185 Windwood Bay

5 BR
4 Baths
Sleeps 10

Promotional Discounts Available! Looking for a deal? We’ve got you covered! Discounts kick in automatically based on how long you stay—no promo codes or special requests needed. Special rates automatically apply for stays of 5 nights, 7 nights, and 28+ nights! The price you see already includes your savings, so you can book worry-free! (Heads up: discounts might show up a little differently depending on the booking site, but they’re always built into your total.)

Nice well maintained community

Enjoy a relaxing getaway in this beautifully updated 5-bedroom, 3.5+ bathroom private pool home in the sought-after Windwood Bay community! Conveniently located near major highways, this home offers easy access to Central Florida’s top attractions.

Inside, you’ll find plenty of space to spread out and unwind with stylish upgraded furniture, modern décor, and deluxe sleeping accommodations. The living area features plush seating, two recliners, and a large wall-mounted flat-screen TV for cozy movie nights. The dining area seats six, with additional breakfast bar seating for two.

The fully equipped kitchen boasts granite countertops, upgraded black appliances, and all the essentials to whip up full meals or quick snacks.

Step outside to your oversized lanai and private splash pool, complete with lounge seating, a pool safety fence, and no rear neighbors—perfect for relaxing days and fun-filled evenings!

NEWLY ADDED: A garage game room for even more entertainment! Ready to make unforgettable memories? Book your stay today!

GROUND FLOOR: (1.5 bathrooms)

• Shared Hall Half Bathroom w/Pedestal Sink

• Shared Half Bathroom Located in Laundry Area

• Full-sized washer and dryer

SECOND FLOOR: (5 Bedrooms | 7 beds | 3 bathrooms)

• King Master Bedroom w/En-Suite Bathroom, Walk In Closet and Flat Screen TV and private bathroom

• 2 Queen Bedrooms w/Flat Screen TV and Spacious Closets

• Two Shared Hall Bathrooms w/Shower & Tub Combinations

• Two Twin Bedrooms w/Two Twin Beds each

ADDITIONAL FEATURES:

• Contact Free Check In and Check Out

• Free Wi-Fi

• Cable and Streaming Television

• Newly Installed Laminate Flooring In Most Rooms

• Main Living Area w/ Flat Screen TV

• Upgraded Living Room Furniture

• Granite Countertops in the Kitchen

• Newly Remodeled En-Suite Bathroom To King Bedroom

• Ceiling Fans Throughout

• Brand New Garage Game Room!

• Large Laundry Room w/Upgraded Washing Machine & Dryer

• Iron & Ironing Board

• Hair Dryers

• Linens & Towels

And Much More!

MANAGER'S NOTES:

**While this is a pet-friendly home, not all pets are accepted. If a pet is traveling with you, please contact our reservations team and let us know!

ALL pets require:

• $150 non-refundable fee (per pet)

• $500 refundable damage deposit (per pet)

• Completed and approved pet profile (our reservations team will provide more details)

Unapproved pets, even in pet-friendly homes, are subject to fines and fees. Please help keep our units pet-friendly and let us know your furbabies are coming!

Sleeping Arrangements

Second Floor King Master King
Second Floor Queen Bedroom Queen
Second Floor Queen Bedroom Queen
Second Floor Twin Bed Room Twin (2)
Second Floor Twin Bed Room Twin (2)

Bathroom Configuration

Ground Floor Shared: Toilet
Second Floor Shared Bathroom: Toilet, Combo Tub Shower
Second Floor Shared: Toilet, Combo Tub Shower
Second Floor Master Bath: Shower, Tub

