Siesta Key Vacation Packages 2026 from $494

Siesta Key flight + hotel vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$494

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

CW Hotel

Save 100% on your flight

$1,272

per person

Aug 13 - Aug 18

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 hot tub and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Villa Valentino Luxury 8BR Villa & Pool

Allen's Ridge

Save 100% on your flight

$2,619

per person

Aug 20 - Aug 24

found 2 days ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this villa. WiFi in public areas is free. A terrace, a garden, and barbecue grills are also on offer.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,084

per person

Aug 10 - Aug 16

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

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 Fold Hotels Indian Shores

Save 100% on your flight

$788

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, a terrace, and laundry facilities are also on offer.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

$226 nightly

$256 total

Jun 15 - Jun 16

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

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$241 nightly

$273 total

Jun 24 - Jun 25

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

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$198 nightly

$224 total

Jun 11 - Jun 12

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

Azul Resort Siesta Key

1105 Point of Rocks Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$184 total

Jun 14 - Jun 15

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace is also provided.

Pool

Pet friendly

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$242 nightly

$273 total

Jul 5 - Jul 6

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

Siesta Key Island Rentals

515 Beach Rd Siesta Key FL

$319 nightly

$361 total

Jun 11 - Jun 12

Total with taxes and fees

This vacation home features laundry facilities. Take advantage of the free self parking.

Washer

Dryer

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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 Beach

4.5/5(1,449 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(150 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.

Siesta Key Marina

4.5/5(375 reviews)

Explore the waterfront in Siesta Key with a trip to Siesta Key Marina. 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 $494. 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.