Home Vacation Rentals By Owner In Owensboro, KY

Showing 20 Of 37 Vacation Rentals
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Exceptional(11)

$220.86

/ Nightly
Cabin

Log Cabin Retreat in Kentucky: Fire Pit & Grill!

Owensboro, Kentucky, United States

Surrounded By 10 Wooded Acres | Furnished Lake-View Deck | Dogs Welcome w/ FeebrbrUnplug and unwind at this one-of-a-kind Owensboro vacation rental, where the charm of a log cabin meets the tranquility of a secluded getaway. The 3-bedroom, 1-bath home promises a rejuvenating retreat with loved ones, whether you enjoy warm evenings beside the stone fireplace or lively afternoons lounging on the deck. Book today and get ready to discover the magic of this woodland gem!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 2 queen bedsbr- Bedroom 2: 1 bunk bed (twin/full)br- Bedroom 3 (Loft): 1 full bedbrbrINDOOR LIVINGbr- Fireplace, flat-screen TVbr- Dining tablebr- Work deskbr- Wood-burning stove (decorative only)brbrOUTDOOR LIVINGbr- 2 decks, outdoor seatingbr- Patio, fire pit, charcoal grillbr- Lake views (no lake access)br- 10-acre propertybrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Drip coffee maker, cooking basics, dishware & flatwarebr- Trash bags & paper towelsbrbrGENERALbr- Central heating & A/Cbr- Towels & linens, complimentary toiletries, hair dryerbr- Washer & dryerbr- Free WiFi, keyless entrybrbrFAQbr- 1 exterior security camera (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-story home, 3 steps to enterbrbrPARKINGbr- Driveway (5 vehicles)brbr-- THE LOCATION --brbr- 0.6 miles to Windy Hollow Lake (swim beach, fishing, campground)br- 13 miles to Owensboro: entertainment, museums, restaurantsbr- 13 miles to Western Kentucky Botanical Gardenbr- 1 mile to Windy Hollow Speedwaybr- 84 miles to Mammoth Cave National Parkbr- 149 miles to Nashville International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 2max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 3 steps to enterbr- The wood-burning stove is not available for guest usebr- While guests can enjoy lake views on-site, the lake on the property is not accessiblebr- Your safety matters. This property features 1 exterior security camera on the front door facing the front entry. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion
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Bath 1

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Sleep 8

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Exceptional(4)

$517.7

/ Nightly
Private Vacation Home

Spacious Home with Heated Swimming Pool + Hot Tub + Event Room + SLEEPS 23

Owensboro, Kentucky, United States

Forget your worries in this spacious and serene outdoor oasis! Relax in the hot tub or go for a heated swim. Cook an amazing meal in the large kitchen. There are a lot of things to do in Owensboro including Friday After 5 event downtown, concerts, Green River Distillery, Smothers Water Park, Bluegrass Music Hall of Fame & Museum, Owensboro Museum of Science & History, Edge Ice Skating Center, Owensboro Museum of Fine Art, Malco Cinema + much more. Located only 40 minutes from Holiday World. Less than 1/2 mile from Golf Course. This home is very spacious with a great floor plan featuring 2 MASTER SUITES of the 4 bedrooms.brCLEAN & CLUTTER FREE! Pool is OPEN ALL YEAR & HEATED IN WINTER HOT TUB IS OPEN ALL YEAR.
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Bath 4

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Sleep 23

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$90.17

/ Nightly
Private Vacation Home

Comfy! Carmel Cottage Centrally Located

Owensboro, Kentucky, United States

Welcome to this newly renovated, single family brick home. Say goodbye to hotels and carpet and spread out in our comfy home!brbrYou will enjoy easy access to everything in Owensboro from this centrally located home just across the street from the Carmel Home.brbrWe offer a cozy, clean place to call your own during your stay with us. We’ll give you your space, but happy to help in any way we can. Just ask!brAmy & Jenny
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Sleep 4

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Exceptional(23)

$268.47

/ Nightly
Private Vacation Home

Downtown Dream in Owensboro Ky

Owensboro, Kentucky, United States

Just blocks from the Riverfront, this 1896 Victorian beauty has stood the test of time. Enjoy the best of both worlds with authentic, rich architecture offering just a hint of modern flare. This 4 Bedroom, 3 Bath home is suited for up to 12 guests and feels like your home away from home. Pamper yourself with a weekend getaway or make your lifelong dreams come true. Security cameras are on the front and back porch but they are not active they are inoperable.
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Sleep 12

