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.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was CA $1,122, price is now CA $783 per person
CA $783
per person
Jun 28 - Jul 3
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
9/10 Wonderful! (975 reviews)
Very friendly staff great place to stay

Reviewed on Apr 6, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,240, price is now CA $1,548 per person
CA $1,548
per person
Jun 28 - Jul 3
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
9.2/10 Wonderful! (497 reviews)
Loved our stay at the Cottages, intentional and attentive staff, quiet and semi secluded units on a busy island. Rooms were clean, fit the descriptions accurately and had everything we needed. The beach itself makes this the hidden gem. Walking up and down the rest of the beach we began to realize just how special our beach area was. Other beaches were crowded and small, but not Cedar Cove! One other note, our refrigerator was making a grinding noise, we notified management and within an hour they told us they would have a new one delivered and installed. Wow! Thanks and we will be back.

Reviewed on Apr 3, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $1,264, price is now CA $910 per person
CA $910
per person
Jun 1 - Jun 5
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (1,220 reviews)
We were very happy with the location and the newly renovated room. A 2-3 minute walk to the beach. Super clean, close to restaurants, shops, 7 eleven and a small supermarket Staff was very nice and very friendly. Needed a new kurieg after the 1st night and it was replaced with a new one right away

Reviewed on Apr 5, 2026

Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Price was CA $1,457, price is now CA $1,076 per person
CA $1,076
per person
Jun 28 - Jul 3
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
7.4/10 Good! (58 reviews)
Could use another couch in living room not much room to sit. Either than that it was a decent stay.

Reviewed on Oct 22, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Price was CA $2,611, price is now CA $1,933 per person
CA $1,933
per person
May 15 - May 18
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to Sarasota (SRQ)
9.8/10 Exceptional! (327 reviews)
Unit was outstanding. Staff was very friendly. Cannot beat the location and service. Breakfast could use a little more variety. Excellent stay. Planning to return to SK and will stay here again.

Reviewed on Apr 3, 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 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 $282 per night from Apr 12 to Apr 13
CA $282
CA $354 total
Apr 12 - Apr 13
includes taxes & fees
9.4/10 Exceptional! (5,399 reviews)
Very clean, Staff was very friendly and helpful

Reviewed on Apr 8, 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 $203 per night from May 3 to May 4
CA $203
CA $230 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (2,001 reviews)
Rooms are small and pool was dirty There was a bandaide left by the pool the entire time we were there.

Reviewed on Apr 7, 2026

Spark by Hilton Sarasota Siesta Key Gateway
Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
1941 Tamiami Trl Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from May 2 to May 3
CA $110
CA $123 total
May 2 - May 3
includes taxes & fees
7.8/10 Good! (1,011 reviews)
Old, smells

Reviewed on Apr 8, 2026

Days Inn by Wyndham Port Charlotte/Punta Gorda
See all 7,669 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 $783, 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

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

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
100% of travellers recommend
Venice Clear Kayak Glass Bottom LED Night Tour
Sarasota: Siesta Key Clear Kayak Tour with Guide

Sarasota: Siesta Key Clear Kayak Tour with Guide

CA $115
per adult
Sarasota: Siesta Key Clear Kayak Tour with Guide
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.