Siesta Key Vacation Packages 2025/2026 from $529

Siesta Key flight + hotel vacation packages

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

Family Home Tampa

Forest Hills

$529

per person

Jan 28 - Feb 2

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Sarasota (SRQ)

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

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$758

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Sarasota (SRQ)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like a free area shuttle.

The Avalon Club

Save 100% on your flight

$729

per person

Feb 8 - Feb 13

found 9 hours ago

Roundtrip flight included

Cincinnati (CVG) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$857

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Sarasota (SRQ)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the outdoor pool and conveniences like a 24-hour front desk and wedding services.

Sailport Waterfront Suites

Rocky Point

Save 100% on your flight

$834

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Sarasota (SRQ)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and snack bar/deli.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$185 total

Nov 16 - Nov 17

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

$237 nightly

$267 total

Nov 18 - Nov 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

Captiva Beach Resort

6772 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$170 total

Nov 16 - Nov 17

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

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$270 total

Nov 17 - Nov 18

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 dry cleaning 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

$384 nightly

$434 total

Dec 8 - Dec 9

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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$243 nightly

$275 total

Dec 7 - Dec 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

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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.

Point of Rocks

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 $529. 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.