Pennington Place Vacation Packages

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Top Holiday Package Deals in Pennington Place

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was CA $840, price is now CA $777 per person
CA $777
per person
Jul 31 - Aug 3
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
8.8/10 Excellent! (1,188 reviews)
Place was very clean and quiet close to store’s restaurant and beach

Reviewed on Jun 16, 2026

Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was CA $1,609, price is now CA $1,450 per person
CA $1,450
per person
Jul 31 - Aug 3
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
8.8/10 Excellent! (1,005 reviews)
Loved that we were steps from the beach and we had chairs and an umbrella waiting for us every day. The gentleman that got them out was so helpful and very nice. Our room was clean and well decorated. The local restaurants were all amazing. The food and entertainment were all good. Pops, Pelican Alley and Rosebud’s. Love Casey Key and the beautiful blue water.

Reviewed on Jun 18, 2026

Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was CA $940, price is now CA $892 per person
CA $892
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.2/10 Wonderful! (444 reviews)
The rooms are big , clean and very confortable.

Reviewed on Jun 2, 2026

Home2 Suites by Hilton Nokomis Sarasota Casey Key

Home2 Suites by Hilton Nokomis Sarasota Casey Key

3 out of 5
Price was CA $1,350, price is now CA $1,308 per person
CA $1,308
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sarasota (SRQ)
9.2/10 Wonderful! (907 reviews)
The breakfast could have been better but the staff was amazing

Reviewed on Jun 17, 2026

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
Price was CA $1,277, price is now CA $1,240 per person
CA $1,240
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sarasota (SRQ)
9.4/10 Exceptional! (506 reviews)
Staff was amazing! Helpful and friendly.

Reviewed on Jun 19, 2026

Where to stay in Pennington Place

Find the best Pennington Place areas and neighborhoods for the activities you enjoy most. Learn more about Pennington Place
Beautiful sunset on Siesta Key, Florida

Venice Island

4 out of top 10 points of interest in this area

While visiting Venice Island, you might make a stop by sights like Venice Beach and Caspersen Beach.

Find hotels in Venice Island

Pennington Place Hotel Deals

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Jun 28 to Jun 29
CA $263
CA $367 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (5,578 reviews)
"On a holiday the hotel had no night live time. At 8 pm was dead and you can’t make any type of noise around 9 pm because all the guest are sleeping according to the staff. I believe this hotel is for like retired guest that come to read and sleep. The bbq are which you can seat down and talk or play ..."

Reviewed on Jun 19, 2026

Tropical Beach Resorts
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Jun 24 to Jun 25
CA $198
CA $224 total
Jun 24 - Jun 25
includes taxes & fees
8.4/10 Very Good! (2,158 reviews)
"Friendly, quiet, Close to restaurants"

Reviewed on Jun 18, 2026

Spark by Hilton Sarasota Siesta Key Gateway
Azul Resort Siesta Key

Azul Resort Siesta Key

3 out of 5
1105 Point of Rocks Rd Siesta Key FL
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Jun 22 to Jun 23
CA $219
CA $248 total
Jun 22 - Jun 23
includes taxes & fees
8.8/10 Excellent! (171 reviews)
"We visited in mid june 2026 very clean confortable room within walking distance to the beach, the room comes with an assign parking spot, every room comes with a small table and two chairs just outside the room which we used often and luckily it was always shaded, you can borrow beach chairs but ..."

Reviewed on Jun 15, 2026

Azul Resort Siesta Key
See all 7,679 properties in Pennington Place
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 Pennington Place vacation package cost?
Our Pennington Place vacation packages, which begin at just CA $777, are an easy way to save. Select your preferred hotels, flights and rental car to create your dream getaway.
How do I get a cheap travel package to Pennington Place?
Our Pennington Place vacation packages offer plenty of savings for the savvy wanderer. For the best deals, simply bundle your flights, hotels and rental cars into a neat and tidy package. But low prices are only the start of your next unforgettable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to select from. Whatever your budget, there's a vacation package that's perfect for you.
Where should I stay in Pennington Place?
Cross Venice Beach off your bucket list and then stay right around the corner. Experience the buzzing vibe around this terrific attraction and visit whenever you please!
How far in advance should I book my Pennington Place vacation?
To bag discount prices, book ASAP. Airlines usually advertise flights, along with some of the lowest fares, around 12 months prior to departure. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Pennington Place, there are always lots of great bargains to be had on Expedia. Check them out now!
What does an Expedia Pennington Place travel package include?
That depends on what you want. If you're traveling solo, you might decide to bundle flights and hotels. Bringing the whole family to Pennington Place? A travel package including hotels, rental cars and flights might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Pennington Place travel package?
You'll score impressive savings when you combine your flights, hotels and rental cars into a package. Plus, booking everything in one place simply makes planning easier. So why waste time or money? Whether you're organizing a ritzy romantic getaway or a low-cost family road trip, have a look at our package deals today.
Can I choose my airline with a Pennington Place Expedia vacation package?
You can, and with more than 550 airlines to pick from worldwide, you have loads of choice. Search the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Pennington Place vacation package?
We get that sometimes life doesn't go according to plan. If you've locked in a Pennington Place vacation package and need to cancel or change it, we're here to help. We suggest browsing our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary free of charge. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.

Discover the most popular places to visit in Pennington Place

Venice Beach

Venice Beach

Nothing says vacation like spending a lazy day at Venice Beach, a popular beach in Venice Island.

Venice Beach
Sarasota_CaspersenBeach_553248621533115772-4

Caspersen Beach

If a restful vacation is part of your travel plans, Caspersen Beach might be the perfect place to seek out during your trip to Venice. Attend a sporting event in the area, or seek out the biking trails.

Caspersen Beach
Venice Fishing Pier

Venice Fishing Pier

After visiting Venice Fishing Pier, make a plan to see the other sights and activities in Venice. Stroll along the beautiful beaches in this family-friendly area, or check out its lively bars.

Venice Fishing Pier

Things to do

Venice Clear Kayak Glass Bottom LED Night Tour

Venice Clear Kayak Glass Bottom LED Night Tour

CA $97
per adult
100% of travellers recommend
Venice Clear Kayak Glass Bottom LED Night Tour
See all activities in Venice
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.