
Vacation rentals near Whispering Forest Trailhead
We found 1,104 vacation rentals — enter your dates for availability
Select the perfect vacation home that's close to Whispering Forest Trailhead. Vacation rentals offer the best amenities for you and your friends, family, or even pets, like air conditioning and WiFi. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Whispering Forest Trailhead
Showing deals for:Nov 7 - Nov 14
Image gallery for Cozy 4/2, on ⭐ Beautiful Lake, 🧡 Hot Tub, 😎 Chill Patio & 🎮 Game/Bunk Room!

1010 out of 10 rating
Exceptional
(8 reviews)
Cozy 4/2, on ⭐ Beautiful Lake, 🧡 Hot Tub, 😎 Chill Patio & 🎮 Game/Bunk Room!
Oviedo, FL
10% off
Price is CA $694
CA $694
CA $6,150 total
CA $6,150 total
includes taxes & fees
Image gallery for Large Luxury Home - Heated Pool - Hot Tub - Close to Beach -Disney

9.09.0 out of 10 rating
Wonderful
(131 reviews)
Large Luxury Home - Heated Pool - Hot Tub - Close to Beach -Disney
Titusville, FL
17% off
Price is CA $401
CA $401
CA $3,577 total
CA $3,577 total
includes taxes & fees
Image gallery for Downtown Floating Bungalow Historic Sanford Lake Monroe Marina

1010 out of 10 rating
Exceptional
(57 reviews)
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Sanford, FL
10% off
Price is CA $208
CA $208
CA $1,874 total
CA $1,874 total
includes taxes & fees
Image gallery for Florida Vacation with pool fun for families

9.69.6 out of 10 rating
Exceptional
(29 reviews)
Florida Vacation with pool fun for families
Casselberry, FL
10% off
Price is CA $173
CA $173
CA $1,727 total
CA $1,727 total
includes taxes & fees
Image gallery for Spacious and relaxing Home - North Of Orlando In Longwood, Florida

9.49.4 out of 10 rating
Exceptional
(32 reviews)
Spacious and relaxing Home - North Of Orlando In Longwood, Florida
Longwood, FL
10% off
Price is CA $380
CA $380
CA $3,566 total
CA $3,566 total
includes taxes & fees
Image gallery for Beautiful 4/2 in Sanford: King Bed, Golf, Pool, Ping Pong, & Bunk Room!

8.88.8 out of 10 rating
Excellent
(11 reviews)
Beautiful 4/2 in Sanford: King Bed, Golf, Pool, Ping Pong, & Bunk Room!
Sanford, FL
10% off
Price is CA $434
CA $434
CA $3,940 total
CA $3,940 total
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly

9.29.2 out of 10 rating
Wonderful
(20 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
10% off
Price is CA $557
CA $557
CA $5,060 total
CA $5,060 total
includes taxes & fees
Image gallery for Relaxing Tropical Pool Home Close to Beach and Disney

9.09.0 out of 10 rating
Wonderful
(68 reviews)
Relaxing Tropical Pool Home Close to Beach and Disney
Titusville, FL
14% off
Price is CA $324
CA $324
CA $2,914 total
CA $2,914 total
includes taxes & fees
Image gallery for Lakeside and Beautiful

1010 out of 10 rating
Exceptional
(29 reviews)
Lakeside and Beautiful
Sanford, FL
10% off
Price is CA $210
CA $210
CA $2,124 total
CA $2,124 total
includes taxes & fees
Image gallery for The Bedford House Countryside

9.89.8 out of 10 rating
Exceptional
(21 reviews)
The Bedford House Countryside
Sanford, FL
10% off
Price is CA $370
CA $370
CA $3,645 total
CA $3,645 total
includes taxes & fees
Image gallery for The Suite at Enchanted Acres Ranch

1010 out of 10 rating
Exceptional
(45 reviews)
The Suite at Enchanted Acres Ranch
Cocoa, FL
10% off
Price is CA $154
CA $154
CA $1,367 total
CA $1,367 total
includes taxes & fees
Image gallery for Fully renovated home in Lake Mary

1010 out of 10 rating
Exceptional
(5 reviews)
Fully renovated home in Lake Mary
Lake Mary, FL
15% off
Price is CA $381
CA $381
CA $3,536 total
CA $3,536 total
includes taxes & fees
Image gallery for Edgewater lake house Sanford/Orlando near SFB

1010 out of 10 rating
Exceptional
(58 reviews)
Edgewater lake house Sanford/Orlando near SFB
Sanford, FL
5% off
Price is CA $241
CA $241
CA $2,268 total
CA $2,268 total
includes taxes & fees
Image gallery for NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!

9.89.8 out of 10 rating
Exceptional
(96 reviews)
NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!
Sanford, FL
10% off
Price is CA $241
CA $241
CA $2,218 total
CA $2,218 total
includes taxes & fees
Image gallery for Charming 1920's House - pet friendly, 45 minutes from beach & attractions!

1010 out of 10 rating
Exceptional
(13 reviews)
Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
Sanford, FL
20% off
Price is CA $272
CA $272
CA $2,493 total
CA $2,493 total
includes taxes & fees
Image gallery for At the Center of it All!

9.89.8 out of 10 rating
Exceptional
(140 reviews)
At the Center of it All!
Titusville, FL
15% off
Price is CA $174
CA $174
CA $1,573 total
CA $1,573 total
includes taxes & fees
Image gallery for Modern, Charming Home in the heart of Winter Park- Perfect for a couples retreat or small group!

