Siesta Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel South Tampa & Suites

Hotel South Tampa & Suites

Virginia Park
CA $1,105
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
8.6/10 Excellent! (1,929 reviews)
Clean room

Reviewed on Oct 12, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
CA $2,850
per person
Dec 29 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
CA $4,675
per person
Dec 29 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
Property was great. Loved the location. On the quieter side but close to everything

Reviewed on Oct 13, 2026

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

Save 100% on your flight
CA $2,098
per person
Dec 29 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (485 reviews)
BeachTrail Lodging

BeachTrail Lodging

Save 100% on your flight
CA $1,743
per person
Dec 16 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.8/10 Exceptional! (101 reviews)
The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well.

Reviewed on Apr 14, 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 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.

Find hotels in South Village
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.

Find hotels in Siesta Key Village
Default Image

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.

Find hotels in Aloha Kai
Default Image

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.

Find hotels in Point of Rocks
Default Image

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.

Find hotels in Bailey Hall

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.

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 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

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $181
CA $241 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (5,970 reviews)
"Amazing pool. Very large suite."

Reviewed on Oct 14, 2026

Tropical Beach Resorts
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL
CA $208
CA $314 total
Nov 3 - Nov 4
includes taxes & fees
9.2/10 Wonderful! (1,190 reviews)
"Everything was perfect. Pool, staff,close to everything. Shops, bars, restaurants and beach"

Reviewed on Oct 12, 2026

Siesta Key Beach Resort and Suites
Cottages at Siesta Key Inn

Cottages at Siesta Key Inn

1105 Point of Rocks Rd Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $197
CA $250 total
Oct 20 - Oct 21
includes taxes & fees
8.8/10 Excellent! (283 reviews)
"Room was clean. Parking right outside. Perfect for our one night stay."

Reviewed on Oct 10, 2026

Cottages at Siesta Key Inn
See all 4,245 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

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.
See properties
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.
See properties
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.
See properties
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.
See properties
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.
See properties
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.
See properties
A lifeguard tower with green and yellow colors, stairs, and a beach in the background.

Irma Beach

8.4/10 (66 reviews)
Why not spend a lazy afternoon at Irma Beach during your trip to Siesta Key? Wander the beautiful beaches in this relaxing area.
See properties

What to do in Siesta Key

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

CA $91
per adult
86% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

CA $100
per adult
96% of travellers recommend
Siesta Key Electric Bike Sunset Tour
Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $83
per adult
96% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
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 $1,105 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

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