Commercial Real Estate in Winter Haven available for sale
Winter Haven Airbnb Properties For Sale

Airbnb Properties for Sale within 50 kilometers of Winter Haven, FL, USA

More details for 555 E Stanford St, Bartow, FL - Flex for Sale

Historic Bartow - 3 Buildings Comm / Resid - 555 E Stanford St

Bartow, FL 33830

  • Airbnb Property
  • Flex for Sale
  • $1,697,500 CAD
  • 8,914 SF
  • Air Conditioning

Bartow Flex for Sale - Polk County

PLEASE SEE ATTACHED BROCHURE FOR MORE DETAILS AND THE WEBSITE LINK FOR EXTRA PHOTOS AND VIDEO. Stunning Victorian-style home built in 1906 and formerly operated as a Bed & Breakfast and Tea House.. Also known as the "My Girl" house, and lately as Hope House, the main portion of the property offers approximately 5,776 SF under air. The property blends historic charm with extensive renovations, while preserving its original character. Zoned R-3, City of Bartow. The uses go well beyond just residential and include some of the following commercial uses: Airbnb, traditional bed and breakfast or guesthouse, group home, family care home, hospice, rehab etc. Professional office uses are also possible. The tour of the property starts with a stunning wrap around, 1,500 SF porch, a perfect setting for gatherings, meetings or events, or a place for morning coffee. The grand foyer opens to multiple living spaces including a front sitting room, formal living and dining rooms, private office, and a spacious updated kitchen with modern cabinetry, appliances, counter bar, and separate dining area. The first floor also features a large primary suite with fireplace and ensuite bath. Please see attached property brochure for more details, and website link for video and all photos. Upstairs includes a gorgeous loft/flex space and five additional bedrooms, each with its own character, fireplace and ensuite bathroom — ideal for bnb, group home, or multi-generational living. Additional improvements include a 1,000 SF two-story guest house (built 2022) with 1 bedroom, 1 bath and loft and a 500 SF air-conditioned flex building (ideal for office, gym, or media room). There is a large pool on the property, as well as 7 fireplaces, wainscoting, crown moulding, some original wood floors, transom windows and french doors. This property is a must see! ** Some photos in the guesthouse (only) are virtually staged. **

Contact:

Saunders Real Estate

Date on Market:

2026-03-12
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More details for Turnkey Short-Term Rental Business – Flex for Sale, Kissimmee, FL

Turnkey Short-Term Rental Business

  • Airbnb Property
  • Multifamily for Sale
  • $2,281,440 CAD
  • 4,526 SF
  • 2 Multifamily Properties

Kissimmee Portfolio of properties for Sale - Osceola Outlying

This listing represents a fully turnkey and automated Short-Term Rental (STR) business operating in the high-demand Disney Corridor of Central Florida. The sale includes three income-producing properties, a complete digital ecosystem, an established brand, and all operational infrastructure necessary for remote ownership. The business demonstrates consistent multi-year performance. One property was added mid-2023, followed by a fully stabilized year in 2024 and normalized operations in 2025. On a blended three-year basis, the portfolio generates approximately $120,000 in stabilized annual net operating income. Offered as a going-concern investment, this opportunity is ideal for passive or out-of-state investors seeking immediate cash flow in a proven Florida STR market without startup or ramp-up risk. The business operates under Margarita Vacation Rentals, a recognized name with a strong online presence, including a full website and domain (MargaritaVacationRentals.com), Airbnb Superhost status, VRBO Premier Host status, and optimized listings on multiple booking platforms. Each property is fully furnished, professionally staged, and located in two top-performing resort communities—Windsor at Westside and Regal Palms—offering premium amenities such as lazy rivers, pools, clubhouses, gyms, security, and guest services. The business is engineered for low-touch, remote management. It runs on an automation system that handles guest messaging, vendor notifications, cleaning schedules, HOA compliance alerts, price optimization, and calendar syncing across Airbnb, VRBO, and Booking.com. Cleaning teams, pool service providers, and maintenance vendors are already in place and familiar with the operation. This is not just a real estate sale—it is the acquisition of a fully automated short-term rental business with approximately $194K in average annual gross revenue and $120K in stabilized annual net operating income based on multi-year performance. The business is ideal for investors seeking passive cash flow, out-of-state buyers, or those looking to expand into the STR space with a fully established and profitable platform.

