Cherokee Park vacation rentals
We found 92 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals in Cherokee Park that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Cherokee Park
Showing deals for:Nov 7 - Nov 14
Image gallery for Private Oasis in Sarasota Florida
1010 out of 10 rating
Exceptional
(37 reviews)
Private Oasis in Sarasota Florida
Sarasota, FL
5% off
Price is CA $546
CA $546
CA $5,321 total
CA $5,321 total
includes taxes & fees
Image gallery for Charming Beach Cottage
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Charming Beach Cottage
Sarasota, FL
19% off
Price is CA $167
CA $167
CA $1,661 total
CA $1,661 total
includes taxes & fees
Image gallery for Midcentury Modern 3 BR - With Pool in Sarasota, Close to Beaches!
9.89.8 out of 10 rating
Exceptional
(119 reviews)
Midcentury Modern 3 BR - With Pool in Sarasota, Close to Beaches!
Sarasota, FL
19% off
Price is CA $278
CA $278
CA $3,044 total
CA $3,044 total
includes taxes & fees
Image gallery for Lovely Cottage ❤ Very close to Siesta Beach or Downtown Sarasota!
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Lovely Cottage ❤ Very close to Siesta Beach or Downtown Sarasota!
Sarasota, FL
5% off
Price is CA $156
CA $156
CA $1,693 total
CA $1,693 total
includes taxes & fees
Image gallery for Charming 2br/2ba beach getaway.
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Charming 2br/2ba beach getaway.
Sarasota, FL
5% off
Price is CA $153
CA $153
CA $1,502 total
CA $1,502 total
includes taxes & fees
Image gallery for Pineapples House- POOL private SOUTH facing HOT TUB close to BEACHES- walkable
1010 out of 10 rating
Exceptional
(84 reviews)
Pineapples House- POOL private SOUTH facing HOT TUB close to BEACHES- walkable
Sarasota, FL
20% off
Price is CA $352
CA $352
CA $3,508 total
CA $3,508 total
includes taxes & fees
Image gallery for Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
9.29.2 out of 10 rating
Wonderful
(35 reviews)
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
Sarasota, FL
5% off
Price is CA $156
CA $156
CA $1,693 total
CA $1,693 total
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Cherokee Park
Charming Beach Cottage
Sleeps 7 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Sarasota Renovated Waterfront Home with Dock Wide Open Bay Views Heated Pool
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Historic Laurel Park Home with Retro Guest Cottage
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Amazing Location West of the Trail
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
The Shaded Sanctuary: Enjoy this beautiful home surrounded by some of Florida's
Sleeps 6 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Midcentury Modern 3 BR - With Pool in Sarasota, Close to Beaches!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
119 reviews(119 reviews)
Top rated rentals - Cherokee Park
So private
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
An older charming little place with total privacy and the cutest backyard paradise. We had a wonderful time! So close to town and beautiful beaches too. Definitely coming back
Emma v.
Stayed Mar 2025
Wonderful Place!!
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
We had a wonderful time at Mermaid Cottage. It was clean and welcoming. We had all the amenities we needed and the location was easy to get to every place!! We will be back!!!
Amanda C.
Stayed Aug 2024
Lovely stay
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
We spent every day at the beach, uber was more expensive than expected and transit only ran every hour or so. House was lovely and host was extremely helpful. Beds were VERY comfortable, and short walk to large grocery store.
Christiane T.
Stayed Mar 2024
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Cherokee Park?
In Cherokee Park, both apartments and vacation houses are popular choices for travellers, with several options available in this charming neighbourhood. The apartments typically offer a comfortable living space, fully equipped kitchens, and convenient amenities to ensure a pleasant stay. Many apartments also feature private balconies or patios, great for enjoying the warm Florida weather.
Are there any beach house rentals in Cherokee Park?
In Cherokee Park, Florida, there are several beach house rentals available, primarily appealing to families and groups looking for spacious rooms. These properties typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks where guests can relax and enjoy the warm Florida weather. The location offers convenient access to nearby attractions, including beautiful beaches and local parks, making it an ideal spot for a vacation retreat.
How much does it cost to rent a vacation home in Cherokee Park?
Prices for vacation rentals in Cherokee Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cherokee Park to more spacious homes.
Are there any discounts for Cherokee Park vacation house rentals?
You can find great discounts on house rentals in Cherokee Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Cherokee Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cherokee Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Cherokee Park?
A long-stay vacation rental in Cherokee Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Cherokee Park for a vacation rental?
The best time to visit Cherokee Park for a vacation rental is during the peak season from January to March, with March standing out as the most popular month. This period attracts visitors looking to enjoy the beautiful Florida weather and partake in a variety of outdoor activities. With temperatures typically ranging from the mid to high 20s Celsius, it's an ideal time for beach outings, hiking, or simply relaxing in the sun.
During these months, Cherokee Park comes alive with tourists eager to explore the area's natural beauty, including its scenic trails and lush landscapes. The pleasant climate makes it great for those who enjoy outdoor adventures, whether it's cycling along the park's paths or enjoying a picnic by the lake.
For those seeking a more budget-friendly option, consider visiting in October. This month offers a quieter experience while still allowing you to appreciate the warm weather and beautiful surroundings. Plus, the fall season can bring a unique charm to the park, with fewer crowds and a more tranquil atmosphere.
Are there any remote work vacation rentals in Cherokee Park?
In Cherokee Park, Florida, there are several remote work vacation rentals available, making it a suitable destination for those who need to balance work and leisure. Many properties in the area come equipped with essential amenities such as Wi-Fi and safe environments to ensure a comfortable and productive stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Cherokee Park vacation rental?
Book your Cherokee Park vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Cherokee Park home rental booking on Vrbo?
To find Cherokee Park vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Cherokee Park vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.