Discover Your Perfect Cherokee Park Vacation Homes

Best Vacation Homes in Cherokee Park

See More Cherokee Park Vacation Rentals

Cherokee Park Pet Friendly Vacation Rentals

|
10.0 (183 Reviews)
Cottage
The Inn On Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Cherokee Park on PetFriendly.io

Cherokee Park Large Vacation Homes

|
10.0 (4 Reviews)
Villa
Lido Beach Villa
  • Air Conditioner
  • Parking
  • Pool
View Availability
See More Family Vacation Rentals in Cherokee Park on FVR

Why Choose Rent By Owner for your Cherokee Park Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Cherokee Park Vacation Rentals

Where are the best neighborhoods to stay in Cherokee Park?

When choosing a neighborhood to stay in within Cherokee Park, Sarasota, Florida, you’ll find a peaceful and inviting atmosphere that offers both comfort and convenience. This charming area provides easy access to local attractions while maintaining a relaxed environment ideal for your getaway. Whether you’re seeking proximity to natural beauty or looking for a quiet place to unwind, the neighborhoods here are perfect for discovering the best of Sarasota’s coastal appeal. Enjoy a seamless booking experience with dependable vacation rentals that cater to your specific preferences, ensuring your stay in Cherokee Park is both enjoyable and memorable.

Bayview

This neighborhood offers a peaceful setting with beautiful views, making it an ideal choice for those seeking relaxation. You’ll find that staying here provides convenient access to local attractions while enjoying the serene atmosphere of Sarasota’s waterfront.

View 4211+ Rentals in Bayview

Shoreland Woods

Known for its lush landscapes and quiet streets, Shoreland Woods is perfect if you want a calm, residential area within reach of the region’s vibrant amenities. Here, you can experience the tranquility of Sarasota while remaining close to popular dining and shopping options.

View 5844+ Rentals in Shoreland Woods

South Poinsettia

This lively neighborhood features easy access to the region's cultural and recreational spots, making it a great base for exploring Sarasota’s diverse attractions. Staying in South Poinsettia ensures you are near essential amenities, offering both comfort and convenience during your visit.

View 5334+ Rentals in South Poinsettia

Best Times to Visit Cherokee Park

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you enjoy the best weather and local events, making your stay in this vibrant destination truly memorable.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, the area experiences its peak season as visitors seek warm-weather escapes in Sarasota, Florida. This is a popular time for enjoying outdoor activities and local events.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 50°F to 55°F
spring
Spring (March to May)

Spring attracts travelers looking to enjoy pleasant temperatures and blooming scenery, making it an ideal period for exploring the region’s natural beauty and outdoor attractions.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Off-Season Highlights

image
Summer (June to August)

The summer months see fewer visitors due to the hotter and more humid weather, providing a quieter retreat for those seeking tranquility and lower rates on vacation rentals.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
image
Fall (September to November)

Early fall can be less crowded, offering peaceful surroundings and comfortable weather for exploring the area’s scenic landscapes before the winter rush begins.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 60°F to 65°F

Weekly Weather Forecast for Cherokee Park

How to Book Your Cherokee Park Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Cherokee Park

More Top-Rated Vacation Rentals in Cherokee Park Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor seating areas such as patios or decks to relax and take in the surrounding scenery.
  • Benefit from spacious yards or gardens perfect for outdoor activities or a quiet retreat.
  • Make use of private or shared swimming pools for a refreshing escape during warm days.
  • Take advantage of barbecue grills for outdoor cooking experiences with family and friends.
  • Explore well-maintained walking paths or trails directly accessible from the property.
  • Utilize outdoor dining spaces ideal for enjoying meals al fresco in this inviting area.
  • Access to lakes, ponds, or nearby waterways for fishing, kayaking, and other water-based activities.

Top Attractions Around Cherokee Park

What attractions are nearby?

