Siesta Key Vacation Packages 2026 from $388

Siesta Key flight + hotel vacation packages

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

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$388

per person

May 4 - May 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Captiva Beach Resort

South Village

Save 100% on your flight

$479

per person

May 4 - May 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

The Avalon Club

Save 100% on your flight

$999

per person

Apr 19 - Apr 24

found 18 hours ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

$1,922

per person

Apr 20 - Apr 24

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 hotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

Save 100% on your flight

$439

per person

May 4 - May 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

This smoke-free hotel features 3 outdoor pools, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A poolside bar, a 24-hour front desk, and a terrace are also provided.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$326 nightly

$395 total

Feb 18 - Feb 19

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

$294 nightly

$372 total

Feb 18 - Feb 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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$420 nightly

$530 total

Feb 18 - Feb 19

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

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$489 nightly

$553 total

Feb 23 - Feb 24

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 express check-in are also on offer.

Pool

Pet friendly

Captiva Beach Resort

6772 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$296 nightly

$352 total

Feb 18 - Feb 19

Total with taxes and fees

Pool

Kitchen

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$472 nightly

$589 total

Mar 8 - Mar 9

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.

Pool

Free WiFi

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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

Siesta Key Public Beach showing a sandy beach

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 $388. 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.