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed

Amenities

Air Conditioning
Arcade Games
Bathtub
Bed Linens
Big Screen TV
Cable
Car Recommended
Carbon Monoxide Detector
Children Welcome
Cleaning Disinfection
Clothes Dryer
Coffee Maker
Common Surface Disinfectant Cleaned
Cooking Basics
DVD
Deadbolt Lock
Deck Patio Uncovered
Dining Table
Dishes And Silverware
Dishwasher
Disinfected
Downtown
Dryer
Enhanced Cleaning
Essentials
Extra Pillows And Blankets
Family
Fenced Pool
Fire Extinguisher
First Aid Kit
Foosball
Free Wifi
Game Room
Garden Or Backyard
Hair Dryer
Hair-Dryer
Hangers
Heating
Hospital
Hot Water
House Cleaning Included
Ice Maker
Internet
Internet Access
Iron Board
Iron and Board
Kitchen
Laundry
Linens
Living Room
Microwave
Minimum Age Limit
Optional Pool Heat
Outlet Shopping
Oven
Parking
Patio
Pet Friendly
Pets Considered
Pool
Pool Table
Private Pool
Private-Entrance
Private-Living-Room
Refrigerator
Self Check-In
Self Checkin Checkout
Shampoo
Shopping
Smoke Detector
Stove
Swimming
Television
Theme Parks
Toaster
Towels
Tv
WIFI
Washing Machine
Water Parks
Wireless Internet
Bar
Bed Linens Provided
Family Friendly
Food
Gift Shop
Lodging
Lounge
Park
Point Of Interest
Public Transportation
Restaurant
Wifi

Map

Videos

Frequently Asked Questions

If you’d like to request an early check-in, late checkout, or extend your stay, please reach out to our reservations team at least 48 hours in advance. While we can’t guarantee every request, we’ll do our very best to accommodate you! Please note that same-day requests can rarely be honored, and some changes may require additional fees.
 
**While this is a pet-friendly home, not all pets are accepted. If a pet is traveling with you,  please contact our reservations team and let us know! 

ALL pets require: 
• $100 non-refundable fee (per pet)
• $500 refundable damage deposit (per pet)
• Completed and approved pet profile (our reservations team will provide more details)

Unapproved pets, even in pet-friendly homes, are subject to fines and fees. Please help keep our units pet-friendly and let us know your furbabies are coming!
Typically, maid service is only scheduled for after your departure. If you would like to add a cleaning stop during your stay, just reach out and let us know! Prices vary on the size of the home. 

*We do require ONE full cleaning visit for every 30 days stayed with us. Our reservations team will work with you to schedule these additional cleanings.  
REQUIREMENTS
​This is a pet-friendly home, with a max of 2. ALL pets require: 
  • $150 non-refundable fee (per pet)
  • $500 refundable security deposit (per pet)
  • Completed and approved Pet Profile
​RULES
  • Florida Law requires ALL pets to have a current rabies vaccination. 
  • Please do your best to keep pets off of beds and furniture.
  • When outside, pets MUST be on a leash.
  • Tenant is required to bring supplies to pick up after the pet both indoors and outdoors. 
  • No pets are allowed in the pool at any time.
  • It is strongly recommended that pets be crated when left alone in the home. 
  • Money will be held back from the refundable pet deposit if additional cleaning of the home is needed due to remaining pet hair and dander.
  • Any damages to the home or its contents by the pet will be held from the deposit, and additional fines may be assessed if damages total more than the deposit. 
A: YES! If you would like to add pool heat to your reservation, please contact us after confirming your booking!

It is important to keep in mind: 
  • Pool heat is available from varying dates in October through April.
  • Pool heat requires a minimum of 3 nights' purchase 
  • Pool heat is set at a constant 85 Fahrenheit/29.4 Celsius and is NOT ADJUSTABLE
  • The pool heater will heat the water 10-15 degrees above the outside ambient temperature (if the outside temperature is 65F the water can be expected to be 75F)
  • Pool heaters will not work if the ambient outside temperature falls below 55 Fahrenheit/16 Celsius.
  • The pool heater only runs when the pool pumps are circulating the water, which is not 24/7. Most pumps turn off to conserve power after 8p.
  • Please double-check your listing; spas are not hot tubs and spa temperature will be the same temperature as the pool.
  • No refunds will be given if local weather conditions cause the pool water temperature to fall short of expectations.
CHECK-IN 4:00PM EST
CHECKOUT 10:00AM EST
Please be aware that during peak or holiday seasons, 4p check-in may not be guaranteed. Our team will be in touch if your check-in needs to be slightly delayed. Entering the home before the agreed-upon time or not checking out by the agreed-upon time carries fines.