9.69.6 out of 10 rating
Exceptional
(11 reviews)
Modern, Charming Home in the heart of Winter Park- Perfect for a couples retreat or small group!
Winter Park, FL
5% off
Price is CA $455
CA $455
CA $3,717 total
CA $3,717 total
includes taxes & fees
Image gallery for *NewRenovatedAPT*KINGbed*PetsOk+Priv Entry

8.08.0 out of 10 rating
Very good
(5 reviews)
*NewRenovatedAPT*KINGbed*PetsOk+Priv Entry
Orlando, FL
5% off
Price is CA $229
CA $229
CA $2,052 total
CA $2,052 total
includes taxes & fees
Image gallery for Cozy Quiet Home in Orlando FL

1010 out of 10 rating
Exceptional
(12 reviews)
Cozy Quiet Home in Orlando FL
Orlando, FL
7% off
Price is CA $424
CA $424
CA $3,846 total
CA $3,846 total
includes taxes & fees
Image gallery for Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.

1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.
Oviedo, FL
18% off
Price is CA $225
CA $225
CA $2,540 total
CA $2,540 total
includes taxes & fees
Image gallery for Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches

9.69.6 out of 10 rating
Exceptional
(28 reviews)
Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches
Sanford, FL
10% off
Price is CA $157
CA $157
CA $1,504 total
CA $1,504 total
includes taxes & fees
Image gallery for Weekday Special Florida Cozy Cottage with queen bed & nearby pickleball courts

1010 out of 10 rating
Exceptional
(15 reviews)
Weekday Special Florida Cozy Cottage with queen bed & nearby pickleball courts
Lake Mary, FL
10% off
Price is CA $130
CA $130
CA $1,273 total
CA $1,273 total
includes taxes & fees
Image gallery for Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park

1010 out of 10 rating
Exceptional
(43 reviews)
Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
Orlando, FL
10% off
Price is CA $391
CA $391
CA $3,495 total
CA $3,495 total
includes taxes & fees
Image gallery for Modern Townhome w/Pool & Private Gym / Boombah Sports / SFB Airport / DT Sanford

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern Townhome w/Pool & Private Gym / Boombah Sports / SFB Airport / DT Sanford
Sanford, FL
10% off
Price is CA $217
CA $217
CA $2,095 total
CA $2,095 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Whispering Forest Trailhead
3 bedroom Modern pool home, Oviedo FL, close to UCF
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Alderwood lake house Sanford/Orlando near SFB
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
109 reviews(109 reviews)
Clear Lake Front home near Orlando / Sanford SFB Boombah
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Mayfair Forrest Retreat ! Come and Enjoy our Clean and Spacious home sleeps 18!
Sleeps 18 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Sleeps 20 · 6 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House
Sleeps 4 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
Top rated rentals - Whispering Forest Trailhead
Home away from home
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Liz was an amazing host and very easy to communicate with. Quiet and safe neighborhood. Felt like being home while on vacation! Definitely our new go to place while in Florida!
Taylor N.
Stayed Jun 2025
Great property in Historic District of Sanford
1010 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
A great mix of historic charm with modern conveniences. Very clean and comfortable. Close to restaurants and shops and Lake Munroe.Would definitely recommend and stay here again if possible.
Garry G.
Stayed May 2025
Wow, what a gem
1010 out of 10
Exceptionalexceptional
251 reviews(251 reviews)
Are you considering a VRBO in Orlando ?
Let me tell you about our experiences.
We have stayed in t VENTURA Country Club three times. It is a 10 minute drive north of the international airport, and only about a 30 minute drive to the major Orlando attractions
It is a gated, moated very quiet complex of condos and private houses. We loved the security and the quiet, zen like atmosphere. There are lots of units, but it is divided into several neighbourhoods, each with its own pool and character. There is a quality, updated golf course, and a great clubhouse with its own massive pool as well as a restaurant, bar , gym and library. Happy hour in the clubhouse is fun, welcoming and inexpensive.
Many of the units available for rent are older, and ok, we have stayed in two of them. This third year we found a fantastic unit. It is on the ground floor, in the quiet Southpointe neighbourhood, and is beautifully renovated. It features granite counters, tile floors, leather furniture, a genuine KING bed in the master bedroom, a second bedroom, three TV’s; as well as air conditioning , a nice ‘Florida’ room and a fully and completely equipped kitchen. It is VRBO # 504312, owned by Jan Dorwath; who is a thoughtful and considerate host. The place is spotless everywhere.
Even though it is only ten minutes from the airport, in our three weeks we only heard an airplane once or twice.; and that was when we were outside. We did hear the neighbour upstairs a couple times, likely when they
George J.
Stayed Nov 2024
Mas de una casa regular- un lugar muy especial y muy maravilloso!
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Heartfelt thanks Jose and Nuria for a beautiful stay in your magnificent and homey Casa Ordoñez. It was lovely to say the least and we had everything we could possibly need for a relaxed and comfortable stay. We appreciate how responsive you were to our questions about the property. It was an added advantage that your location is superb in its proximity to Winter Park Historical Downtown District.
We had a very enjoyable stay and would highly recommend your property to others.
Muchas gracias,
Denise and Jim, Canada
Denise D.
Stayed Aug 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value