Contact:

Margarita Vacation Rentals

Property Subtype:

Multi Family

Date on Market:

2025-12-11
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More details for 2250 N Hoagland Blvd, Kissimmee, FL - Multifamily for Sale

Villa Del Sol-Kissimmee Condos - 2250 N Hoagland Blvd

Kissimmee, FL 34741

  • Airbnb Property
  • Multifamily for Sale
  • $6,111,000 CAD
  • 395,750 SF
  • Air Conditioning
  • 24 Hour Access
  • Kitchen
  • Pool
  • Smoke Detector

Kissimmee Multifamily for Sale

Visit our website: TheAptBrokers.com for detailed financials and offering memorandums for both portfolios. The Apartment Brokers proudly present two stabilized condominium portfolios in Kissimmee, Florida the Bella Vista Condos (12 units) and the Villa del Sol Condos (12 units). Offered together or separately, these 24 units provide investors with a rare opportunity to acquire income-producing assets in one of Central Florida’s most dynamic rental markets. Both portfolios are located just 8–10 miles (approximately 15 minutes) from Walt Disney World Resort, positioning them to capture strong and consistent rental demand. The close proximity to the tourism corridor supports steady occupancy from the large local workforce in hospitality, tourism, and service industries, while also offering the potential for short-term rental strategies that can drive higher returns.

Contact:

The APT Brokers.com

Property Subtype:

Apartment

Date on Market:

2025-10-01
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More details for 1002 Park Club Dr, Kissimmee, FL - Multifamily for Sale

7 Townhomes Units Fully Furnished - 1002 Park Club Dr

Kissimmee, FL 34746

  • Airbnb Property
  • Multifamily for Sale
  • $2,376,500 CAD
  • 9,037 SF
  • Fitness Center
  • Kitchen
  • Pool

Kissimmee Multifamily for Sale

7 Townhome units with 3 bedroom, 2.5 bathrooms that comes Fully Furnished and TURNKEY Townhomes located in Orlando/ Kissimmee MSA. These properties are perfectly suited for short-term rentals, Airbnb or as a primary home with a host of desirable amenities. Upon entering, you'll be greeted by a spacious and inviting living areas that provides ample space for relaxation and entertainment. The open floor plan seamlessly connects the kitchen, dining area and living room, creating a perfect space for family gatherings or hosting guests. All the bedrooms rooms are are in the second floor with the master bedroom with it’s own balcony. This community features the following amenities- 2 clubhouse, 2 pools, fitness center, lake access, gazebo, covered playground, basketball, tennis and volleyball courts. HOA includes 24 hours security guard, gated community, clubhouse amenities, garbage collection, irrigation and landscaping services. Easy access to shopping centers, restaurants, schools, and major theme parks. Kissimmee's vibrant atmosphere and proximity to Orlando's renowned attractions make it a highly desirable place to invest. Seller Financing available.

Contact:

Brokers Real Estate Group, Inc

Property Subtype:

Apartment

Date on Market:

2023-09-01
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More details for 921 Paradise Dr, Davenport, FL - Multifamily for Sale

Windsor Island Resort Townhome - 921 Paradise Dr

Davenport, FL 33897

  • Airbnb Property
  • Multifamily for Sale
  • $611,100 CAD
  • 2,283 SF

Davenport Multifamily for Sale - Polk County

Turnkey 5-bedroom, 4.5-bath townhome in the highly sought-after Windsor Island Resort — one of Central Florida’s top-performing short-term rental destinations. This property offers 2,283 square feet of luxury living with an open-concept layout, private screened pool, and dual primary suites for maximum guest comfort. The home has never been in a rental program and is in excellent condition — fully ready to be launched as a short-term rental or used as a private vacation home. Investors can benefit from immediate setup flexibility, choosing their own management company, furnishing package, and pricing strategy without any existing commitments. Located just steps from the resort clubhouse, lazy river, tiki bar, fitness center, and mini golf, this property offers everything guests look for in a high-demand vacation rental community. ?? Highlights: 5 Bedrooms / 4.5 Baths / 2,283 Sq Ft Private screened pool + lanai Dual primary suites (upstairs and downstairs) Resort amenities: clubhouse, lazy river, splash pad, arcade, sports courts, on-site dining Zoned for short-term rental (STR) Not currently enrolled in a rental program — ready for immediate activation ?? Location: Minutes from Disney, major attractions, restaurants, and shopping — this property sits in one of Orlando’s most desirable short-term rental zones, making it an ideal investment or personal retreat. A detailed financial analysis projects healthy returns across multiple occupancy levels. The home is not currently enrolled in a rental program, providing full flexibility for investors to self-manage or select their preferred property management partner. ?? Pro Forma Summary (Estimated Performance): Average Daily Rate (ADR): $235 – $265 Occupancy Scenarios: Conservative (55%): NOI ˜ $19,588 | Cap Rate 3.6% Moderate (70%): NOI ˜ $33,100 | Cap Rate 6.0% High (85%): NOI ˜ $48,120 | Cap Rate 8.7% Total Revenue Range: $51,235 – $88,150 annually Operating Expenses Include: Property management (20%) Utilities (electric, water, internet, cable) HOA / resort fees Property taxes, insurance, and maintenance ?? Highlights: Turnkey short-term rental investment opportunity Not currently in a rental program — ready for immediate activation Located in one of Central Florida’s top-performing STR communities Resort amenities include clubhouse, lazy river, tiki bar, arcade, and sports courts Minutes to Disney and major Orlando attractions