AGE RESTRICTIONS - The primary renter must be 25+ years of age and proof may be required at any time.

PRIMARY RENTER - The primary renter must be staying in the unit for the full duration of the trip. No arbitrage or 3rd party bookings are allowed or will be honored. Please make sure the information we have (phone number, email address) for the primary renter is accurate and up to date at all times.

NO SMOKING OR VAPING - Smoking and/or vaping of any kind is strictly prohibited. Florida law prohibits smoking/vaping on balconies of shared housing (condos/apartments) or shared entryways with other units. Fines starting at $500 will be issued for ANY evidence of smoking or vaping is found in the unit after your departure (including smell).

ENTRY BY OWNER - The owner or owner's agents may enter the premises due to an emergency, necessary/agreed-upon repairs/alterations/improvements/services, or showing to prospective purchasers, renters, or contractors.

FURNISHINGS - Do not move or remove any furnishings from the premises or property. Fines will be incurred for theft or damages.

GARBAGE - The tenant is responsible for the collection and removal of all trash during the stay. Specific trash instructions will be shared in your welcome letter.

HAZARDOUS PRACTICES - No grills of any kind are permitted inside or in any covered areas. Grills may be used only in open-air areas 50+ feet away from the home. No open flames (e.g., candles, turkey fryers, etc) are permitted on the premises. Do not dismantle smoke, carbon monoxide detectors, or pool alarms as they are for your protection.

HOLD HARMLESS - iTrip nor the Owner of the premises assume any liability for (i) loss, damage, illness, or injury to persons or their personal property that occurs during their stay on the premises; (ii) any inconveniences, damage, loss, or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, internet access, electricity or plumbing or (iii) any inconveniences, damage, loss or injury arising from or due to weather conditions, natural disasters, acts of God, or other reasons beyond their control.

PARKING - Parking is limited to the designated area(s) and guests assume all risks. Neither the Owner, Owners Association, nor iTrip is responsible for any vehicle damage/theft. No boats, jet skis, campers, trailers, or RVs, are allowed. Please check your welcome letter for specific HOA rules regarding parking.

UNIT OCCUPANCY/DISTURBANCES - The maximum occupancy is based on the property limitations in the rental reservation. No parties or events are allowed. Tenants will be removed, fined, and will forfeit all monies for: Exceeding maximum occupancy, planning, marketing or hosting a party; or any acts that interfere with neighbors’ right to quiet of their premises. Quiet Time: 10:00PM – 8:00AM

RESPECTFUL BEHAVIOR - Please treat the home, the neighbors, the community, and our team of iTrip Staff and contractors with respect; we will do the same.

CANCELLATION POLICY - CANCEL FOR ANY REASON TRAVEL INSURANCE IS HIGHLY RECOMMENDED. Our cancellation policy is as agreed to at the time of booking. All cancellations and date alterations are subject to our cancellation policy and exemptions will not be made. We will ONLY provide refunds for nights that a local government body has issued a MANDATORY evacuation.

DAMAGES/FINES - Accidents happen, but you are responsible for any damages, additional cleanings, or service provider call-out fees that are required because of your stay. Fines or fees may be assessed for (but are not limited to): unapproved early check-in, unapproved late check-out, unapproved pets, unapproved guests, smoking or vaping of any kind, missing or damaged items, stains, tears, rips, trash left in the home, HOA-issued fines for violations, service provider calls for guest caused issues, service calls for guest reported issues that aren't issues (ex: Pool Heat, HVAC, etc) etc. Please report any damages as soon as possible so we can work to resolve them.

