Siesta Key Village Vacation Packages

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Top Holiday Package Deals in Siesta Key Village

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,657, price is now CA $955 per person
CA $955
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay! Friendly staff. Spacious suites. Pet friendly. Heated pool.

Reviewed on Jan 31, 2026

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was CA $6,704, price is now CA $3,343 per person
CA $3,343
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sarasota (SRQ)
9.6/10 Exceptional! (45 reviews)
The room was exactly as shown, plenty of room to stretch out and we especially loved the end unit. Steps from the beach and shelling was perfect! Grounds were raked each morning with umbrellas taken down each day. Nice cushions on the lounge chairs, deck furniture and the beach towels were nice & fluffy. A great lil refrigerator, we would have liked a coffee maker, rather than a cappuccino and the coffees offered were strong. No microwave. Bathroom with a lovely rain-head was favorable. We definitely recommend and it is located in a desirable area.

Reviewed on Jan 24, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $2,137, price is now CA $1,136 per person
CA $1,136
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (1,156 reviews)
4 times I encountered cockroaches in the room. One time scurrying across my foot while in the bathroom. Doubtful I’ll ever come back here.

Reviewed on Feb 5, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Price was CA $2,779, price is now CA $1,663 per person
CA $1,663
per person
Apr 11 - Apr 18
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,355 reviews)
Furniture was very old/ dirty and couch was broken.

Reviewed on Jan 14, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,617, price is now CA $978 per person
CA $978
per person
Apr 11 - Apr 18
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
The room was clean. Comfortable bed. Kitchenette. Beautiful view of the water. Can watch the birds. Close to stores, restaurant, St. Pete beach, Tampa bay, and old Tampa bay, and other sites. The city of St. Petersburg and Tampa.

Reviewed on Jan 24, 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
Unbelievable sugar white sand beach, beautiful place to visit.

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 Siesta Key Marina and Crescent Beach.

Find hotels in South Village

Siesta Key Village Hotel Deals

Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd. Siesta Key FL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Feb 8 to Feb 9
CA $273
CA $345 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Staff were wonderful. Room clean.

Reviewed on Feb 1, 2026

Tropical Breeze Resort
Siesta Key Beachside Villas

Siesta Key Beachside Villas

2.5 out of 5
124 Columbus Blvd Siesta Key FL
The price is CA $457 per night from Feb 10 to Feb 11
CA $457
CA $593 total
Feb 10 - Feb 11
includes taxes & fees
8.8/10 Excellent! (913 reviews)
The room and grounds were well kept and clean. Proximity to beach and many restaurants was excellent. Pool was warm and clean. Use of chairs and beach towels was an awesome perk and free water bottles, ice and cooler (to use) was an added bonus. Only thing I was surprised about was no room cleaning, ...

Reviewed on Jan 31, 2026

Siesta Key Beachside Villas
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd Siesta Key FL
The price is CA $717 per night from Feb 15 to Feb 16
CA $717
CA $887 total
Feb 15 - Feb 16
includes taxes & fees
8.8/10 Excellent! (1,059 reviews)
Our bedroom and living area were big and the unit was very clean. The location is perfect! Walkable to the beach and lots of restaurants & shops. Only downfall is the bathrooms are small.

Reviewed on Jan 28, 2026

Siesta Key Beach Resort and Suites
See all 13,621 properties in Siesta Key Village
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.
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Frequently asked questions

How much does a Siesta Key Village vacation package cost?
Less than you might think — from just CA $955, 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.

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

CA $82
per adult
92% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

CA $90
per adult
80% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

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

CA $90
per adult
84% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
See all activities in Siesta Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.