Pennington Place Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Pennington Place

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was CA $2,189, price is now CA $1,465 per person
CA $1,465
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
9/10 Wonderful! (913 reviews)
Very convenient to athletic fields

Reviewed on Jan 12, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $3,742, price is now CA $2,312 per person
CA $2,312
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
9.2/10 Wonderful! (480 reviews)
Everything was perfect cant wait to go back

Reviewed on Feb 10, 2026

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Price was CA $5,768, price is now CA $3,926 per person
CA $3,926
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
9.4/10 Exceptional! (286 reviews)
Room was great, location was great, pool area was very clean and well kept, access to the beach was the icing on the cake. Highly recommend this resort.

Reviewed on Feb 22, 2026

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was CA $4,327, price is now CA $2,991 per person
CA $2,991
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
8.6/10 Excellent! (636 reviews)
Room was super clean . Staffs were nice , accessible to swimming pool and beach easily. Got house keeping everyday to clean and organize the room. We. Loved it . Free rides to go anywhere within the island .

Reviewed on Feb 23, 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
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Venice Island

5 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 Brohard Paw Park.

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 $328 per night from Feb 24 to Feb 25
CA $328
CA $406 total
Feb 24 - Feb 25
includes taxes & fees
9.4/10 Exceptional! (5,325 reviews)
clean room, staff was extremely friendly and helpful, was able to hold our luggage all day once we checked out. Property was clean and so close to beach!

Reviewed on Feb 23, 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 $344 per night from Mar 22 to Mar 23
CA $344
CA $388 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,939 reviews)
the room was clean, the pool and bar were great. Bartender was so friendly and recommended some great places to visit. It the perfect hotel right across from Siesta Key.

Reviewed on Feb 23, 2026

Spark by Hilton Sarasota Siesta Key Gateway
Days Inn by Wyndham Sarasota I-75

Days Inn by Wyndham Sarasota I-75

2 out of 5
5774 Clark Rd Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Mar 22 to Mar 23
CA $166
CA $188 total
Mar 22 - Mar 23
includes taxes & fees
6.6/10 (590 reviews)
yes--robot for a desk person--not always understanding of a request but was very courteous cleaners missed us one day and we were without toilet paper and towels. nothing major great rooms and Diego the live desk person that was there sparingly was a great person

Reviewed on Feb 23, 2026

Days Inn by Wyndham Sarasota I-75
See all 7,605 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 $1,465, 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 featuring general coastal views and a sandy beach

Venice Beach

4.5/5(31 reviews)

If a restful vacation is part of your travel plans, Venice Beach might be the perfect place to seek out during your trip to Venice.

Venice Beach
Sarasota_CaspersenBeach_553248621533115772-4

Caspersen Beach

4.5/5(2 reviews)

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 which includes a sandy beach and general coastal views as well as a couple

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

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

CA $80
per adult
94% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Siesta Key Guided Eco Tour

Siesta Key Guided Eco Tour

CA $80
per adult
100% of travellers recommend
Siesta Key Guided Eco 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.