Holiday rentals near Bear Pond Trailhead
We found 1,273 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 AU$2,901
AU$2,901
AU$414 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 AU$2,880
AU$2,880
AU$411 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 AU$2,371
AU$2,371
AU$339 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 AU$2,762
AU$2,762
AU$395 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 AU$1,575
AU$1,575
AU$225 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 AU$2,884
AU$2,884
AU$412 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 AU$1,961
AU$1,961
AU$280 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 AU$3,859
AU$3,859
AU$551 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$3,731
AU$3,731
AU$533 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 AU$3,131
AU$3,131
AU$447 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 AU$3,282
AU$3,282
AU$469 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 AU$2,100
AU$2,100
AU$300 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 AU$1,693
AU$1,693
AU$242 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
22% off
Price is AU$1,748
AU$1,748
AU$250 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 AU$4,659
AU$4,659
AU$666 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 AU$2,396
AU$2,396
AU$342 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 AU$5,213
AU$5,213
AU$745 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 AU$3,370
AU$3,370
AU$481 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$2,540
AU$2,540
AU$363 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$1,937
AU$1,937
AU$277 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 AU$3,900
AU$3,900
AU$557 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 AU$2,867
AU$2,867
AU$410 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$2,626
AU$2,626
AU$375 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 AU$2,465
AU$2,465
AU$352 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