Siesta Key Vacation Packages 2025 from $458

Siesta Key flight + hotel vacation packages

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

Captiva Beach Resort

Save 100% on your flight

per person

Jul 14 - Jul 17

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

The Avalon Club

Save 100% on your flight

per person

Aug 14 - Aug 18

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Cedar Cove Resort and Cottages

Save 100% on your flight

per person

Jul 6 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Sarasota (SRQ)

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.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

per person

Aug 14 - Aug 19

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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

$169 nightly

$191 total

Jun 2 - Jun 3

Total includes taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.

Pool

Kitchen

Siesta Key Beach Resort and Suites

5311 Ocean Blvd, Siesta Key, FL

$271 nightly

$307 total

Jun 2 - Jun 3

Total includes 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

$289 nightly

$327 total

Jun 2 - Jun 3

Total includes 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 a picnic area are also on offer.

Pool

Hot Tub

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Get rates

A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities.

Pool

Hot Tub

The Ringling Beach House

523 Beach Road, Siesta Key, FL

$351 nightly

$397 total

Jun 8 - Jun 9

Total includes taxes and fees

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

The Residences at Siesta Key Beach by Hyatt Vacation Club

915 Seaside Drive, Siesta Key, FL

$720 nightly

$814 total

Jun 3 - Jun 4

Total includes taxes and fees

This aparthotel features an outdoor pool and a 24-hour gym. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free valet parking.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Siesta Key

View all properties

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 quaint 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 $458. 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.