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Search results; Over 1,000 homes in Middleburg

Guest favourite
Farm stay in Middleburg
Haystays Farm-Cozy, Charming, Country, Modern Home
3 bedrooms, 3 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.97 out of 5 average rating, 240 reviews
Farm stay in Middleburg
A Private Loft at Grand Landings Equestrian Center
1 bedroom, 3 beds
10–15 Sept
4.87 out of 5 average rating, 275 reviews
Guest favourite
Flat in Middleburg
Florida Postcard Getaway
1 bedroom, 1 bed
14–19 Sept
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Middleburg
Sunset Pond Views| Perfect For Families
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Orange Park
Spacious family hangout spot
3 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Jacksonville
4bd 2 bth Home in Oakleaf area! W/Tesla Charger
4 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Clay County
The Cheswick Escape - Team Joseph Ellen
3 bedrooms, 3 beds
20–25 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Fleming Island
The Flemingo- Game Room 3 Kings
3 bedrooms, 4 beds
8–13 Sept
4.96 out of 5 average rating, 206 reviews
Superhost
Home in Fleming Island
Doctor's Lake 5th Wheel Shaded Stay
1 bedroom, 1 bed
9–14 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Fleming Island
Rustic Owl in Fleming Island with 2 Kings
3 bedrooms, 6 beds
7–12 Sept
4.99 out of 5 average rating, 173 reviews
Superhost
Home in Jacksonville
Luxury Pool - 5 bed House.
3 bedrooms, 5 beds
7–12 Sept
4.64 out of 5 average rating, 14 reviews
Guest favourite
Home in Orange Park
Game Room + Fenced Backyard | Rococo Retreat | 3BR
3 bedrooms, 3 beds
14–19 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Orange Park
Dogwood Stay: Near the Lake
3 bedrooms, 3 king beds
13–18 Sept
4.9 out of 5 average rating, 71 reviews
Guest favourite
Home in Middleburg
Modern E. Orange Park Home 6 bed Fence Beach 45 Mn
3 bedrooms, 6 beds
7–12 Sept
4.94 out of 5 average rating, 127 reviews
Guest favourite
Townhouse in Orange Park
New 3BR Townhome, King Suite + Small Dogs
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Orange Park
SKY Vacation Home, Private resort for your family
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guest house in Orange Park
Graceful Southern Guesthouse + Outdoor Living Area
2 bedrooms, 5 beds
7–12 Sept
4.91 out of 5 average rating, 190 reviews
Top guest favourite
Guest suite in Middleburg
Secluded, Cozy Guest Suite on Black Creek
1 bedroom, 1 queen bed
15–20 Sept
4.99 out of 5 average rating, 122 reviews
Top guest favourite
Place to stay in Orange Park
Beautiful 3 bedroom 2 bathroom waterfront home
3 bedrooms, 6 beds
7–12 Sept
4.94 out of 5 average rating, 136 reviews