Siesta Key Vacation Packages 2026 from $639

Siesta Key flight + hotel vacation packages

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

Captiva Beach Resort

South Village

Save 100% on your flight

$639

per person

Nov 29 - Dec 4

found 23 hours ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

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

Sunshine Beach

Save 100% on your flight

$717

per person

Nov 5 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

CW Resort

Save 100% on your flight

$655

per person

Nov 5 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

Cedar Cove Resort and Cottages

Save 100% on your flight

$823

per person

Dec 12 - Dec 16

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$1,971

per person

Dec 8 - Dec 15

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$179 total

Sep 27 - Sep 28

Total with taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A library, a picnic area, and luggage storage are also on offer.

Pool

Kitchen

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$195 nightly

$220 total

Sep 21 - Sep 22

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

Cottages at Siesta Key Inn

1105 Point of Rocks Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$148 total

Sep 21 - Sep 22

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

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$202 total

Sep 22 - Sep 23

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

SeaSpray Resort

574 Canal Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$247 total

Sep 22 - Sep 23

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.

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$234 total

Sep 21 - Sep 22

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.

Stay near popular Siesta Key attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 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.

See properties

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 $639. 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.