Siesta Key Vacations from $383

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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.

The Latest Siesta Key vacation packages

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

Clearwater Suites

2.5 out of 5
Save 100% on your flight
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.8/10 Excellent! (12 reviews)
Nice very spacious room. Close tobthe beach and restaurants.

Reviewed on Aug 11, 2025

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
8.8/10 Excellent! (2,044 reviews)
The elevator was broken

Reviewed on Aug 13, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.4/10 Exceptional! (2,470 reviews)
Room wasn't cleaned or any additional water provided during our stay - we had to ask for water each day and even toilet roll. There wasn't any turndown service. The beds on the beach should be provided to reflect the number of occupants I the room. Lifts aways had a long wait. Staff were generally very polite and the main parts of the hotel were nice. Good location for the beach, pier 60 and shops restaurants away from the hotels.

Reviewed on Aug 13, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
As a travel agent I have traveled extensively and reviewed a plethora of properties. I would highly recommend Ocean Club. The check in area is small but it gets the job done. All condos are gulf front with beautiful views. Previous reviews remarked about the music from the pool- we were in room 206 which is almost directly above the pool and we didn’t have a problem. The actual Condo is very clean with everything you need for your stay- pots and pans, dishes, can opener, toaster, keurig (complete with a variety of pods), quality towels, and comfortable beds. There is also a full size washer and dryer in each unit. Others also remarked about “the trek” to the beach. Please remember that the waterline on a beach is variable and building codes require structures to be specific distances from the beach. Additionally, Florida law prohibits the destruction of certain grasses and sea oats. You can rent chairs and umbrellas on the beach OR there are plenty of umbrellas, chairs, sand toys,and floats that are in a communal area left by previous guests. There is a limit to one car per unit and with this parking is free. WiFi can be spotty as my partner did have to use her hotspot in order to work from our unit.

Reviewed on Aug 12, 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.2/10 Very Good! (1,345 reviews)
Needs some upgrades on current rooms, but we had a great stay there

Reviewed on Aug 11, 2025

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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
Siesta Key Village

Siesta Key Village

1 out of top 10 points of interest in this area
4.5/5(282 area reviews)

Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.

Find hotels in Siesta Key Village

Discover the most popular places to visit in Siesta Key

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

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.

Siesta Key Beach
Crescent Beach

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.

Crescent Beach

Point of Rocks

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.

Point of Rocks

What to do in Siesta Key

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$55
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

$375
per traveler
100% of travellers recommend
Private Luxury Boat Charter
Siesta Key Guided Eco Tour

Siesta Key Guided Eco Tour

$59
per adult
100% of travellers recommend
Siesta Key Guided Eco Tour
See all activities in Siesta Key

Siesta Key Hotel Deals

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
$159 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (4,858 reviews)
Spectacular mini stay !
"The resort was truly fantastic! The pool was stunning, and we captured some breathtaking photos. The service was excellent, making our stay even more enjoyable. My only minor issue was with the shower—the water didn't get cool enough, and the faucet didn't fully switch to the showerhead. Aside from ..."

Reviewed on Aug 12, 2025

Tropical Beach Resorts
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $215 total per night from Sep 1 to Sep 2
$215 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,013 reviews)
"Loved the unit and how close we were to everything we wanted to do. Will most definitely be back."

Reviewed on Aug 13, 2025

Tropical Breeze Resort
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
$214 nightly
The price is $241 total per night from Sep 1 to Sep 2
$241 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Really nice and accommodating"

Reviewed on Aug 11, 2025

Siesta Key Beach Resort and Suites
See all 3,854 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.

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 (1 mile 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 6,600 in 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.

Things to do in and around Siesta Key

Siesta Key offers a perfect blend of beach and outdoor activities for families. Visitors can enjoy kayaking tours, play tennis at local courts, and explore hidden beaches. Don't miss the chance to shop at popular mall centers or unwind at resorts. For a memorable experience, consider the best vacation packages and create a sightseeing list to discover the area’s natural beauty and attractions.

