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Search results; Over 1,000 homes in Middleburg

Top guest favourite
Guest suite in Middleburg
Secluded, Cozy Guest Suite on Black Creek
1 bedroom, 1 bed, 1 private bathroom
12–17 Oct
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4.99 out of 5 average rating, 122 reviews
Guest favourite
Flat in Middleburg
Florida Postcard Getaway
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 20 reviews
Farm stay in Middleburg
A Private Loft at Grand Landings Equestrian Center
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.87 out of 5 average rating, 276 reviews
Guest favourite
Home in Orange Park
Dogwood Stay: Near the Lake
3 bedrooms, 3 king beds, 2 bathrooms
16–21 Sept
4.9 out of 5 average rating, 71 reviews
Guest favourite
Home in Orange Park
Spacious family hangout spot
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Yurt in Middleburg
Pasture Bedtime Yurt
1 bedroom, 5 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Orange Park
Game Room + Fenced Backyard | Rococo Retreat | 3BR
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Flat in Green Cove Springs
Waterfront Retreat-Dock, Fishing & More!
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Middleburg
Picturesque Middleburg Creek-View Vacation Home!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 68 reviews
Guest favourite
Home in Middleburg
Creek House hideaway NEW HOT TUB !
3 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
4.9 out of 5 average rating, 59 reviews
Superhost
Home in Orange Park
Modern Open Concept 3/2 Retreat
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
New place to stay
Superhost
Townhouse in Orange Park
3BR Townhome, King Suite + Small Dogs
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Place to stay in Orange Park
Beautiful 3 bedroom 2 bathroom waterfront home
3 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.94 out of 5 average rating, 138 reviews
Guest favourite
Home in Orange Park
Gorgeous circa 1875 Plantation House (in city)
6 bedrooms, 8 beds, 3.5 bathrooms
19–24 Sept
4.9 out of 5 average rating, 219 reviews
Superhost
Home in Middleburg
Sunset Pond Views| Perfect For Families
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Jacksonville
4bd 2 bth Home in Oakleaf area! W/Tesla Charger
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Guest house in Orange Park
Graceful Southern Guesthouse + Outdoor Living Area
2 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.91 out of 5 average rating, 191 reviews
Guest favourite
Home in Orange Park
Renovated Modern Retreat • Near Shopping & Dining
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.83 out of 5 average rating, 6 reviews
Guest favourite
Home in Orange Park
Jacuzzi +Gameroom | Rococo Retreat | 4BR Sleeps 10
4 bedrooms, 4 beds, 3 bathrooms
16–21 Sept
4.88 out of 5 average rating, 26 reviews