Holiday rentals near Bear Pond Trailhead
We found 1,213 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:14 Nov - 21 Nov
Image gallery for Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
1010 out of 10 rating
Exceptional
(13 reviews)
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
Mount Dora, FL
5% off
Price is S$2,598
S$2,598
S$371 nightly
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 S$1,974
S$1,974
S$282 nightly
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 S$5,042
S$5,042
S$720 nightly
Includes taxes & fees
Image gallery for Charming 1925 House in the Heart of DeLand.
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Charming 1925 House in the Heart of DeLand.
DeLand, FL
8% off
Price is S$1,396
S$1,396
S$199 nightly
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 S$5,996
S$5,996
S$857 nightly
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 S$1,756
S$1,756
S$251 nightly
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 S$1,973
S$1,973
S$282 nightly
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
8% off
Price is S$3,337
S$3,337
S$477 nightly
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 S$3,386
S$3,386
S$484 nightly
Includes taxes & fees
Image gallery for Lake view Chalet
9.29.2 out of 10 rating
Wonderful
(31 reviews)
Lake view Chalet
Mount Dora, FL
24% off
Price is S$3,284
S$3,284
S$469 nightly
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 S$2,106
S$2,106
S$301 nightly
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 S$1,988
S$1,988
S$284 nightly
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
(21 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is S$4,469
S$4,469
S$638 nightly
Includes taxes & fees
Image gallery for A Delightful Retreat 3/2 1/2 bath Countryside
9.89.8 out of 10 rating
Exceptional
(21 reviews)
A Delightful Retreat 3/2 1/2 bath Countryside
Sanford, FL
7% off
Price is S$3,398
S$3,398
S$485 nightly
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 S$2,551
S$2,551
S$364 nightly
Includes taxes & fees
Image gallery for Historic 1920 Farmhouse on 6 acres,Huge Pool, Chef’s Kitchen,minutes to Mt Dora!
1010 out of 10 rating
Exceptional
(28 reviews)
Historic 1920 Farmhouse on 6 acres,Huge Pool, Chef’s Kitchen,minutes to Mt Dora!
Sorrento, FL
7% off
Price is S$4,080
S$4,080
S$583 nightly
Includes taxes & fees
Image gallery for The Marigold ★ 1 Gig Wi-Fi ★ Minutes to Everything
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Marigold ★ 1 Gig Wi-Fi ★ Minutes to Everything
Mount Dora, FL
8% off
Price is S$1,650
S$1,650
S$236 nightly
Includes taxes & fees
Image gallery for The Carlton* 3 min walk to Downtown Mt. Dora!!
1010 out of 10 rating
Exceptional
(68 reviews)
The Carlton* 3 min walk to Downtown Mt. Dora!!
Mount Dora, FL
12% off
Price is S$2,620
S$2,620
S$374 nightly
Includes taxes & fees
Image gallery for “1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
9.69.6 out of 10 rating
Exceptional
(10 reviews)
“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
Mount Dora, FL
8% off
Price is S$2,698
S$2,698
S$385 nightly
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 S$2,469
S$2,469
S$353 nightly
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
12% off
Price is S$3,296
S$3,296
S$471 nightly
Includes taxes & fees
Image gallery for Walk into Tropical Paradise - POOL - GYM - HOT TUB
1010 out of 10 rating
Exceptional
(5 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Altamonte Springs, FL
8% off
Price is S$5,663
S$5,663
S$809 nightly
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 S$2,329
S$2,329
S$333 nightly
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 S$1,409
S$1,409
S$201 nightly
Includes taxes & fees
Find spaces that suit your style
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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
59 reviews(59 reviews)
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
65 reviews(65 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)
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)
1887 Royellou House 3BR 2BA
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
155 reviews(155 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