Siesta Key Village Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Siesta Key Village
Price found within the past 48 hours. Click for updated prices.
CW Resort
CA $1,461
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
The room
Was clean. Very nice layout . If you order from the restaurant make sure all of your condiments and utensils are in the bag. They forgot it every time we order from them, but besides the minor inconveniences we
Would definitely stay again.
Reviewed on Oct 5, 2026
Cedar Cove Resort and Cottages
CA $2,313
per person
Nov 7 - Nov 14
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (603 reviews)
So clean and anything at all that we needed the staff was more than willing to do great experience
Reviewed on Oct 4, 2026
Where to stay in Siesta Key Village
Find the best Siesta Key Village areas and neighborhoods for the activities you enjoy most. Learn more about Siesta Key Village
South Village
1 out of top 10 points of interest in this area
While visiting South Village, you might make a stop by sights like Safe Harbor Siesta Key and Crescent Beach.
Aloha Kai
While Aloha Kai isn't home to many top sights, Siesta Key Beach and Crescent Beach are some notable places to visit nearby.
Bailey Hall
When in Bailey Hall, you can plan a visit to Siesta Key Beach and Lido Beach, some noteworthy sights in the nearby area.
Point of Rocks
While there might not be top attractions in Point of Rocks, you can explore the larger area and discover places like Siesta Key Beach and Point of Rocks.
White Beach
When in White Beach, you can plan a visit to Point of Rocks and Safe Harbor Siesta Key, some noteworthy sights in the nearby area.
Siesta Key Village Hotel Deals
Siesta Key Beach Resort and Suites
5311 Ocean Blvd Siesta Key FL
CA $208
CA $314 total
Oct 6 - Oct 7
includes taxes & fees
9.2/10 Wonderful! (1,187 reviews)
"This resort was amazing. Our room was prefect. So clean, had everything we needed to enjoy our stay. The staff was incredible. We meant wonderful people at the pool. I’m looking forward to going back to this place."
Reviewed on Oct 5, 2026
Tropical Breeze Resort
140 Columbus Blvd. Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $212
CA $268 total
Oct 7 - Oct 8
includes taxes & fees
8.8/10 Excellent! (1,029 reviews)
"Location is great if you want to be close to all the shopping and restaurants . Also walking distance to the beach. Property is good in general. But it was a big let down when we walked in the bedroom and saw the bed with a bunch of hair. Specially the pillows. We had to go back to the front desk ..."
Reviewed on Oct 4, 2026
Siesta Key Beachside Villas
124 Columbus Blvd Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $190
CA $294 total
Oct 6 - Oct 7
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Very nice property. It's close to all the shops and restaurants in Siesta Key village... and the beach. The room was clean and comfortable. A nice experience overall."
Reviewed on Oct 4, 2026
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.
Frequently asked questions
How much does a Siesta Key Village vacation package cost?
Less than you might think — from just CA $1,461, in fact! By combining hotels, flights and car rentals into a custom-made travel package, your trip to Siesta Key Village is just clicks away.
How do I get a cheap travel package to Siesta Key Village?
Combining your hotel and flight with Expedia won't just save you time — it'll save you money too. A Siesta Key Village vacation package makes it simple to create your ideal trip. With more than 550 airlines throughout the world to choose from, finding flights that suit your busy schedule won't be difficult. In addition to that, we've got over 1,000,000 hotel options globally to pick from. Now that's what you call choice. No matter who you are, Expedia will help show you the world.
Where should I stay in Siesta Key Village?
If you want to be where the action is, stay somewhere close to Siesta Key Beach. Many visitors book a hotel around this famous tourist attraction.
What are the top hotels in Siesta Key Village?
If it's your first time in Siesta Key Village, lock in a room at Siesta Beach Cottage or Siesta Key 2bedroom /1bath Villa Barefoot Bungalows. Both hotels will make you feel at home and are favorites with many travelers.
How far in advance should I book my Siesta Key Village vacation?
Travelers are usually able to compare international fares on Expedia up to 12 months prior to departure. Booking last minute? With a little bit of luck, it's still possible to score a cheaper ticket only weeks before your flight.
What does an Expedia Siesta Key Village travel package include?
It's up to you! You can choose from a variety of Siesta Key Village packages, such as a flight, rental car and hotel. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your perfect Siesta Key Village break looks like, you'll save!
What should I know before booking a Siesta Key Village travel package?
Design deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your escape. You'll save loads just for bundling your bookings. Whether you're embarking on a ski trip or kicking back on a warm beach, your perfect vacation is just a few clicks away.
Can I choose my airline with a Siesta Key Village Expedia vacation package?
Yes — that's the beauty of an Expedia package. You get to choose. We have more than 550 airline partners across the globe, so you have lots of choice when planning your Siesta Key Village adventure.
If I'm not able to travel, can I cancel my Siesta Key Village vacation package?
Yes, you can cancel your Siesta Key Village booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
Stay near popular Siesta Key Village attractions
Siesta Key Farmers Market
You can enjoy retail therapy at Siesta Key Farmers Market during your trip to Siesta Key. Amble around this quaint area's beautiful beaches and enjoy its lively bars.
Things to do
Siesta Key Electric Bike Sunset Tour
CA $100
per adult
96% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $83
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
CA $83
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.