Siesta Key Vacation Packages

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Your Siesta Key Vacation

Its laid-back lifestyle, laid-back lifestyle and beaches are just the start of the reasons to book a vacation package to Siesta Key. No matter your reason for coming to this Gulf of Mexico city, you're sure to have a fantastic experience. If taking in sights is part of the program during your trip to Siesta Key, visit top attractions like Siesta Key Beach, St. Armands Circle and Mote Marine Laboratory & Aquarium. Don't delay your visit to this destination any longer. Your perfect Siesta Key vacation is only a few clicks away with Expedia.

Top Siesta Key Vacation Deals

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

Bay Palms Waterfront Resort - Hotel and Marina

Belle Vista

CA $832

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.4/10 Very good! (560 reviews)

Cedar Cove Resort and Cottages

CA $1,917

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

Un lugar muy bonito y cómodo para disfrutar en familia lo único es que los sofácama no son cómodos yo tuve que comprar un colchón y solo hay un parqueo por habitación el personal es muy amable la pasamos bien

Reviewed on Sep 16, 2026

voco Sarasota by IHG

Central Sarasota

CA $1,608

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

The hotel is well-located, and well-maintained. The room was clean and spacious. I took advantage of the hotel's relatively small pool, which was fine. The dining area was being renovated, and was only open on weekends (I chose not to dine there). I did not take advantage of the hotel's shuttle to beaches and other nearby amenities. Hotel staff are well-trained and very accommodating. The hotel is walking distance from the commercial area of the downtown, and there are numerous restaurants to choose from. Hotel management, according to staff upon my checkout, apparently would have been gracious in offering to reduce and refund my prepaid reservation by one night of my four night stay due to my airline's extremely delayed plane departure causing a missed airplane connection (and thus a forced overnight stay at the connecting city instead of my reserved day of initial arrival at voco Sarasota). But unfortunately Hotels.Com was unwilling to accommodate my request for the one-night refund.

Reviewed on Sep 13, 2026

The Hotel Zamora

CA $931

per person

Nov 27 - Dec 2

found 15 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

8.8/10 Excellent! (397 reviews)

My wife and I traveled for an anniversary get away. The property was beautiful. The part that as not very pleasant was the fact I called to book a certain room and was walked through it by front desk person who was very helpful on the phone. I did exactly as instructed and then upon arrival was placed in a different accommodation and told. I didn’t book the room that I called in about. I explained who I spoke with and what I was told and the assistance manager on duty seemed upset at me about this issue. Offered no assistance and said no room was available. I asked why the room I booked was still showing available online if it’s not available. Then he proceeded to say oh yes but it’s not ready yet. Then said there was nothing he could do about the person or what they told me and refused any help. Because we had no alternative at this point I paid full price the other room that wasn’t ready yet. He was very uncaring in his attitude and also very rude to employees who all DID provide a high level of service and hospitality our entire stay. Outwardly denigrating them in front of us and other guest. Very poor reflection on an otherwise very good stay at a beautiful hotel. The pool bar was amazing and everyone at the restaurant was absolutely fantastic! Everyone can have a bad day but they don’t have to make it bad for everyone else, especially in hospitality. There shouldn’t be such ugly people in management at such an otherwise dreamy place.

Reviewed on Sep 15, 2026

Bayview Plaza Waterfront Resort

Belle Vista

CA $850

per person

Nov 22 - Nov 27

found 7 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.6/10 Excellent! (582 reviews)

We enjoyed our time there. Staff was excellent. The room clean. Fantastic view.

Reviewed on Aug 26, 2026

Where to stay in Siesta Key

Find the best Siesta Key areas and neighborhoods for the activities you enjoy most. Learn more about Siesta Key

A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village

1 out of top 10 points of interest in this area

Travelers to Siesta Key Village praise its stunning beaches. If you've got some more time to explore, be sure to make a stop by Siesta Key Beach and Siesta Key Farmers Market.

A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.

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.

Things to do in and around Siesta Key

Siesta Key, Florida, is perfect for family vacations, offering stunning beaches and outdoor activities. Visitors can enjoy a variety of adventure activities, explore area attractions, and indulge in golf vacations. The destination features recreational areas, resorts, and shopping mall centres, ensuring there's something for everyone. Whether you're seeking relaxation or adventure, Siesta Key has a range of activities and trips to make your visit memorable.

Shopping

The Siesta Key Farmers Market offers a charming local vibe and is perfect for fresh produce and unique gifts. For more shopping, Gulf Gate Mall is only 4.8km away, boasting various family-friendly shops and entertainment. If you're up for a drive, Artisans' World Marketplace is 6.4km away, featuring unique artisan goods.

