Pennington Place Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Jul 29 - Aug 5

    The Perry Hotel Naples + Flight

    Naples
    7 nights
    4.5 star property
    9.4/10 - Exceptional (825 reviews)
    "Nice stay at North Naples, liked the rooftop bar"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • 1 stop RSW - YYZ • 1 stop
    CA $1,627
    CA $973
    per traveller
    found 1 day ago
    The Perry Hotel Naples
  • View from room
    Jul 18 - Jul 25

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    7 nights
    4.5 star property
    9.0/10 - Wonderful (1,008 reviews)
    "First time staying at Hotel La Playa, and honestly, we loved it. I went with my husband and my adult son, and the experience exceeded our expectations.The location is amazing, and the attention and service from the entire staff were spectacular from the moment we arrived. Everything was spotless: the rooms, the common areas, and the beach. The food was delicious, the views were beautiful, and the atmosphere was perfect for relaxing and enjoying time with family. It truly feels worth every dollar..."
    Reviewed May 26, 2026
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $3,683
    CA $2,036
    per traveller
    found 6 hours ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 12 - Aug 20

    Hyatt Vacation Club at Coconut Cove, Bonita Springs + Flight

    Bonita Springs
    8 nights
    4.0 star property
    9.0/10 - Wonderful (886 reviews)
    "Xx"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - MIA • Nonstop MIA - YUL • Nonstop
    CA $2,058
    CA $1,350
    per traveller
    found 5 hours ago
    Hyatt Vacation Club at Coconut Cove, Bonita Springs
  • Exterior
    Jun 28 - Jul 11

    Chadwick Cove Resort & Marina + Flight

    Manasota Key
    13 nights
    4.0 star property
    9.6/10 - Exceptional (19 reviews)
    "The listing stated step to beach. It was not only across the street but offered no access. "
    Reviewed May 10, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $2,149
    CA $1,430
    per traveller
    found 1 day ago
    Chadwick Cove Resort & Marina
  • Exterior
    Jul 18 - Jul 25

    Shell Island Beach Club + Flight

    East End
    7 nights
    4.0 star property
    9.6/10 - Exceptional (23 reviews)
    "Very clean. Excellent location, close to beach, walkable to restaurants."
    Reviewed December 21, 2025
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $2,999
    CA $2,019
    per traveller
    found 6 hours ago
    Shell Island Beach Club

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

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

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 14 to Jun 15
CA $198
CA $224 total
Jun 14 - Jun 15
includes taxes & fees
8.4/10 Very Good! (2,118 reviews)
"The pool was perfect, room was clean, breakfast was lovely. Very nice stay!"

Reviewed on May 26, 2026

Spark by Hilton Sarasota Siesta Key Gateway
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
The price is CA $272 per night from May 31 to Jun 1
CA $272
CA $343 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (5,511 reviews)
"Great location, just steps from the beach"

Reviewed on May 26, 2026

Tropical Beach Resorts
Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG

2.5 out of 5
5730 Gantt Road Sarasota FL
Fully refundable
The price is CA $145 per night from Jun 2 to Jun 3
CA $145
CA $164 total
Jun 2 - Jun 3
includes taxes & fees
8/10 Very Good! (1,012 reviews)
"Staff was great, facilities were very nice and clean, parking was good, breakfast was good and the location was perfect."

Reviewed on May 26, 2026

Holiday Inn Express Sarasota East - I-75 by IHG
See all 7,721 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 , 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)

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

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
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.