Oakland Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Oakland, Kentucky, USA

The Maple Retreat - Supreme Cabin
10.0 (7 Reviews)
2 Bedrooms 4 Guests
Charming Smiths Grove Home Near Cave Tours!
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10.0 (7 Reviews)
2 Bedrooms 5 Guests
Updated Apt: 1 Mi to Western Kentucky University!
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10.0 (1 Review)
1 Bedroom 2 Guests
The Maple Retreat - Junior Cabin
10.0 (3 Reviews)
2 Bedrooms 4 Guests
Inviting Bowling Green Escape w/Smart TVs!
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
The Maple Retreat at Park Mammoth
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8.8 (16 Reviews)
1 Bedroom 2 Guests
4 Mi to Mammoth Cave: Hand-Built Cabin on 70 Acres
10.0 (1 Review)
1 Bedroom 4 Guests
4 Mi to Mammoth Cave: Hand-Built Cabin on 70 Acres
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10.0 (1 Review)
1 Bedroom 4 Guests
Brownsville Vacation Rental Near National Park!
9.8 (19 Reviews)
2 Bedrooms 6 Guests
Glasgow Getaway w/Patio, Fireplace & Grill!
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9.7 (3 Reviews)
2 Bedrooms 8 Guests
Pet-Friendly Brownsville Retreat w/Porch!
9.4 (43 Reviews)
2 Bedrooms 6 Guests
Bowling Green Townhome: 4 Mi to Lost River Cave!
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9.6 (6 Reviews)
2 Bedrooms 4 Guests
Brownsville Studio Cottage - Walk to Mammoth Cave!
9.4 (39 Reviews)
1 Bedroom 4 Guests
Rocky Hill Inn
From£131 per night
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9.3 (4 Reviews)
3 Bedrooms 6 Guests
The Maple Retreat-Log Cabin
9.0 (2 Reviews)
1 Bedroom 4 Guests
Brownsville Studio Cottage - Walk to Mammoth Cave!
9.0 (11 Reviews)
1 Bedroom 4 Guests
SUADA-Superior ADA Cabin
New
1 Bedroom 4 Guests
Updated Apt: 1 Mi to Western Kentucky University!
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9.0 (8 Reviews)
3 Bedrooms 6 Guests
Vintage BG Home — Historic Charm, Prime Location
10.0 (1 Review)
3 Bedrooms 6 Guests
Lakeside cottage w/3 bed, 2 bath & spectacular view!
9.0 (2 Reviews)
3 Bedrooms 6 Guests
log home Only 10 min from Mammoth Cave Nat Park
10.0 (47 Reviews)
3 Bedrooms 8 Guests
Brownsville Vacation Rental Near National Park!
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9.0 (1 Review)
2 Bedrooms 6 Guests
Pet-Friendly Brownsville Retreat w/Porch!
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8.8 (5 Reviews)
2 Bedrooms 6 Guests
Bowling Green Farmhouse 10 Mi to Mammoth Cave
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8.0 (5 Reviews)
2 Bedrooms 4 Guests
Beautiful cottage with AMAZING view of Barren River Lake!
10.0 (171 Reviews)
3 Bedrooms 9 Guests
Kentucky Vacation Rental: Half-Mi to Mammoth Cave!
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7.9 (10 Reviews)
3 Bedrooms 6 Guests
Sleepover 1BD 1BA Downtown Bowling Green Apartments
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7.4 (90 Reviews)
28 Bedrooms 75 Guests
Lake front, Romantic Honeymoon Getaway.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Bowling Green Vacation Rental Near WKU and Downtown!
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1.0 (1 Review)
2 Bedrooms 5 Guests
Simply Sailing - A Cottage In The Trees
10.0 (77 Reviews)
2 Bedrooms 4 Guests
Bowling Green House w/Shared Pool!
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New
5 Bedrooms 10 Guests
Firestone's @ BRL 14mi-Mammoth Cave. Fire pit!
10.0 (76 Reviews)
3 Bedrooms 6 Guests
5 Mi to Cave Tour! Couples Adventure Hub
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New
2 Bedrooms 4 Guests
Nonna’s Place - Pole Barn Dwelling Near Mammoth Cave
10.0 (71 Reviews)
3 Bedrooms 6 Guests
Creekside Cabin ~ 10 Mi. from Bowling Green!
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New
2 Bedrooms 6 Guests
the Red Door Lakeside
10.0 (64 Reviews)
3 Bedrooms 8 Guests
Relax in the Country and Bring Your Show Car
10.0 (50 Reviews)
1 Bedroom 3 Guests
Tranquil Cabin on Barren River Lake
10.0 (45 Reviews)
3 Bedrooms 8 Guests
Sweet Home 2
From£168 per night
10.0 (3 Reviews)
4 Bedrooms 11 Guests
Embassy Suites by Hilton Bowling Green
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9.6 (837 Reviews)
1 Bedroom 2 Guests
Drury Inn & Suites Bowling Green
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9.4 (1121 Reviews)
1 Bedroom 2 Guests
Creekview at Bays Fork Creekn
10.0 (2 Reviews)
3 Bedrooms 8 Guests
Embassy Suites By Hilton Bowling Green
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9.5 (372 Reviews)
195 Bedrooms 36 Guests
The Hotel Sync
From£108 per night
9.4 (823 Reviews)
1 Bedroom 2 Guests
Holiday Inn Express - Bowling Green by IHG
9.2 (201 Reviews)
175 Bedrooms 30 Guests
Staybridge Suites Bowling Green by IHG
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9.0 (551 Reviews)
87 Bedrooms 46 Guests
Cottage at Sunnyside/Private/5 Wooded Acres/Garage
10.0 (2 Reviews)
1 Bedroom 6 Guests
Drury Inn & Suites Bowling Green
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8.9 (840 Reviews)
134 Bedrooms 26 Guests
Candlewood Suites Bowling Green by IHG
8.9 (145 Reviews)
128 Bedrooms 24 Guests
Sweet Home C
From£295 per night
10.0 (1 Review)
4 Bedrooms 11 Guests
Fairfield Inn & Suites by Marriott Bowling Green
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8.9 (103 Reviews)
106 Bedrooms 56 Guests
Lil' Rock - close to Beech Bend
10.0 (1 Review)
3 Bedrooms 6 Guests
TownePlace Suites by Marriott Bowling Green
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8.9 (47 Reviews)
101 Bedrooms 18 Guests
Woodside Retreat-B: Modern Home
10.0 (1 Review)
2 Bedrooms 5 Guests
Tru By Hilton Bowling Green
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8.7 (357 Reviews)
87 Bedrooms 18 Guests
Sweet home B
From£125 per night
10.0 (1 Review)
3 Bedrooms 8 Guests
Home2 Suites By Hilton Bowling Green
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8.7 (80 Reviews)
81 Bedrooms 26 Guests
SpringHill Suites by Marriott Bowling Green
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8.7 (66 Reviews)
128 Bedrooms 20 Guests

About Oakland Vacation Rentals

With more than 334 Oakland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Oakland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Oakland, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Oakland. Places to stay near Oakland are 648.08 ft² on average, with prices averaging £152 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Oakland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Oakland, KY


Frequently Asked Questions About Oakland?

What are the top vacation rentals in Oakland?

How many Rentbyowner vacation rentals are available in Oakland?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 334 in the Oakland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oakland.