Recreation

Experience the vibrant arts at Van Wezel Performing Arts Hall, just 8.0km from Siesta Key, where culture meets entertainment. For sports enthusiasts, Ed Smith Stadium, 9.7km away, buzzes with energy, while Stoneybrook Golf & Country Club, 11.3km distant, offers a serene outdoor golfing experience.

Adventure

Sarasota BayWalk offers a scenic hiking trail that immerses you in the natural beauty of the area, located 6.4km from Siesta Key. For some energetic fun, visit Payne Park Tennis Center, 8.0km away, where you can engage in thrilling tennis matches amidst adventure vibes.

If you're looking for family-friendly excitement, head to Astro Skate and Fun Center, 20.9km from Siesta Key. This arcade adventure zone promises hours of fun with various games and activities, making it a perfect spot for both kids and adults seeking adventure.

Nightlife

Siesta Key offers a vibrant nightlife with beach bars like the Siesta Key Oyster Bar, perfect for live music and fresh seafood. For a lively atmosphere, visit The Beach Club, where you can dance the night away. Enjoy a laid-back evening at Daiquiri Deck with refreshing cocktails.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Siesta Key

Siesta Key, Florida, is perfect for beach lovers and families seeking outdoor adventures. With a variety of attractions, including Siesta Key Village, Siesta Key Beach, and local marinas, visitors can enjoy a delightful mix of relaxation and urban experiences. Whether you're lounging on the sand or exploring nearby parks, Siesta Key offers something for everyone looking to unwind in a beautiful setting.

Siesta Key Beach: Renowned for its powdery white sands and stunning turquoise waters, Siesta Key Beach offers a quintessential beach experience. Relax under the sun, enjoy beach volleyball, or take a leisurely stroll along the shore while soaking in the vibrant atmosphere.
St. Armands Circle: A charming shopping and dining destination located 4.8km from Siesta Key, St. Armands Circle features a mix of upscale boutiques, cafes, and art galleries. Experience the lively city vibes while indulging in gourmet dining and unique shopping.
Marie Selby Botanical Gardens: Situated 6.4km from Siesta Key, these gardens provide a romantic and tranquil escape. Wander through lush tropical landscapes, enjoy the stunning orchid collection, and create lasting memories with family amidst the beauty of nature.

Best time to go to Siesta Key

The best time to visit Siesta Key is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Moderately High	Average
February	65.1°F (18.4°C)	No Rain	Mostly Sunny	Average	Slightly High
March	68.0°F (20.0°C)	No Rain	Sunny	Moderately High	Slightly High
April	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Average	Average
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny	Average	Average
July	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
September	81.5°F (27.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	70.7°F (21.5°C)	No Rain	Mostly Sunny	Moderately Low	Slightly Low
December	66.6°F (19.2°C)	No Rain	Mostly Sunny	Moderately Low	Average

Tips to save on your trip to Siesta Key

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Siesta Key during the low season (August to September and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Siesta Key Beach Vacation

Unwind on the shore while you gaze at the sunlight sparkling on the water during your Siesta Key vacation. If you're yearning for a complete beach experience, a trip to Siesta Key certainly delivers. There's a good chance you've heard of Siesta Key Beach (2 kilometres away). We suggest finding accommodations close by. However, plenty of visitors also opt for Siesta Key vacation packages that are closer to Crescent Beach or Shell Beach, two other superb nearby options.

Things You Should Know About Siesta Key

Spend your getaway by the water and let the stresses and strains of daily life drift away with the sea breeze. Check out our Siesta Key beach hotels and discover beachside bliss.
Our condos, like Hyatt Siesta Key Beach and Siesta Key Inn, are popular with visitors of all sorts. Consider the amenities and get ready for your stay in Siesta Key!
Be sure to visit our Siesta Key things to do page for some trip planning inspiration. With a population of 16,764 cm Siesta Key, we're sure there'll be one or two locals who'll be happy to give you some extra advice!
Turtle Beach, Crescent Beach and Crescent Beach are just some of the attractions that should be on your travel schedule. With our Siesta Key vacation deals, you'll have more money in your pocket to explore.

Ready to book your vacation to Siesta Key?

Choose your dates

Siesta Key Hotel Deals

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

CA $188

CA $249 total

Sep 27 - Sep 28

includes taxes & fees

9.4/10 Exceptional! (5,879 reviews)

"Loved how close the beach was. Very nice swim pool. And neighbors were respectful."

Reviewed on Sep 16, 2026

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

CA $191

CA $293 total

Sep 17 - Sep 18

includes taxes & fees

Cottages at Siesta Key Inn

1105 Point of Rocks Rd Siesta Key FL

Fully refundableReserve now, pay when you stay

CA $171

CA $217 total

Sep 22 - Sep 23

includes taxes & fees

8.6/10 Excellent! (267 reviews)

"Zero help from staff or Expedia customer service to try and cancel my reservation before the location closed because they falsely advertised the age requirement of check-in to be 21 yrs, i received a message then promptly messaged back only to get no reply, no partial refunds either."

