Siesta Key Vacations 2026 from CA $769

Siesta Key flight + hotel packages

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

Pelican Pointe Clearwater Beach Hotel

CA $769

per person

Jun 22 - Jun 25

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, laundry facilities, and cable TV channels. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

The Avalon Club

CA $1,455

per person

Jun 22 - Jun 25

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Wyndham Grand Clearwater Beach

CA $1,001

per person

Jun 22 - Jun 25

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

ChartHouse Clearwater Beach Marina Hotel

CA $829

per person

Jun 22 - Jun 25

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Waterfront Resort Condo Gulf Sun Set

CA $1,194

per person

Jun 24 - Jun 27

found 23 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

Stay at this aparthotel in Dunedin. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Top Siesta Key hotels deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free cancellation

Reserve now, pay when you stay

CA $220

CA $284 total

May 20 - May 21

includes taxes & fees

Book a stay at this beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

CA $270

CA $381 total

May 31 - Jun 1

includes taxes & fees

Stay at this resort in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free cancellation

Reserve now, pay when you stay

CA $225

CA $284 total

May 25 - May 26

includes taxes & fees

Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Azul Resort Siesta Key

1105 Point of Rocks Rd Siesta Key FL

Free cancellation

Reserve now, pay when you stay

CA $248

CA $280 total

May 26 - May 27

includes taxes & fees

Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Pool

Pet-friendly

Siesta Key Island Rentals

515 Beach Rd Siesta Key FL

Get rates

Stay at this vacation home in Siesta Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Washer

Dryer

Siesta Key Beachside Villas

124 Columbus Blvd Siesta Key FL

Free cancellation

Reserve now, pay when you stay

CA $259

CA $368 total

May 17 - May 18

includes taxes & fees

Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

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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

Nothing says vacation like spending a lazy day at Siesta Key Beach, a popular beach in Siesta Key. Amble around this quaint area's seaside or experience its live music.

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.

Jim Neville Marine Preserve

Explore the great outdoors at Jim Neville Marine Preserve and enjoy the beautiful sunsets during your trip to 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 CA $769. 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.