VIOLATION OF THESE RULES - Violation of any part of this agreement may result in fees, fines, and/or the immediate termination of the booking, with forfeiture of all monies paid. iTrip Orlando reserves the right to cancel the Tenant’s stay with no refund if the tenant and/or their guests fail to comply with any of the rules outlined in this agreement. Eviction with no monies due will occur for any of the following:
• Occupancy exceeding the sleeping capacity of the home (10), 24 hours per day, 7 days per week, 365 days per year
• Using the premises for any illegal activity
• Intentionally causing damage to the rented premises or to any of the neighboring properties and any other acts that interfere with neighbors' right to quiet enjoyment of their premises
• Party planning, advertising for a party, or parties in the home or on the property
• Smoking or evidence of smoking in the property
• Unauthorized Pets
• Threats of acts or violence towards any representatives of iTrip Orlando, neighboring occupants, Resort staff, etc
• Violation of any Resort, HOA, Local, State, and/or Federal laws

ISSUE REPORTING, RESOLUTION, & REFUND REQUESTS - Guests must immediately notify iTrip Orlando of any maintenance concerns, cleaning issues, repair requests, or other problems upon discovery. Reports should include relevant supporting evidence, such as photos or videos. Upon notification, guests must allow iTrip Orlando access to the home to investigate and address the issue; in most cases, guests do not need to be present for this access. If the reported issue is resolved, no further remuneration or refund will be provided. If a guest is unresponsive or denies iTrip Orlando access to the home, we will assume the issue has been resolved, and no further action will be taken.

Any issues reported after checkout are not eligible for compensation. No refunds will be given for acts of God or Nature or items out of our control (public utilities such as power, water, internet, natural gas, etc., road closures, resort amenity closures, etc). If a reported issue is determined to be a false report—meaning it cannot be confirmed, replicated, is due to guest misunderstanding—or if the issue is caused by the guest (e.g., clogged drains, misuse of HVAC systems), the guest may be charged a service call out call fee in addition to any repair costs. The guest will be responsible for any expenses related to clearing blockages in drain lines, sewer lines, or garbage disposals caused by their actions. Fines may be assessed for damage resulting from improper use or tampering with property systems, including pool equipment, HVAC units (e.g., causing freeze-ups), or other mechanical components.

EMAIL & TEXT CONSENT - By providing your email address and phone number you are giving iTrip Orlando consent to provide their services and communicate with you via mobile phone, messages, e-mail, and any kind of online communications, provided that these communications comply with privacy regulations.

YOUR INFORMATION - We take the protection of your personal information INCREDIBLY seriously. In some cases, your name, email address, and/or phone number may be shared with vendors so they can properly assist during your stay. Some communities REQUIRE us to provide guest names, stay dates, and/or copies of government-issued identification.

Reviews

Great stay
5/5 stars
Our stay was extremely enjoyable. The house was clean and supplied plenty of linens. We had a small problem with the pool but itrip responded quickly and someone was there immediately to fix the problem. Our dogs loved the fenced in backyard. Great to have the washer and dryer. Very fast dryer, which was a plus too. I would definitely stay at this house again, and would definitely book with itrip again also.
- Steve

Thank you for your review Steve we have shared with our team and look forward to your next stay with us. Thank you.

- Manager Response
Great Vacation
5/5 stars
The home at 185 Winwood Bay was a great choice and Premier Resort Properties was great to work with concerning any questions we had and the minimal response time. I would certainly do business with them again.
- David

Thank you for your review David we have shared with our team and look forward to your next stay with us. Thank you.

- Manager Response
Spacious and Gracious
5/5 stars
This was a great place to stay. 5 bedrooms! So much space and a nice outdoor area with a pool. It also had a backyard for doing some exercise. Super easy to find and near the highway. I felt safe in the neighborhood and was close to a lot of restaurants and amenities (grocery, gas, gym, etc.) The host was super responsive and friendly. Easy 5-star review, and I would come back again.
- Jason

Thank you for your review Jason we have shared with our team and look forward to your next stay with us. Thank you.

- Manager Response

Book Your Stay

SuMoTuWeThFrSa
123456789101112131415161718192021222324252627282930123456789101112
SuMoTuWeThFrSa
123456789101112131415161718192021222324252627282930123456789101112
Select your trip dates.
Contact Manager

Toll Free (888) 847-0086