Reviewed on Sep 14, 2026

See all 3,984 properties in Siesta Key

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

A sandy beach with people sunbathing and umbrellas, clear blue sky, and calm sea.

Turtle Beach

9.0/10 (1,163 reviews)

If a restful vacation is part of your travel plans, Turtle Beach might be the perfect place to seek out during your trip to Siesta Key. Wander the seaside or discover the sunsets in this relaxing area.

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A sunset over the ocean with silhouettes of people and tall grasses.

Crescent Beach

9.4/10 (815 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.

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A beach with a pier, palm trees, and calm ocean waters under a clear sky.

Point of Rocks

9.2/10 (444 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.

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A marina with boats docked, a clear sky, and a palm tree.

Safe Harbor Siesta Key

9.2/10 (709 reviews)

Explore the waterfront in Siesta Key with a trip to Safe Harbor Siesta Key. Attend a sporting event or simply enjoy the lively bars while you're in the area.

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A coastal town with a beach, marina, and residential area.

Shell Beach

9.2/10 (164 reviews)

Why not spend a lazy afternoon at Shell Beach during your trip to Siesta Key? Wander the beautiful beaches in this relaxing area.

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A beach with people sunbathing, umbrellas, and beach chairs.

Jim Neville Marine Preserve

8.8/10 (71 reviews)

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.

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Siesta Key Beach Playground

Explore the great outdoors at Siesta Key Beach Playground, a lovely green space in Siesta Key. Wander the beautiful beaches in this relaxing area.

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What to do in Siesta Key

Sarasota - Clear Kayak LED Night Glass Bottom Tour

CA $90

per adult

78% of travellers recommend

Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

CA $99

per adult

96% of travellers recommend

Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $82

per adult

94% of travellers recommend

See all activities in Siesta Key

Frequently asked questions

How much does a Siesta Key vacation package cost?

You'll find cheap prices from CA $832 on Expedia for your Siesta Key break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Siesta Key costs.

What are the cheapest months to go to Siesta Key?

You can usually find lower rates and better availability in September, October and November. Check out our cheap Siesta Key vacation packages and you could get some great off-season deals.

How many days is enough for Siesta Key?

Siesta Key vacations come in all shapes and sizes, but to really sink your teeth into this destination, we'd say 4 days is about right. This will mean you can visit top sights like Lido Beach and St. Armands Circle along with hidden gems. Don't forget to visit neighbourhoods such as Central Sarasota and Siesta Key Village either. If you're smart with your time, you can even allow for a day trip or two from Siesta Key too.

Is it worth booking a vacation package to Siesta Key?

Well known for its coastal beaches and home to leading attractions like Bay Island, a Siesta Key vacation is sure to impress. Another top sight to visit? Don't miss Siesta Key Beach.

How to find the best Siesta Key package deals?

Begin your search for a Siesta Key package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Siesta Key package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Siesta Key getaway off to a flying start.

Is it cheaper to book a Siesta Key vacation as a package?

You can enjoy significant savings on your next Siesta Key getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Siesta Key?

If you have your Siesta Key travel dates locked in, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.

How to plan a trip to Siesta Key?

Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Siesta Key.
Budget wisely: In addition to the price of your stay, you should factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Siesta Key.
Decide your trip length: Consider how long you'd like to spend exploring Siesta Key. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Siesta Key vacation package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Siesta Key Vacation

Top Siesta Key Vacation Deals

Bay Palms Waterfront Resort - Hotel and Marina

Cedar Cove Resort and Cottages

voco Sarasota by IHG

The Hotel Zamora

Bayview Plaza Waterfront Resort

Where to stay in Siesta Key

Siesta Key Village

South Village

Aloha Kai

Bailey Hall

Point of Rocks

Things to do in and around Siesta Key

Find the best attractions in and around Siesta Key

Best time to go to Siesta Key

Tips to save on your trip to Siesta Key

Siesta Key Beach Vacation

Things You Should Know About Siesta Key

Ready to book your vacation to Siesta Key?

Siesta Key Hotel Deals

Tropical Beach Resorts

Siesta Key Beach Resort and Suites

Cottages at Siesta Key Inn

Stay near popular Siesta Key attractions

Siesta Key Beach

Turtle Beach

Crescent Beach

Point of Rocks

Safe Harbor Siesta Key

Shell Beach

Jim Neville Marine Preserve

Siesta Key Beach Playground

What to do in Siesta Key

Sarasota - Clear Kayak LED Night Glass Bottom Tour

Siesta Key Electric Bike Sunset Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

Frequently asked questions

Explore a world of travel with Expedia

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