Holiday rentals near Bear Pond Trailhead
We found 1,270 holiday rentals — enter your dates for availability
If you'd like to stay close to Bear Pond Trailhead, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Bear Pond Trailhead
Showing deals for:3 Oct - 10 Oct
Image gallery for ORL Modern Zen Vibe Brand new 2/2 construction in the Heart of Downtown Orlando
1010 out of 10 rating
Exceptional
(8 reviews)
ORL Modern Zen Vibe Brand new 2/2 construction in the Heart of Downtown Orlando
Orlando, FL
8% off
Price is NZ$3,158
NZ$3,158
NZ$451 per night
includes taxes & fees
Image gallery for Orlando 1 Acre 4 BD Home Central Near Universal
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Orlando 1 Acre 4 BD Home Central Near Universal
Orlando, FL
16% off
Price is NZ$3,120
NZ$3,120
NZ$446 per night
includes taxes & fees
Image gallery for Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
1010 out of 10 rating
Exceptional
(13 reviews)
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Mount Dora, FL
7% off
Price is NZ$2,536
NZ$2,536
NZ$362 per night
includes taxes & fees
Image gallery for The Augustine · Complete Renovation - Steps to Downtown w King Bed
1010 out of 10 rating
Exceptional
(27 reviews)
The Augustine · Complete Renovation - Steps to Downtown w King Bed
Mount Dora, FL
12% off
Price is NZ$2,975
NZ$2,975
NZ$425 per night
includes taxes & fees
Image gallery for Family Time! This Cute Cottage is waiting you for a unique experience!
9.89.8 out of 10 rating
Exceptional
(75 reviews)
Family Time! This Cute Cottage is waiting you for a unique experience!
Umatilla, FL
11% off
Price is NZ$1,674
NZ$1,674
NZ$239 per night
includes taxes & fees
Image gallery for THE CHLOE by EVRH
9.09.0 out of 10 rating
Wonderful
(61 reviews)
THE CHLOE by EVRH
Altamonte Springs, FL
7% off
Price is NZ$3,123
NZ$3,123
NZ$446 per night
includes taxes & fees
Image gallery for Florida Vacation with pool fun for families
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Florida Vacation with pool fun for families
Casselberry, FL
7% off
Price is NZ$2,086
NZ$2,086
NZ$298 per night
includes taxes & fees
Image gallery for Lake Vibes Only ~ Lake House with RV or Boat Parking!
1010 out of 10 rating
Exceptional
(30 reviews)
Lake Vibes Only ~ Lake House with RV or Boat Parking!
Mount Dora, FL
12% off
Price is NZ$4,183
NZ$4,183
NZ$598 per night
includes taxes & fees
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
8% off
Price is NZ$4,044
NZ$4,044
NZ$578 per night
includes taxes & fees
Image gallery for Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Orlando, FL
8% off
Price is NZ$3,388
NZ$3,388
NZ$484 per night
includes taxes & fees
Image gallery for The Beauclair * 3 min walk to Downtown Mt. Dora!!
1010 out of 10 rating
Exceptional
(46 reviews)
The Beauclair * 3 min walk to Downtown Mt. Dora!!
Mount Dora, FL
8% off
Price is NZ$3,559
NZ$3,559
NZ$508 per night
includes taxes & fees
Image gallery for The Retreat - Fast Wi-Fi - Heart of Mount Dora
9.49.4 out of 10 rating
Exceptional
(6 reviews)
The Retreat - Fast Wi-Fi - Heart of Mount Dora
Mount Dora, Florida
7% off
Price is NZ$2,245
NZ$2,245
NZ$321 per night
includes taxes & fees
Image gallery for Charming 1925 House in the Heart of DeLand.
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Charming 1925 House in the Heart of DeLand.
DeLand, FL
8% off
Price is NZ$1,800
NZ$1,800
NZ$257 per night
includes taxes & fees
Image gallery for Lake Lucy Waterfront Home with BBQ & Jon Boat
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Lake Lucy Waterfront Home with BBQ & Jon Boat
Orlando, FL
23% off
Price is NZ$1,860
NZ$1,860
NZ$266 per night
includes taxes & fees
Image gallery for Private Oasis near Springs w/ King Bd + Pool Table
9.09.0 out of 10 rating
Wonderful
(9 reviews)
Private Oasis near Springs w/ King Bd + Pool Table
Apopka, FL
15% off
Price is NZ$5,039
NZ$5,039
NZ$720 per night
includes taxes & fees
Image gallery for Lakeside and Beautiful
1010 out of 10 rating
Exceptional
(27 reviews)
Lakeside and Beautiful
Sanford, FL
7% off
Price is NZ$2,564
NZ$2,564
NZ$366 per night
includes taxes & fees
Image gallery for Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
1010 out of 10 rating
Exceptional
(47 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is NZ$5,636
NZ$5,636
NZ$805 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.49.4 out of 10 rating
Exceptional
(17 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is NZ$3,662
NZ$3,662
NZ$523 per night
includes taxes & fees
Image gallery for Waterfront home .5 miles from downtown Tavares and 10 minutes from Harris Chain.
1010 out of 10 rating
Exceptional
(20 reviews)
Waterfront home .5 miles from downtown Tavares and 10 minutes from Harris Chain.
Tavares, FL
8% off
Price is NZ$2,719
NZ$2,719
NZ$388 per night
includes taxes & fees
Image gallery for Floating Cottage Summer and Fall Rates Reduced
1010 out of 10 rating
Exceptional
(157 reviews)
Floating Cottage Summer and Fall Rates Reduced
Sanford, FL
11% off
Price is NZ$2,061
NZ$2,061
NZ$294 per night
includes taxes & fees
Image gallery for Lake view Chalet
9.29.2 out of 10 rating
Wonderful
(30 reviews)
Lake view Chalet
Mount Dora, FL
24% off
Price is NZ$4,220
NZ$4,220
NZ$603 per night
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
12% off
Price is NZ$3,104
NZ$3,104
NZ$443 per night
includes taxes & fees
Image gallery for All New Deland Den 4BR, pool, blocks fr Stetson & Downtown
9.69.6 out of 10 rating
Exceptional
(11 reviews)
All New Deland Den 4BR, pool, blocks fr Stetson & Downtown
DeLand, FL
8% off
Price is NZ$2,843
NZ$2,843
NZ$406 per night
includes taxes & fees
Image gallery for Lake Cottage with screen patio, fire pit and dock, close to downtown Mt Dora
9.89.8 out of 10 rating
Exceptional
(82 reviews)
Lake Cottage with screen patio, fire pit and dock, close to downtown Mt Dora
Mount Dora, FL
8% off
Price is NZ$2,640
NZ$2,640
NZ$377 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Bear Pond Trailhead
Serene Lakefront Retreat - Spacious and Cozy Chateau with Country Flair!
Sleeps 11 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Adorable Private Tiny Home "The Pink House" in Downtown Mt. Dora!! Pet Friendly
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
379 reviews(379 reviews)
"THE FISHERMAN'S COTTAGE" Historic District-Mount Dora's # 1 DESTINATION Rental!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Historic Tremain Cottages
Sleeps 3 · 1 bedroom
8.48.4 out of 10
Very goodvery good
31 reviews(31 reviews)
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
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, gardens and more
More for lessMore space, more privacy, more amenities — more value