Contact:

PrimeFit Properties LLC

Property Subtype:

Apartment

Date on Market:

2025-10-19
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More details for 701 Keen Rd. – Multifamily for Sale, Frostproof, FL

701 Keen Rd.

  • Airbnb Property
  • Multifamily for Sale
  • $1,935,149 CAD
  • 7,501 SF
  • 3 Multifamily Properties

Frostproof Portfolio of properties for Sale - Polk County

Here’s the opportunity you’ve been waiting for, a rare multi-unit income producing property! There are 8 units total, currently being rented out on a month-to-month basis. The property is nestled on nearly 4 acres under a canopy of old Florida charm, this one-of-a-kind property features a 3bd/2ba main residence, 4 architecturally charming A-frame 2bd/2ba cottages, and a multi unit apartment building with two units that are 1bd/1ba and one unit that’s a 2bd/1ba. All grandfathered under ARR zoning. The grounds are thoughtfully designed to offer both privacy and community, including a screened–in saltwater pool (new pump and recently resurfaced), garden pathways, shaded gathering areas, and plenty of parking. Just a stones throw away from the public boat ramp to crooked lake, where your guests or tenants can enjoy year round, boating, kayaking, and world class fishing. There’s also an Internet tower for fast Internet, property wide water softener system, a Generac generator for the apartment building, two large sheds, 6 smaller storage sheds, large chicken coop with run, fruit trees including mango, starfruit, cherry, lemon, lychee, pomegranate, banana, and numerous other young fruit trees. The main home was built in 2015 has a metal roof, carport, two open porches, and comes furnished including washer and dryer. All 4 A-frame cottages have new metal roofs as of April 2025 and all new HVAC systems. The 2/1 apartment also has a huge bonus room with a loft and a private laundry room (which could be turned into a 4th unit). But that’s not all there’s also a RV 30 amp hook up (with ample space for up to 9+ more) envisioning the potential for 10+ oversized RV pads, this property combines existing cash flow with development upside potential. This property is not just a residence or average income producer – it’s a flexible income–generating resort with limitless potential:think short-term vacation rentals, wellness retreats, church camps, rehabilitation centers, RV expansion, corporate rentals, live + earn model, or multigenerational living.

Contact:

Keller Williams Realty Smart Realty

Property Subtype:

Multi Family

Date on Market:

2025-10-08
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More details for 219 Citrus Grove Blvd S, Polk City, FL - Specialty for Sale

219 Citrus Grove Blvd S

Polk City, FL 33868

  • Airbnb Property
  • Specialty for Sale
  • $746,900 CAD
  • 3,774 SF

Polk City Specialty for Sale - Polk County

Nestled in the heart of Polk City, this versatile income-generating property offers a rare opportunity for investors seeking both short-term and long-term rental revenue. Comprising three distinct yet interconnected dwellings—The Cottage, The Cove, and the Main House—this fully remodeled estate spans over 4,325 square feet under roof on a fenced 0.44-acre lot. With a total of 6 bedrooms, 3.5 bathrooms, 3 living rooms, 2 kitchens, and 3 laundry rooms, the layout is ideal for multi-unit occupancy or extended family living. One unit is currently operating as a licensed Airbnb, while another is leased on a yearly basis, offering immediate cash flow. The third unit is available for additional rental or owner occupancy. The property has been thoughtfully updated, including a new roof and granite countertops, and features ample parking for 9+ vehicles plus a 1-car garage. Interior finishes include window treatments and modernized kitchens, with furniture available upon request. Located minutes from I-4 and the Polk Parkway (SR-570), the property enjoys excellent connectivity to Lakeland, Orlando, and Tampa. With no HOA restrictions and a monthly income potential of approximately $4,500 when fully rented, this asset is ideal for investors seeking a turnkey opportunity in a growing Central Florida market.

Contact:

Sand Dollar Realty Group, Team Excellence

Date on Market:

2025-09-16
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