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Popular retreat spaces
Explore all of our retreat spaces in Winter Haven. See All ›
Reunion Castle
Serving the Winter Haven, FL area25 guests
Reunion Castle. designed for unforgettable gatherings, celebrations, and creative productions. With its grand architecture, regal interiors, and resort style amenities, this castle inspired retreat is the perfect backdrop for weddings, milestone birthdays, corporate retreats, or high end photo and film shoots.
Inside, you’ll discover soaring ceilings, elegant chandeliers, a
...
From
$222
/hr
2 hr min
Debany Staycation Near Disney
Serving the Winter Haven, FL area15 guests
Debany Staycation Near Disney. Welcome to your ideal creative retreat, off site meeting space, or intimate event venue—nestled in sunny Kissimmee, just minutes from Disney and major attractions.
This 3 bedroom, 2 bathroom home spans ~2,082+ sq. ft. of thoughtfully designed indoor/outdoor space. Inside, enjoy a spacious open concept living and
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From
$175
/hr
3 hr min
The Riverview Estates: Sauna And Pool
Serving the Winter Haven, FL area5.0 (9)
200 guests
The Riverview Estates: Sauna And Pool. Welcome to The Riverview Estates where luxury and entertainment collide in perfect harmony. This stunning property is tailor made to satisfy the most discerning taste, whether you're planning a fabulous gathering with friends, enjoying a short vacation getaway, or even organizing a lifestyle photoshoot for industry
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From
$135
/hr
2 hr min
Sugar Brooke Retreat
Serving the Winter Haven, FL area25 guests
Sugar Brooke Retreat. Sugar Brooke Retreat offers a captivating blend of luxury and tranquility. With its sprawling private, pool view and elegant, contemporary design, this stunning space is perfect for intimate events, private gatherings, and unforgettable celebrations. Whether you're hosting a wedding reception, a corporate retreat, or a creative
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From
$150
/hr
1 hr min
IRE Meetings and Events
Serving the Winter Haven, FL area4.9 (144)
20 guests
IRE Meetings and Events. seat up to 15 people, making it ideal for office meetings, day trading sessions, podcast recordings, CPR training, motivational meetings, team retreats and more. The space features a conference table with 8 Wide Luxury adjustable lumbar chairs, 2 leather couches with seating for 5, and a
...
From
$45
/hr
4 hr min
Veronica Bard Group
Winter Haven, FL5.0 (2)
10 guests
Veronica Bard Group. Step into The Chinoiserie Suite, a beautifully appointed conference room nestled inside a restored historic home in the heart of Winter Haven. This blue and white themed space blends timeless Southern charm with boutique design, creating the perfect setting for your next meeting, strategy session, or
...
From
$50
/hr
2 hr min
Downtown Office Space
Winter Haven, FL2 guests
Professional Desk Space for Rent in a Shared Office – Ideal for Business Professionals
Welcome to our professional and modern office space, perfect for insurance agents, realtors, mortgage brokers, financial advisors, and other business professionals looking for a quiet and productive environment.
🏢 About the Space:
Our office offers
...
From
$10
/hr
5 hr min
Magnolia Farmhouse
Winter Haven, FL12 guests
Step into the world of our meticulously preserved 1928 carpenter's bungalow. This historic gem has witnessed generations of stories unfold within its walls.
Our space greets you with the comfort of 3 bedrooms, two bathrooms, and a versatile office area. During your booking, you'll have access to
...
From
$40
/hr
3 hr min
Lakefront Cottage
Serving the Winter Haven, FL area2 guests
Lakefront Cottage. Tranquil and serene lakefront cottage with huge oak trees for any event setting. Overlooking the lake for picturesque moments. Romantic, quiet, yet unforgettable. Main house has 3 bedrooms and s full bath. Additional outside shower. A separate guest house for additional use. Watch the beautiful sunrise
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From
$150
/hr
2 hr min
My Orlando Vacation Escape
Serving the Winter Haven, FL area20 guests
My Orlando Vacation Escape. families and groups celebrating all of life's wonderful moments such as vacations, weddings, anniversaries, family reunions, golf outings, sports competitions, corporate retreats, etc.
