Pennington Place Vacations from $482

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Your Pennington Place Vacation

Organizing your next getaway just got a lot easier with a vacation package to Pennington Place. Take in everything this neighborhood has to offer while making wonderful memories that will last forever. When it's time to sightsee, you'll find a lot of popular attractions nearby including Sarasota National Golf Course, Legacy Trail and Jacaranda West Country Club. Visit one, two or all during your trip to Pennington Place. Stop daydreaming and start doing. When you're ready to book your ideal vacation to Pennington Place, Expedia will help you get there.

The Latest Pennington Place Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $644, price is now $482 per person
$482
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (2,065 reviews)
The roof top pool was amazing and so fun! Met great people up there!

Reviewed on Mar 13, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,259, price is now $1,380 per person
$1,380
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.2/10 Wonderful! (494 reviews)
Everything was perfect cant wait to go back

Reviewed on Feb 10, 2026

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
South Village
Save 100% on your flight
Price was $1,147, price is now $782 per person
$782
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.4/10 Exceptional! (5,337 reviews)
We had a great stay until someone used the ice machine at 7am. It was directly outside of our bedroom window and they were literally emptying the ice machine. So very noisy. Other than that it was a beautiful property!!! Would stay in a different room definitely!

Reviewed on Mar 11, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was $1,033, price is now $759 per person
$759
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Landing Bradenton Near G.T. Bray Park

Landing Bradenton Near G.T. Bray Park

4 out of 5
Save 100% on your flight
Price was $1,178, price is now $878 per person
$878
per person
Jun 1 - Jun 6
just found
Roundtrip flight included
Minneapolis (MSP) to Sarasota (SRQ)
8.6/10 Excellent! (4 reviews)
Place was lovely Exceeded expectations

Reviewed on Dec 22, 2025

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
$226 nightly
The price is $256 total per night from Apr 12 to Apr 13
$256 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (5,358 reviews)
Good

Reviewed on Mar 13, 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
$220 nightly
The price is $249 total per night from Mar 22 to Mar 23
$249 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (1,958 reviews)
Nice place, friendly staff. Beautiful pool! Breakfast could improve a bit.

Reviewed on Mar 13, 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
$384 nightly
The price is $433 total per night from Apr 11 to Apr 12
$433 total
Apr 11 - Apr 12
Total with taxes and fees
9/10 Wonderful! (69 reviews)
Very comfy and relaxing stay. Staff were awesome

Reviewed on Mar 12, 2026

Azul Resort Siesta Key
See all 7,624 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pennington Place

Venice Beach featuring general coastal views and a sandy beach

Venice Beach

Beachside bliss awaits at a Florida coastal gem where you can swim, fish and hunt for ancient fossils in the sand and beneath the waves.

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
Manasota Beach

Manasota Beach

Why not spend a carefree afternoon at Manasota Beach during your travels in Venice Island? Discover the sunsets while you're in the area.

Manasota Beach

Things to do

Venice Clear Kayak Glass Bottom LED Night Tour

Venice Clear Kayak Glass Bottom LED Night Tour

$70
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.