Siesta Key Vacation Packages 2025/2026 from $349

Siesta Key flight + hotel vacation packages

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

Mar Bay Motel &Suites

$349

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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 Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$2,262

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip non-stop 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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$736

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Captiva Beach Resort

South Village

Save 100% on your flight

$974

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

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.

Coral Reef Beach Resort

Save 100% on your flight

$638

per person

Jan 8 - Jan 14

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This apartment features 2 outdoor pools and 3 hot tubs. Business travelers can take advantage of the free WiFi in public areas. Free self parking, laundry facilities, and a virtual front desk 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

$166 total

per night

Oct 19 - Oct 20

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

$267 total

per night

Oct 19 - Oct 20

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

$262 total

per night

Oct 19 - Oct 20

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

Captiva Beach Resort

6772 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$187 total

per night

Oct 19 - Oct 20

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

$259 total

per night

Oct 20 - Oct 21

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 Ringling Beach House

523 Beach Road, Siesta Key, FL

Get rates

An outdoor pool, free self parking, and concierge services are featured at this apartment. WiFi in public areas is free. A terrace, a garden, and a library are also on offer.

Pool

Kitchen

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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 $349. 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.