Best Vacation Homes in Cherry Pocket
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $325/Night
7 Nights - US $2,276
House
9.0(21 Reviews)
4 Bedrooms
1 Bath
6 Guests
1539.24 ft²
Oceanfront- Fireplace/Heating
Pool
Ocean View
US $160/Night
7 Nights - US $1,118
House
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Pet Friendly- Kitchen
US $316/Night
7 Nights - US $2,212
House
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Child Friendly
US $412/Night
7 Nights - US $2,881
House
5 Bedrooms
3 Baths
10 Guests
1496.18 ft²
Hot Tub- Balcony/Terrace
Breakfast- Parking
US $5,280/Night
7 Nights - US $36,960
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $277/Night
7 Nights - US $1,941
House
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $244/Night
7 Nights - US $1,709
Villa
9.6(89 Reviews)
3 Bedrooms
2 Baths
6 Guests
Private Pool- Fireplace/Heating
- Pool
- Ocean View
US $138/Night
7 Nights - US $967
Cherry Pocket Luxury Rentals
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $296/Night
7 Nights - US $2,070
House
5 Bedrooms
3 Baths
10 Guests
2700 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $238/Night
7 Nights - US $1,665
House
9.0(4 Reviews)
3 Bedrooms
2 Baths
5 Guests
960 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $181/Night
7 Nights - US $1,270
Villa
9.0(72 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $175/Night
7 Nights - US $1,224
House
3 Bedrooms
3 Baths
6 Guests
1496 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $5,652/Night
7 Nights - US $39,566
House
5 Bedrooms
3 Baths
10 Guests
2700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $679/Night
7 Nights - US $4,751
House
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $293/Night
7 Nights - US $2,050
House
3 Bedrooms
1 Bath
6 Guests
- Pet Friendly
- Child Friendly
Security/Safety
US $286/Night
7 Nights - US $2,005
Cherry Pocket Pet Friendly Vacation Rentals
Cabin
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,232
Cabin
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,083
Cabin
9.8(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Balcony/Terrace
View- Pet Friendly
- Kitchen
US $195/Night
7 Nights - US $1,365
Cabin
8.8(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $176/Night
7 Nights - US $1,232
House
8.2(16 Reviews)
2 Bedrooms
2 Baths
12 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $161/Night
7 Nights - US $1,126
House
2 Bedrooms
2 Baths
13 Guests
1478 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $152/Night
7 Nights - US $1,065
House
5.0(1 Review)
3 Bedrooms
1 Bath
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $250/Night
7 Nights - US $1,750
House
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $267/Night
7 Nights - US $1,871
Cherry Pocket Large Vacation Homes
House
10.0(51 Reviews)
4 Bedrooms
3 Baths
16 Guests
2000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $286/Night
7 Nights - US $1,999
House
6.0(1 Review)
6 Bedrooms
4 Baths
11 Guests
3000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $256/Night
7 Nights - US $1,791
Why Choose Rent By Owner for your Cherry Pocket Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Cherry Pocket
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit for your stay in this charming area can enhance your experience, as the region offers different attractions and weather patterns throughout the year that can perfectly suit your vacation plans.
Peak Season Highlights
March to May (Spring)
During spring, the area's pleasant weather makes it an ideal time to explore outdoor activities and enjoy your stay in this charming destination.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
November to February (Winter)
Winter offers cooler temperatures and fewer crowds, providing a peaceful setting for relaxation and exploring at your own pace.
Average Temperature Daytime: 65°F - 75°F - Nighttime: 45°F - 55°F
Off-Season Highlights
June to August (Summer)
Summer months see higher temperatures and humidity, perfect for those who enjoy hot weather and are looking for budget-friendly options.
Average Temperature Daytime: 85°F - 95°F - Nighttime: 70°F - 80°F
September to October (Fall)
Autumn brings milder weather and fewer visitors, making it an excellent time for tranquil retreats and enjoying the natural scenery.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
Weekly Weather Forecast for Cherry Pocket
How to Book Your Cherry Pocket 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 Cherry Pocket
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 or patios where you can relax and take in the scenic views of the region.
- Take advantage of private or shared swimming pools typically available at properties in this destination.
- Make use of outdoor grills or barbecue stations for preparing meals while enjoying the pleasant climate.
- Benefit from spacious yards or gardens perfect for outdoor games or leisurely walks around the property.
- Discover nearby lakes or waterfront access for kayaking, paddleboarding, or fishing activities.
- Utilize covered porches or verandas to unwind outdoors regardless of the weather conditions.
- Explore landscaped pathways or walking trails often located within or near the vacation rental grounds.
Top Attractions Around Cherry Pocket
What attractions are nearby?
During your stay here, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and charm of the region surrounding Cherry Pocket, Lake Wales, Florida.
Family Activities
- Lake Wales Scenic Boat Tour: Embark on a relaxing boat tour around the picturesque lakes in this area to enjoy the natural beauty and wildlife that make this destination unique.