*Amenities*
The house has 12 king beds and 2 kids’ rooms with full over full bunks x 2 per kid room.
First floor bedrooms: White House
...
From
$250
/hr
2 hr min
Luxurious Day Retreat for your employees and meeting - WORK + FUN
Serving the Winter Haven, FL area18 guests
It's a regular 2 story single family 7BR home with 5.5 Bath (3200 Sq ft of space in total). The clubhouse has a lot of amenities a gym, walk in pool, spa, mini golf, lazy river, basketball court and many more.
The home
...
From
$100
/hr
4 hr min
Scuttle Pool Vacation Home
Serving the Winter Haven, FL area14 guests
Scuttle Pool Vacation Home. 🌴 Scuttle Pool Vacation Home – Family Friendly Retreat Near Orlando Attractions
Escape to your Clermont getaway, perfect for families and friends seeking fun, comfort, and relaxation just minutes from Orlando’s world famous attractions. This spacious villa accommodates up to 14 guests across five bedrooms and
...
From
$75
/hr
3 hr min
Beautiful Huge home located in Kissimmee
Serving the Winter Haven, FL area4.8 (9)
16 guests
Discover our spacious Kissimmee Airbnb! This 16 guest house with a pool is perfect for families and friends. It offers multiple bedrooms, a fully equipped kitchen, and a cozy living room close to Walt Disney World and other theme parks. Enjoy the refreshing pool, outdoor seating,
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From
$60
/hr
4 hr min
The Gathering Table Venue
Serving the Winter Haven, FL area5.0 (2)
30 guests
The Gathering Table Venue. Our indoor space is uniquely decorated with a bit of a vintage style. Up to 30 guests can be comfortably seated at our six round tables. The building includes both AC and heat.
Guests could then enjoy games and activities in the large open
...
From
$30
/hr
4 hr min
Amazing Luxury Escape
Serving the Winter Haven, FL area5.0 (2)
250 guests
Nestled amidst the tranquil embrace of nature, this exquisite luxury vacation Mansion offers an unparalleled retreat for those seeking the epitome of relaxation and indulgence. Boasting panoramic views of Lake Toho, the property exudes an aura of serenity and opulence from the moment you arrive. With
...
From
$250
/hr
4 hr min
Bright, Modest Conference Room in Orlando
Serving the Winter Haven, FL area5.0 (10)
8 guests
Our beautiful conference room is perfect for any meeting, workshop or brainstorming session and will surely impress your clients or employees!
Space Features:
WiFi
Large conference table
8 chairs
55" HD TV: HDMI & USB connections to plug in and display
Decorative
...
From
$50
/hr
2 hr min
Grand, Expansive Club Room in Orlando
Serving the Winter Haven, FL area4.7 (39)
30 guests
Our beautiful club room is perfect for any social gathering, celebration or meeting (retreat). Flexible seating allows for casual mingling and dining. A pool table will surely entertain the crowd!
Space Features:
WiFi
Casual seating arrangements: couches, club chairs, tables
Wet bar: mini fridge,
...
From
$165
/hr
3 hr min
Andalusia Mansion
Serving the Winter Haven, FL area4.8 (4)
40 guests
The Mansion is uniquely designed to replicate a Spanish style Mansion in an orange grove and designed garden. The Mansion has a front courtyard with a hand built fountain with Spanish hand painted ceramic tiles, with 4 olive trees and fragrant jasmine and rosemary.
The Mansion
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From
$250
/hr
4 hr min
Comfy Clubhouse in Brandon
Serving the Winter Haven, FL area4.9 (23)
30 guests
Our beautiful clubhouse is perfect for any social gathering, celebration or meeting (retreat). Flexible seating allows for casual mingling and dining. Pool use not permitted.
Space Features:
WiFi
Casual seating arrangements: club chairs, tables
Kitchen: refrigerator, microwave, dishwasher, sink, large countertop, barstools
50"
...