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Very Good(1)

$378.48

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Private Vacation Home

Heated Swimming Pool + Hot Tub + Privacy

Owensboro, Kentucky, United States

Leave your worries behind! Relax in the hot tub, go for a swim all while enjoying the privacy of the fenced in backyard or cozy up with a book by the fireplace! There are a lot of things to do in Owensboro including Friday After 5 event downtown, concerts, Green River Distillery, Smothers Water Park, Bluegrass Music Hall of Fame & Museum, Owensboro Museum of Science & History, Edge Ice Skating Center, Owensboro Museum of Fine Art, Malco Cinema + much more. Located only 40 minutes from Holiday World. 2 minutes from Hillcrest Golf Course!
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Sleep 10

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Exceptional(19)

$214.16

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Private Vacation Home

Welcome to simple comfort a like new family friendly home Full of accommodation

Owensboro, Kentucky, United States

Rare opening! 4.99 STAR rating – we’re usually booked solid!brHi, this is Simple Comfort – fresh, modern, spotless home with high-end amenities & minimal clutter. Minutes from Holiday World, shopping, dining – great for families, work, or visits.brStocked kitchen w/ free snacks/coffee/spices, memory foam beds, glow-light recliners, fast Wi-Fi, Xbox, desk & spa-like bath.brSleeps 6. Reviews say it all!brNo pets/parties. Book fast – dates go quick!
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Exceptional(4)

$199.93

/ Nightly
Private Vacation Home

Center of city private Town Home W/fire pit &BBQ

Owensboro, Kentucky, United States

Welcome to Owensboro . Enjoy a stylish experience at this Touch of Grey Town Home nestled in the center of town . Stylish modern design and open living room concept is close to downtown regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, wine tasting , concerts on the river, festivals , nightlife and of coarse the Bluegrass Hall of Fame & Museum . Modern luxury design meets casual elegance.
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Exceptional(22)

$151.98

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Apartment

MILSuite separate entry...close to all things Owensboro and Daviess County.

Owensboro, Kentucky, United States

MIL suite with separate entry in wooded country setting. This is our home we live in. The suite adjoins our home but also has separate entrance. Suite separated from main home by two deadbolt locked doors. One bedroom, living room, small kitchen area and bathroom. Clean, cozy. No stove but hot plate, charcoal grill, microwave and air fryer provided. Fridge and freezer also. Shower stall in bathroom. Cozy, comfy queen bed. Blow up queen air mattress(2) also available. Baby playpen available upon request Outside area is over 5 acres and you're welcome to walk around and sit at the small pond or near the barn. Yard has trampoline for kids, above ground pool and basketball goal outside. NEW Deck outside suite perfect for overlooking the woods or grilling on provided charcoal grill. Quiet area. Very close to Yellow Creek Park and highway 54. Must walk around house on grass to entrance. Children must be supervised around pond or pool. Swim at own risk. For stays over one week, guests will need to supply own toilet paper and paper towels after starter supply runs out. NO smoking of anything. If you smoke, $200 fee non negotiable. We do have a inside dog on the property.
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Sleep 6

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Exceptional(22)

$193.24

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Private Vacation Home

Centrally Located Mid Century Traditional Home

Owensboro, Kentucky, United States

This recently renovated home is located minutes from Owensboro’s many sports venues and the downtown riverfront entertainment district and only 15 minutes from Yellow Creek Park, site of the annual International Bluegrass Music Hall of Fame and Museum’s annual ROMP music festival. brbrIt boasts four bedrooms (1-K, 1-Q, 2-T/T) on two floors to comfortably sleep 8, two full bathrooms (1-T/S, 1-S), a large fully equipped kitchen, a comfortable living room with gas fireplace, a dining room that can seat 6-10, and a basement with a TV area, a huge laundry area, and a ping pong table. brbrThe large yard provides off street parking and plenty of room to relax. An enclosed front porch and a patio round out the space. brbrWe were careful during the renovation to retain all of the original hardwood flooring and custom woodwork as well as the tiling and plasterwork. Updates such as LED lighting and stainless steel appliances alongside the mid century craftsmanship make for an instantly comfortable home during your time in Owensboro. brbrHigh speed WiFi and smart televisions allow you to enjoy your own streaming services. In keeping with our mid century origins, we can also receive local over-the-air broadcasts.
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Sleep 8