Shopping

For a delightful shopping experience in Siesta Key, visit the Siesta Key Farmers Market for local goods. Gulf Gate Mall, 3 miles away, offers a variety of shops and entertainment. If you're up for a drive, check out Artisans' World Marketplace, located 4 miles from Siesta Key.

Recreation

At Van Wezel Performing Arts Hall, immerse yourself in captivating performances that blend culture and romance, just 5 miles from Siesta Key. Ed Smith Stadium, 6 miles away, offers an energetic atmosphere for sports enthusiasts, while Gulf Gate Golf Club, 4 miles from Siesta Key, invites you to enjoy outdoor golfing adventures.

Adventure

Explore the scenic Sarasota BayWalk, a beautiful hiking trail 4 miles from Siesta Key, offering breathtaking views and outdoor adventure. For family fun, visit the Astro Skate and Fun Center, an arcade 13 miles away. Additionally, enjoy tennis at the Payne Park Tennis Center, located 5 miles from Siesta Key.

Nightlife

Siesta Key's nightlife offers a vibrant atmosphere with beachfront bars like the Siesta Key Oyster Bar and lively venues such as The Beach Club. Enjoy live music, dancing, and delicious cocktails while soaking in the laid-back charm of this beautiful coastal paradise.

*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 an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore popular attractions like Siesta Key Beach, Siesta Key Palms, and the local marina, while enjoying the area's urban parks. Whether you're looking for a relaxing day by the water or a vibrant city experience, Siesta Key offers a variety of activities that cater to all types of travelers.

  • Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beachcombing. The stunning sunsets provide a picturesque backdrop, making it an idyllic spot for relaxation and fun.
  • St. Armands Circle: A vibrant shopping and dining destination, St. Armands Circle is filled with unique boutiques, galleries, and restaurants. Enjoy a leisurely stroll around the circle, where you can savor delicious cuisine while soaking in the lively city vibes.
  • Marina Jack: This bustling marina provides opportunities for outdoor adventures, including boat rentals and fishing charters. With beautiful waterfront views, it's a great place to enjoy fresh seafood and experience the local beach culture.

Best time to go to Siesta Key

The best time to visit Siesta Key can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Siesta Key falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Siesta Key falls in January, visitor numbers are moderately high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighAverage
February65.1°F (18.4°C)No RainMostly SunnyAverageSlightly High
March68.0°F (20.0°C)No RainSunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighAverage
August83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
September81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowAverage
November70.7°F (21.5°C)No RainMostly SunnyModerately LowSlightly Low
December66.6°F (19.2°C)No RainMostly SunnyModerately LowAverage

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 during the off-peak season (typically August to September and November) for more affordable package holidays to Siesta Key.
  • 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.

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Frequently asked questions

How much does a Siesta Key vacation package cost?
Offering great value package deals from $383 on Expedia, you'll be surprised at how little a vacation to Siesta Key costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Siesta Key?
You can typically find reduced prices and greater availability in September, October and December. Take a look at our cheap Siesta Key vacation packages and you could score some excellent off-season deals.
How many days is enough for Siesta Key?
With around 4 days, you'll have enough time to enjoy popular neighborhoods like Central Sarasota and Newtown during your Siesta Key vacation. Remember to also add Shell Beach and Irma Beach to your sightseeing list. Up for some more adventures? Consider exploring outside of Siesta Key on day trips and tours.
Is it worth booking a vacation package to Siesta Key?
Well known for its coastal beaches and home to popular attractions like Siesta Key Beach, a Siesta Key vacation is bound to impress. Another top sight worth exploring? Don't miss Crescent Beach.
How to find the best Siesta Key package deals?
Start your search for a Siesta Key package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Siesta Key package deal straight away, simply change 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 escape 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 escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Siesta Key?
If you have your Siesta Key travel dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to a 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?

  1. Choose your dates: The things you'd like to do in Siesta Key and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Siesta Key.
  3. Organize your Siesta Key getaway with Expedia's trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Siesta Key together.
  4. Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Siesta Key. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Siesta Key vacation package.
  6. Add on excursions and experiences: Take a look at our travel guide to find some awesome things to do in Siesta Key. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Siesta Key vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Siesta Key trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.