From
$90
/hr
2 hr min
Perfect Private Office
Serving the Winter Haven, FL area5.0 (9)
3 guests
If you are looking to meet with a client or need some peace and quiet alone this is the perfect space for you. The office comes with an executive desk and two guest chairs. Beautiful view of the courtyard will keep your office sunny
...
From
$44
/hr
2 hr min
All-Encompassing Retreat w/ Pool & Game Room!
Serving the Winter Haven, FL area5.0 (7)
20 guests
Memories are waiting to be made at this well appointed 6 bedroom, 3 bathroom Tampa vacation rental. From the game room to the backyard with an above ground pool to the fully equipped kitchen, this single story house is brimming with amenities for all ages and
...
From
$150
/hr
4 hr min
Serene Lakeftont 7 Bedroom Duplex w/ Pool and Hot tub
Serving the Winter Haven, FL area5.0 (3)
25 guests
Fire up the outdoor grill as you watch the sunset over the lake. Enjoy a warm Florida day as you cruise around on lake Jessamine, then take a dip in the pool.
Practice putting on the putting green, enjoy some foosball, or try out the paddle
...
From
$75
/hr
2 hr min
Lakefront Duplex: Boat, Jet Skis, Pool, Hot tub
Serving the Winter Haven, FL area10 guests
Fire up the outdoor grill as you watch the sunset over the lake. Enjoy a warm Florida day as you cruise around on lake Jessamine, then take a dip in the pool.
22 min from Disney
20 min from the convention center and Universal
...
From
$50
/hr
4 hr min
Spacious Lakefront House
Serving the Winter Haven, FL area5.0 (9)
30 guests
Guests have called this place a true “hidden gem.” The view of the sunset over the lake is a welcome surprise in city environments.
Play in the pool, relax in the hot tub, or practice your putts on the putting green.
2 minutes from Camping
...
From
$55
/hr
4 hr min
Roomy meeting room
Serving the Winter Haven, FL area10 guests
A spacious, well lit room with a large rectangular table that can comfortably seat at least ten people. The room is equipped with basic amenities such as chairs and a table. It's perfect for meetings, workshops, or small gatherings. The room is available for daily rental
...
From
$100
/hr
4 hr min
Historic Mediterranean Estate
Serving the Winter Haven, FL area5.0 (27)
50 guests
This 4800 sf historic home was built in 1924 and has been renovated to accommodate all types of guests. Each space tells a story of the house and the furniture has been hand picked to fit the essence of the home.
There is a projector in
...
From
$100
/hr
6 hr min
Cozy, Modern Club Room in Tampa
Serving the Winter Haven, FL area4.7 (11)
30 guests
Our beautiful club room is perfect for any social gathering, celebration or meeting (retreat). Flexible seating allows for casual mingling and dining. A pool table will surely entertain the crowd! Pool use is not permitted.
Space Features:
WiFi
Casual seating arrangements: couch, chairs, tables
...
From
$90
/hr
3 hr min
Cozy Modern Home + Backyard w/ Fire-Pit & Grill
Serving the Winter Haven, FL area4.6 (8)
15 guests
Enjoy a stylish experience at this centrally located home in the heart of Ybor City. Newly renovated, yet historic bungalow, called Casa Gallo named after the famous roosters roaming around the streets.
Casa Gallo features an open floor plan, soaring ceilings, abundant natural light and best of
...
From
$40
/hr
4 hr min
Vibrant, colorful house with gorgeous porch & patio
Serving the Winter Haven, FL area5.0 (4)
85 guests
The bold, eclectic decor and natural light in this spacious home create a fun and welcoming environment for any event! The kitchen, family room, dining room, and breakfast area are well arranged in an open concept for easily gathering together. There's additional seating
...
From
$200
/hr
3 hr min
Oasis in South Seminole Heights
Serving the Winter Haven, FL area5.0 (4)
20 guests
This versatile and convenient space is a unique, peaceful oasis. It serves as an ideal spot for intimate gatherings and retreats. Photographers and videographers seeking a space with a variety of backdrops for headshots and brand shoots will love it.
