Country Oaks Vacations from $378

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Your Country Oaks Vacation

Planning your next escape just got a lot easier with a vacation package to Country Oaks. Immerse yourself in the best this neighborhood has to offer while making wonderful memories along the way. Your trip to Country Oaks wouldn't be complete without exploring popular attractions nearby such as Mall at University Town Center, University Park Country Club and Rolling Green Golf Club. No matter your travel goals or the size of your budget, booking a perfect Country Oaks vacation has never been easier with Expedia.

The Latest Country Oaks Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Save 100% on your flight
Price was $692, price is now $378 per person
$378
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
2/10 (4 reviews)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,295, price is now $657 per person
$657
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.

Reviewed on Nov 24, 2025

Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Save 100% on your flight
Price was $812, price is now $425 per person
$425
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
7.6/10 Good! (4 reviews)
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
Save 100% on your flight
Price was $2,289, price is now $1,248 per person
$1,248
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
Suite 601 is an exceptional ocean front room with views of sunrise and sunset. The room has top notch appliances and was sparkling clean!

Reviewed on Nov 24, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,612, price is now $890 per person
$890
per person
Feb 15 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

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Where to stay in Country Oaks

Find the best Country Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Country Oaks
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South Sarasota

While visiting South Sarasota, you might make a stop by sights like The Landings and Coconuts Family Entertainment Center.

Find hotels in South Sarasota

Country Oaks Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Dec 9 to Dec 10
$85 total
Dec 9 - Dec 10
Total with taxes and fees
9/10 Wonderful! (4,717 reviews)
Yes

Reviewed on Nov 28, 2025

Kompose Boutique Hotel
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
$124 nightly
The price is $140 total per night from Dec 3 to Dec 4
$140 total
Dec 3 - Dec 4
Total with taxes and fees
9.2/10 Wonderful! (5,114 reviews)
Not what I expected, smallish motel like. But nice and clean rooms with good ac and nice kitchenette. Small but cozy little pool. Beach very close. Is good for the price tbh.

Reviewed on Nov 26, 2025

Tropical Beach Resorts
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $192 total per night from Dec 3 to Dec 4
$192 total
Dec 3 - Dec 4
Total with taxes and fees
9.8/10 Exceptional! (2,110 reviews)
Spotless room, courteous staff.

Reviewed on Nov 24, 2025

Carlisle Inn
See all 14,148 properties in Country Oaks
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 Country Oaks

Lido Beach showing general coastal views and a sandy beach

Lido Beach

Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.

Lido Beach
St. Armands Circle featuring a statue or sculpture

St. Armands Circle

Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.

St. Armands Circle
Mall at University Town Center

Mall at University Town Center

You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.

Mall at University Town Center

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$59
per adult
90% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
74% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

$99
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Sarasota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.