While staying in this charming area, you can enjoy a variety of outdoor activities nearby, including scenic walking trails, birdwatching opportunities, and peaceful picnicking spots that highlight the natural beauty of Sarasota’s most beloved outdoor spaces.

image
image

Family Activities

  • Exploring the Trails: You can enjoy family-friendly walking and biking trails that weave through the lush greenery, providing a perfect outdoor adventure for all ages in this scenic area.
  • Picnicking by the Lake: The tranquil lakeside spots are ideal for setting up a family picnic, allowing you to relax and soak in the natural beauty of this popular destination.
  • Wildlife Observation: With plenty of birdwatching opportunities, your family can experience the region's diverse wildlife while engaging with nature in its natural habitat.
  • Playground Fun: The well-maintained playgrounds offer safe, fun activities for children to enjoy after exploring the surrounding areas.
image

Adult Activities

  • Bird Watching Tours: Engage in guided bird watching experiences that allow you to observe the region's diverse avian species in their natural habitat.
  • Nature Trails and Hiking: Explore scenic walking paths through lush landscapes, perfect for enjoying the tranquil beauty of this destination while staying active.
  • Fishing Excursions: Try your hand at freshwater fishing in local lakes and ponds, offering a relaxing way to connect with the outdoors here.
  • Paddle Boat Rentals: Discover the calm waters by renting a paddle boat, an enjoyable activity that provides a unique perspective of the area's natural surroundings.

Cherokee Park Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Trails: Take advantage of the scenic pathways in the area to enjoy outdoor activities and discover hidden natural beauty around your vacation rental.
  • Visit Nearby Beaches: Plan your days around the pristine shoreline just a short drive away, perfect for relaxing or engaging in water sports during your stay.
  • Experience Local Cuisine: Savor authentic flavors at local eateries, providing a taste of regional cuisine that complements your stay here.
  • Plan Off-Peak Visits: Visit popular spots during quieter hours to avoid crowds and enjoy a more relaxed atmosphere during your vacation in this destination.

Transportation Options

  • Florida Gulf Coast Trolley: This eco-friendly trolley system makes exploring the area around your Sarasota vacation rentals convenient and effortless.
  • Rental Cars: Renting a car provides the flexibility to visit scenic spots and local attractions in the region at your own pace.
  • Public Transit - SCAT Bus Service: The Sarasota County Area Transit (SCAT) offers reliable bus routes that connect you to key locations within the area.
  • Taxi and Rideshare Services: Taxis and popular ridesharing options are readily available here, offering quick and comfortable transportation around the region.

Local Customs Options

  • Local Seafood Cuisine: Embrace the region's rich fishing heritage by trying fresh seafood dishes that are a staple here.
  • Festival Celebrations: Participating in seasonal festivals offers a glimpse into the area's vibrant community spirit and cultural traditions.
  • Beach Etiquette: Respectful behavior on the sandy shores ensures a pleasant experience for all visitors enjoying the coastal environment.
  • Environmental Conservation: Engaging in eco-friendly practices helps preserve the natural beauty that attracts travelers to this destination.

Frequently Asked Questions About Cherokee Park?

1. What are the top vacation rentals in Cherokee Park?

There are a lot of options in Cherokee Park. If you plan on staying in the Cherokee Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cherokee Park:

2. How many vacation rentals have private pools in Cherokee Park?

There are 1057 vacation rentals with private pools near Cherokee Park. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cherokee Park are best for families?

If you are looking for a family-friendly vacation home in Cherokee Park, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cherokee Park:

4. How many Rentbyowner vacation rentals are available in Cherokee Park?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 4796 in the Cherokee Park area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cherokee Park. 

5. What is the cancellation policy for vacation rentals in Sarasota, Florida?

The cancellation policy varies depending on the individual property listing. It’s important to review the specific policy details provided in the rental listing or contact the property owner directly to understand the terms and any associated fees.

6. How do I find the best vacation rental deals in the area?

To secure the best deals in Sarasota, Florida, consider filtering listings by price, amenities, and reviews. Contacting property owners directly can also provide insights into any special offers or discounts available for your travel dates.

7. Are there any house rules or restrictions I should be aware of before booking?

Yes, each vacation rental has specific house rules which are outlined in the listing. Be sure to read these rules carefully and reach out to the host if you have any questions or need clarification about restrictions pertaining to the property.

8. What amenities should I expect from vacation rentals here?

Most properties in Sarasota, Florida, offer a range of amenities including Wi-Fi, air conditioning, kitchen facilities, and outdoor spaces. For detailed information on what each rental provides, consult the listing description or contact the host directly.

9. How can I ensure my stay aligns with local regulations and safety standards?

It’s advisable to review the listing for compliance with local regulations and safety features. You can also contact the property owner for confirmation that the rental adheres to safety standards and regulations in the Sarasota area.

Cherokee Park Top Rated Vacation Rentals

|
10.0 (2014 Reviews)
Hotel
Carlisle Inn
  • Air Conditioner
  • Parking
  • Pool
View Availability
See More Cherokee Park Vacation Rentals