The indoor living space is
...
From
$125
/hr
3 hr min
Contemporary Conference Room in Tampa
Serving the Winter Haven, FL area5.0 (9)
14 guests
Our beautiful, large conference room is perfect for any meeting, retreat or workshop.
Space Features:
WiFi
Extra large conference table
14 swivel chairs
65" HD TV: HDMI & USB connections to plug in and display
Decorative accent lighting
This space is located in
...
From
$75
/hr
2 hr min
Incredible Lounge & Patio in Orlando
Serving the Winter Haven, FL area4.8 (12)
45 guests
Our beautiful club room is perfect for any social gathering, celebration or meeting (retreat). Flexible seating allows for casual mingling and dining. A foosball table and arcade games will surely entertain the crowd!
Space Features:
WiFi
Casual seating arrangements: couches, club chairs, tables
...
From
$150
/hr
3 hr min
Bear Lake Cottage Retreat
Serving the Winter Haven, FL area20 guests
Bear Lake Cottage Retreat – A Tranquil Lakeside Haven for Creativity and Connection
Welcome to Bear Lake Cottage Retreat, a serene and secluded lakefront escape tucked away in the heart of Central Florida. Surrounded by lush greenery and the soothing sounds of nature, this peaceful sanctuary is
...
From
$100
/hr
3 hr min
S. Tampa Mansion w/ Pool, Nightclub, Meeting Spaces, 22 Person Dining Table
Serving the Winter Haven, FL area5.0 (3)
70 guests
much more! The property features 10 Ensuite Bedrooms. This property is the perfect space for family gatherings, company meetings & retreats, and productions / filming. Private Rentals only Absolutely no Social Events where alcohol is sold, tickets are distributed, attendance is by
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From
$400
/hr
2 hr min
Modern Lounge Area Great for Networking Events
Serving the Winter Haven, FL area5.0 (3)
50 guests
Orlando, FL. Please inquire via Peerspace messaging if you're interested or have any questions.
Features:
•WiFi
•Free Parking
•Kitchen
•Furniture
•Open Layout
•TV's
•Coffee/Water/Tea
•Printer
•Chairs + Tables
Uses:
•Networking Events
•Company Off Sites
•Team Retreats
•Pop Up Shops
•Product Launches
•Business Events
...
From
$150
/hr
3 hr min
Frequently Asked Questions
Pricing and popularity information in this section is based on proprietary Peerspace booking data, reflecting recent booking activity and the latest data available through April 2026.
How popular are retreat spaces in Winter Haven?
Our local hosts have welcomed 2 people into their retreat spaces with reviews averaging 5 stars. 100% of guests said they'd book again.
How much does a retreat space cost to rent in Winter Haven?
Retreat spaces in Winter Haven average $50 per hour to rent, but it’s easy to spend less or more depending on what you’re looking for.
retreat spaces Pricing Range in Winter Haven, FL
Graphic displaying average hourly rates for retreat spaces venues in Winter Haven, ranging between $61.75 and $217.
$50/hr average
How long do people rent retreat spaces in Winter Haven?
Most retreat spaces are scheduled for 9 hours, with 2 people in attendance. You’ll find the most Retreats starting between 8:00 AM and 9:00 AM.
retreat spaces Booking Times in Winter Haven, FL
Image representing average rental time for retreat spaces in Winter Haven, emphasizing most start between 8:00 AM to 9:00 AM.
8:00 AM - 9:00 AM
5:00 AM12:00 PM
Reviews for retreat spaces
Joe A.
Ample House in the heart of Brickell
Jessiana's house was perfect for our team's retreat. Throughout our three days on site, we enjoyed the options for meeting space in different rooms as well as outside on the patio. We also took advantage of the more private spaces for individual Zoom meetings and calls - the extra...
Amanda B.
Quiet, Professional Conference Room in Boca Raton
The space was exactly as advertised. Our board retreat was a big success in the space. The host was very responsive and provided information needed in a timely manner. We will definitely consider holding another meeting in this location. Highly recommend to others looking for a conference room for...
