Holiday rentals near Bear Pond Trailhead
We found 1,222 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:21 Nov - 28 Nov
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 AU$3,422
AU$3,422
AU$489 per night
includes taxes & fees
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 AU$3,363
AU$3,363
AU$480 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 AU$6,204
AU$6,204
AU$886 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
(14 reviews)
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Mount Dora, FL
7% off
Price is AU$2,421
AU$2,421
AU$346 per night
includes taxes & fees
Image gallery for Lake Cottage Minutes from Downtown Mount Dora!
1010 out of 10 rating
Exceptional
(75 reviews)
Lake Cottage Minutes from Downtown Mount Dora!
Mount Dora, FL
8% off
Price is AU$2,419
AU$2,419
AU$346 per night
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
8% off
Price is AU$2,142
AU$2,142
AU$306 per night
includes taxes & fees
Image gallery for Lake Lucy Waterfront Home with BBQ & Jon Boat
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Lake Lucy Waterfront Home with BBQ & Jon Boat
Orlando, FL
12% off
Price is AU$2,833
AU$2,833
AU$405 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
(49 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is AU$6,182
AU$6,182
AU$883 per night
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
8% off
Price is AU$5,223
AU$5,223
AU$746 per night
includes taxes & fees
Image gallery for Charming 1925 House in the Heart of DeLand.
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Charming 1925 House in the Heart of DeLand.
DeLand, FL
8% off
Price is AU$1,691
AU$1,691
AU$242 per night
includes taxes & fees
Image gallery for The Retreat - Fast Wi-Fi - Heart of Mount Dora
9.69.6 out of 10 rating
Exceptional
(7 reviews)
The Retreat - Fast Wi-Fi - Heart of Mount Dora
Mount Dora, FL
8% off
Price is AU$2,656
AU$2,656
AU$379 per night
includes taxes & fees
Image gallery for Lakeside and Beautiful
1010 out of 10 rating
Exceptional
(29 reviews)
Lakeside and Beautiful
Sanford, FL
7% off
Price is AU$2,424
AU$2,424
AU$346 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 AU$2,525
AU$2,525
AU$361 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is AU$4,703
AU$4,703
AU$672 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
13% off
Price is AU$3,647
AU$3,647
AU$521 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 AU$3,059
AU$3,059
AU$437 per night
includes taxes & fees
Image gallery for Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Mount Dora, FL
15% off
Price is AU$2,608
AU$2,608
AU$373 per night
includes taxes & fees
Image gallery for Mount Dora Historic District - 1 Bedroom 1 Bathroom Cottage Walk To Town!
1010 out of 10 rating
Exceptional
(5 reviews)
Mount Dora Historic District - 1 Bedroom 1 Bathroom Cottage Walk To Town!
Mount Dora, FL
8% off
Price is AU$1,713
AU$1,713
AU$245 per night
includes taxes & fees
Image gallery for Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora
1010 out of 10 rating
Exceptional
(67 reviews)
Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora
Mount Dora, FL
8% off
Price is AU$2,518
AU$2,518
AU$360 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 AU$1,931
AU$1,931
AU$276 per night
includes taxes & fees
Image gallery for Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Sanford, FL
8% off
Price is AU$1,808
AU$1,808
AU$258 per night
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
16% off
Price is AU$2,794
AU$2,794
AU$399 per night
includes taxes & fees
Image gallery for Cozy Cottage 3 blocks from town
1010 out of 10 rating
Exceptional
(34 reviews)
Cozy Cottage 3 blocks from town
Mount Dora, FL
8% off
Price is AU$1,576
AU$1,576
AU$225 per night
includes taxes & fees
Image gallery for Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
1010 out of 10 rating
Exceptional
(15 reviews)
Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
Lake Mary, FL
7% off
Price is AU$1,442
AU$1,442
AU$206 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Bear Pond Trailhead
Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
385 reviews(385 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
60 reviews(60 reviews)
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
Relax by the pool at this retreat near parks, kayaking, and downtown.
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
168 reviews(168 reviews)
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Serene Lakefront Retreat - Spacious and Cozy Chateau with Country Flair!
Sleeps 11 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 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