Pennington Place Vacations from $455

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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 Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
Save 100% on your flight
Price was $766, price is now $455 per person
$455
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,404 reviews)
Good place but wasn’t happy the rooms weren’t cold upon arrival. It took several hours for the ac to cool the room down to a comfortable temperature.

Reviewed on Aug 28, 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
Price was $2,042, price is now $1,073 per person
$1,073
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.8/10 Exceptional! (282 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.

Reviewed on Aug 27, 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $785, price is now $484 per person
$484
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.8/10 Exceptional! (967 reviews)
Property was clean and roomy. Everything we needed was right there. Would definitely return.

Reviewed on Aug 28, 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
Price was $744, price is now $482 per person
$482
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,124 reviews)
Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much.

Reviewed on Aug 16, 2025

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $701, price is now $481 per person
$481
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (878 reviews)
The staff at the restaurant were fantastic!! Staff at the front desk have some opportunity to better facilitate the cart transportation to the Academy. Room carpets. I do not think they were ever vacuumed in all days we were there. Small pieces of paper from our first or second day, were there 3 days later. But, most notoriously, the room smell like sweaty feet, midly, but still. If they have so many athletes around with sweaty shoes, socks and feet, they need to do a better job to vacuum the carpet and avoid keeping all those odors there.

Reviewed on Aug 29, 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
Legacy Trail showing a garden

South Venice

4/5(16 area reviews)

While visiting South Venice, you might make a stop by sights like Venice Area Audubon Society and Jacaranda West Country Club.

Find hotels in South Venice

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
$159 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total with taxes and fees
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
$101 nightly
The price is $114 total per night from Sep 7 to Sep 8
$114 total
Sep 7 - Sep 8
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
Ramada by Wyndham Venice Hotel Venezia

Ramada by Wyndham Venice Hotel Venezia

3.5 out of 5
425 Us Highway 41 Byp N, Venice, FL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $104 total per night from Sep 7 to Sep 8
$104 total
Sep 7 - Sep 8
Total with taxes and fees
Ramada by Wyndham Venice Hotel Venezia
See all 6,934 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
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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

4.5/5(862 reviews)

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
Nice beach to go fossil hunting in Caspersen Beach Florida. #Waterlust #Beach

Caspersen Beach

4.5/5(89 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

4.5/5(6 reviews)

One of southwest Florida’s great fishing spots is this popular attraction in a destination known known as the City on the Gulf..

Venice Fishing Pier

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$55
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

$375
per traveler
100% of travellers recommend
Private Luxury Boat Charter
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.