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.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $1,045, price is now CA $769 per person
CA $769
per person
May 28 - May 31
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
9/10 Wonderful! (1,207 reviews)
Upon arriving at the resort, found this place to be charming. Our room had a kitchenette with small dining table and 4 chairs, 2 queen beds - which were very comfortable and a nice bathroom. The court yard was lovely! The pool was nice as well! Beach access about a 3-4 minute walk away from the resort. Lastly, I want to give a shoutout to the staff in the office. They could not have been nicer! Plan on booking another stay at Captive Beach resort next year.

Reviewed on Feb 21, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,366, price is now CA $1,583 per person
CA $1,583
per person
Jun 6 - Jun 11
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
9.2/10 Wonderful! (494 reviews)
Everything was perfect cant wait to go back

Reviewed on Feb 10, 2026

EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
Price was CA $1,734, price is now CA $1,191 per person
CA $1,191
per person
Jun 6 - Jun 11
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
8.4/10 Very Good! (1,002 reviews)
Customer service walking in was impeccable. Greeted with a smile.

Reviewed on Mar 11, 2026

Anna Maria Island Sun s Up B

Anna Maria Island Sun s Up B

3 out of 5
Price was CA $28,285, price is now CA $20,720 per person
CA $20,720
per person
Jun 6 - Jun 11
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
No reviews
Anna Maria Island Sun s Up A

Anna Maria Island Sun s Up A

2.5 out of 5
Price was CA $28,285, price is now CA $20,720 per person
CA $20,720
per person
Jun 6 - Jun 11
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
No reviews

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 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
The price is CA $279 per night from Apr 12 to Apr 13
CA $279
CA $351 total
Apr 12 - Apr 13
includes taxes & fees
9.4/10 Exceptional! (5,359 reviews)
great spot

Reviewed on Mar 14, 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 $302 per night from Mar 22 to Mar 23
CA $302
CA $341 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,964 reviews)
I had never stayed at a Sparks Hilton before. With the name of Hilton, I would have thought the property would have been in much better condition. The property is old, needs remodeling…. I can’t recommend this hotel.

Reviewed on Mar 15, 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 $505 per night from Apr 11 to Apr 12
CA $505
CA $571 total
Apr 11 - Apr 12
includes taxes & fees
9/10 Wonderful! (73 reviews)
Newly remodeled, great ac, pool was nice. Nice short walk to ocean/beach. Staff only present 9-5pm but did accommodate via text.

Reviewed on Mar 14, 2026

Azul Resort Siesta Key
See all 7,600 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 $769, 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

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

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

Venice Clear Kayak Glass Bottom LED Night Tour

Venice Clear Kayak Glass Bottom LED Night Tour

CA $96
per adult
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.