Siesta Key Vacation Packages 2025/2026 from $401

Siesta Key flight + hotel vacation packages

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

Venice Beach Villas

Save 100% on your flight

per person

Oct 10 - Oct 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Enjoy the outdoor pool and conveniences like a terrace and laundry facilities.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

per person

Oct 10 - Oct 15

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

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Oct 8 - Oct 12

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.

EVEN Hotel Sarasota-Lakewood Ranch by IHG

Save 100% on your flight

per person

Oct 10 - Oct 15

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 gym and perks like free self parking and free WiFi. A business center, express check-in, and express check-out are also on offer.

Barsala At The Wayland Condos

Save 100% on your flight

per person

Oct 14 - Oct 18

found 15 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

$164 nightly

$185 total

Aug 3 - Aug 4

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

$269 nightly

$304 total

Aug 12 - Aug 13

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

$250 nightly

$282 total

Jul 30 - Jul 31

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 luggage storage are also on offer.

Pool

Hot Tub

SeaSpray Resort

574 Canal Rd, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$276 nightly

$312 total

Aug 4 - Aug 5

Total includes 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

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

$1,929 nightly

$2,151 total

Jul 27 - Jul 28

Total includes taxes and fees

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

Captiva Beach Resort

6772 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$220 total

Aug 6 - Aug 7

Total includes 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

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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 relaxing 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 $401. 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.