Nicole C.
Luxe Mid-Century inspired Executive Home and Pool
beautiful hidden Oasis. This house was gorgeous for our photo shoot and would make a wonderful space for a retreat. The host was super gracious and easy to communicate with...
Tamika F.
Workshop and Conference room available near to Wynwood
It was a pleasure working with Luisa on this two-day event. The facility was perfect for our retreat and we had more than enough space to do everything we wanted...
Emily F.
The Rustic Retreat
The rustic retreat was perfect for our my best friend’s bridal shower! Its open layout was perfect to fit everyone! Daphne was so easy to work with from beginning to end and super quick to respond. I was also able to rent the major balloon decorations from her so...
Dresden F.
Downtown Conference Room with City View
Hello - We are from Washington D.C. and we had our board retreat in this space. It was so pretty, beautifully, walkable, and SOOOOO much natural light. Technology was easy to figure out and they had everything we needed for sounds and for different computer adjustments. Holly rocked...
Sherry G.
Andalusia Mansion
Here’s a warm and thoughtful review for PeerSpace:
We hosted our women’s retreat at the beautiful Andalucia Mansion (11333 County Rd. 561, Clermont, FL 34711), and it was truly an unforgettable experience. The home is absolutely stunning—set on several acres with picturesque orange groves, offering both privacy...
Shelissa J.
Cal Events Cooper City 🦚 Hidden Gem in Cooper City
This venue is breathtaking! All of my guests were in awe of such a elegant, simple yet impressionable space. I hosted a woman's retreat, and couldn't ask for a better place to give the enchanting, feminine and refreshing vibe that we wanted. Julie is amazing to work with...
Kayla L.
Rustic Home w/ Fabulous Backyard
for a photoshoot and couldn't have asked for a better property. The home was absolutely adorable, the backyard was like a tropical oasis retreat, and everything was very well-kept. Teresa was incredibly responsive and accommodating. I'm already looking for another reason to use her home and would...
Sammy L.
Airy, Boho-Mediterranean Home with Lush Backyard
booked Casa Nomada Retreat for my branding shoot, and it exceeded every single expectation. The space is stunning, beautifully designed, spotless, and filled with perfect natural light. Every corner of the house is aesthetic and photo-ready, which made it an absolute dream for content creation.
The host was wonderful...
Jessica M.
Swanky Unique Large Winter Park Conference / Entertainment Room with Views
Space was great for our office leadership retreat. Any issues were promptly addressed
Steve M.
Swanky Unique Large Winter Park Conference / Entertainment Room with Views
Great host for my staff retreat. I recommend if you have a group of 6 or less
Alicia M.
Warmth Minimalistic Wabi Sabi Country-Style Home
This beautiful space more than met our needs for our team offsite. We wanted a space that would feel cozy, but also stylish and retreat-like. It was perfect for our group of 9! We cooked, we danced, we collaborated, and we had lunch in the beautiful backyard. The rooms...
Jessica M.
Stranahan Boardroom on Las Olas Blvd. with Ocean View
This room was perfect for our firm’s annual retreat. The view is beautiful, we had all the resources we needed available, and the staff was tremendous...
Nancy R.
Rustic lakehouse in Orlando
Krys' Rustic Lakehouse is truly a quaint gem. Our event was unusual as it was a 15 hours wellness retreat. The space met our needs in that it provided a tranquil atmosphere and gorgeous scenery. Krys was accommodating and welcoming. Everyone who participated experienced the warmth of this beautiful lake...
Alwin R.
Plush Modern House Near Wynwood W/ Office & Yard Deck / Jacuzzi
plenty of parking space and a strategic location close to the airport. The neighborhood felt safe, with minimal road traffic, making it a peaceful retreat. Highly recommended...
Christopher S.
Spacious Historic Renovated Spanish Style Home
Great space for hosting a dinner, meeting or get together with family/friends or a small company retreat. Easy access and very clean. Will book again...
Similar searches in Winter Haven, FL
Updated March 19, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.