- Cherry Pocket Paddleboarding: Try your hand at paddleboarding on the calm waters nearby, offering a fun and family-friendly way to explore the region’s scenic shoreline.
- Visit Bok Tower Gardens: Explore the lush gardens and historic tower, providing a peaceful environment perfect for family outings and picnics in the region.
- Wildlife Viewing at Lake Kissimmee State Park: Discover local fauna and enjoy outdoor activities such as bird watching and nature walks in this nearby state park, ideal for an adventurous family day.
Adult Activities
- Fishing at Lake Wailes: Enjoy a relaxing day casting your line in one of the area's popular fishing spots, perfect for unwinding during your stay.
- Exploring Bok Tower Gardens: Discover the lush gardens and historic tower in nearby Lake Wales, offering tranquil walks and exquisite scenery for nature enthusiasts.
- Boating on Crooked Lake: Experience the serenity of the region by renting a boat and exploring Crooked Lake’s calm waters, ideal for aquatic adventures.
- Golfing at Lake Wales Country Club: Play a round of golf on the scenic courses designed for both casual players and enthusiasts seeking a challenging game.
Cherry Pocket Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature Spots: Take advantage of the area's natural beauty by visiting nearby parks and lakes to enjoy outdoor activities like kayaking, fishing, or scenic walks.
- Plan Early for Popular Times: Secure your preferred vacation rentals during peak seasons well in advance to ensure a comfortable and stress-free stay here.
- Discover Authentic Dining Experiences: Sample local cuisine at nearby eateries to fully immerse yourself in the region’s culinary offerings and culture.
- Utilize Nearby Amenities: Make the most of the available facilities around your accommodation, such as boat rentals or recreational centers, to enhance your visit here.
Transportation Options
- Personal Vehicle: Renting or using your own car gives you the flexibility to explore this area and visit nearby attractions at your own pace.
- Taxi Services: Local taxi services provide convenient transportation options for quick trips or when you prefer not to drive in this region.
- Rideshare Apps: Rideshare platforms like Uber and Lyft operate here, offering a reliable and hassle-free way to move around this destination.
- Public Transportation: Bus services available locally connect you to key points within the region, making it easier to access your vacation rentals and nearby sites.
Local Customs Options
- Southern Hospitality: You’ll notice a warm welcome and friendly interactions that reflect the region’s famous Southern hospitality during your stay here.
Engaging in local fishing customs, which are popular in the area, gives you an authentic experience surrounded by scenic lakes and tranquil waters. - Community Events: Participating in neighborhood gatherings and seasonal festivals provides insight into the area's close-knit community spirit.
- Local Cuisine Etiquette: Savor regional specialties with a respectful appreciation for traditional dining customs that highlight Florida’s culinary flavor.
Cherry Pocket Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Cherry Pocket?
There are a lot of options in Cherry Pocket. If you plan on staying in the Cherry Pocket area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cherry Pocket:
- Premium Lake Wales Getaway!
- Beautiful holiday home with private swimming pool suitable for 6 people
- Luxury Villa, with opt. heated, private pool near Legoland/Disney/Orlando
- Villa met prive zwembad nabij Orlando optional heated pool
- Cozy & Inviting 3BR and 2 Bath Full Kitchen + Laundry
- Welcome to Casa Tallman - Your Exclusive 3-Acre Private Retreat
- Hidden Gem - Hot Tub/ Fire Pit/ Hammock/ Grill Area
- Charming 3-bedroom house with AC in peaceful neighborhood, minutes from Disney!
- Charming 2-bedroom house in Haines City with AC, WiFi
- Charming house in beautiful Haines City with AC, WiFi
2. Which vacation homes in Cherry Pocket are best for families?
If you are looking for a family-friendly vacation home in Cherry Pocket, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cherry Pocket:
3. How many Rentbyowner vacation rentals are available in Cherry Pocket?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 28 in the Cherry Pocket 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 Cherry Pocket.
4. What is the cancellation policy for vacation rentals in Lake Wales, Florida?
The cancellation policy varies depending on the specific listing you choose. It is recommended to review the cancellation details directly on the property’s page or contact the owner for precise information.
5. How do I confirm the availability of a rental property in the region?
Availability is subject to change and can be checked by selecting your desired dates on the listing. For real-time updates, reach out to the property owner or check the booking calendar.
6. Are there any specific rules or regulations I should be aware of when staying at a vacation rental here?
Each property has its own set of house rules and regulations, which are typically outlined on the listing. It’s advisable to read these carefully or contact the owner if you have any questions.
7. What amenities are usually included with vacation rentals in this area?
Amenities vary between listings but often include essentials like Wi-Fi, parking, and kitchen facilities. To ensure the property meets your needs, verify the available amenities on the individual property page.
8. Is it possible to get personalized assistance or special requests when booking a rental in Lake Wales, Florida?
Yes, many owners are willing to accommodate special requests or provide personalized assistance. Contact the property owner directly through the listing to discuss your specific needs before booking.
