.

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$246 nightly

$278 total

Aug 23 - Aug 24

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.

Captiva Beach Resort

6772 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$193 total

Aug 10 - Aug 11

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.

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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.

Stay near popular Siesta Key attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 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.

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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 $644. 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.