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Exceptional(2)

$501.94

/ Nightly
Private Vacation Home

Hot tub/pool/firepit/ 3 bedroom Home center of town 2 Livingroom's sleeps 12

Owensboro, Kentucky, United States

Hot Tub On Hill /SHORT 40 MIN DRIVE TO HOLIDAY WORLD SPLASHIN ' SAFARI . A very spacious vacation spot the whole group will enjoy! Easy access to everything and centrally located. Close to downtown, the regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, concerts on the river, festivals ,nightlife and sport facilities. Pool , hot tub, Fire-Pit with outdoor patio and BBQ with enough seating for 14 , GREAT for multiple families with two separate living areas. Let the house on Hill Make your family gatherings memorable.
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Sleep 12

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Exceptional(31)

$144.13

/ Nightly
Private Vacation Home

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Owensboro, Kentucky, United States

This uniquely remodeled Hill Ave. Home is the perfect home for your trip to Owensboro with 3 bedrooms, including 2 queen beds and 1 twin bed and a queen air bed in the den! We also have 2 nice twin portable mattresses that can be used as well! We have 1 full remodeled bath inside which has tub, shower with exhaust fan! We also have a seasonal outside bathroom that has a toilet and shower that works great for groups and people that have difficulty getting in and out of regular bathtubs! The outside bathroom goes great for using when there are several guest or challenged guest! It comes in handy when the inside bathroom is in use and gives you that natural feel of taking a shower outside! This welcoming property offers tremendous comfort for guests. The soothing ambiance of the living room and den featuring an additional queen air bed, provides a cozy space to relax after a day of exploring. Enjoy the amenities such as central air, WiFi, washer/dryer, dishwasher, toaster, and nuwave air fryer! Dishes, pots and pans, and utensils provided! Nice deck, grill, and table. We have a tv in the living room and den with ceiling fans! For more fun we have a pingpong table and multigame table, checkers and chess, cornhole or go across the street to the healthpark to swim, play basketball, use the walk track and use weight room or use sauna! The 1 bathroom, 1 with bath & shower to ensure that everyone can freshen up before heading out to enjoy the attractions and many tasty restaurants of Owensboro and enjoy our Hill Ave Home! The home is centrally located so you can quickly get to any part of town with grocery, gas station, hardware store and restaurants just a few blocks away! Everyone that has stayed in the Hill Ave. Home have loved it including one couple that just left this week got home and booked it again in 2 to 3 weeks! We now have a high chair to add to what we have to offer! We recently added a patio table and chairs out front for relaxing in and is the smoking area! The most common comments we get is this place is so nice and spacious! Our home is in an extremely safe area and has a privacy fence around the back for your safety and privacy! We have great pizza places as well as many other eating places such as Cracker Barrell, Chick filet, and we have a Jimmy Johns at the end of the street!
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Sleep 7

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Exceptional(18)

$272.34

/ Nightly
Private Vacation Home

Newly renovated- 2.5 mi to Downtown Riverfront

Owensboro, Kentucky, United States

The City House is a renovated 4 bed / 2.5 bath home in the heart of Owensboro. The convenient location makes it easy to get to restaurants, shopping, parks, downtown or sporting events. In less than 10 minutes, you can enjoy just about everything Owensboro has to offer whether it’s barbecue, bourbon or Bluegrass!
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Sleep 12

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$203.39

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Private Vacation Home

Center of City Private Townhome/courtyard /firepit 2 bed

Owensboro, Kentucky, United States

Enjoy a stylish experience at this Touch of Grey Town Home nestled in the center of town . This 2 bedroom Stylish modern design and open living room concept is close to downtown regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, wine tasting , concerts on the river, festivals , nightlife and of coarse the Bluegrass Hall of Fame & Museum . 10 min drive to all major medical facilities and the Owensboro Health Regional Hospital. Modern luxury design meets casual elegance. The perfect short-term rental for traveling professionals or families transitioning to the area. brAs licensed real estate agents in the area, the owners would love the opportunity to help you find the perfect permanent home while you stay with us. We have several furnished homes available .
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Sleep 4

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Exceptional(1)

$163.49

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Private Vacation Home

Cozy 2-bedroom house in a central location

Owensboro, Kentucky, United States

Get ready to relax in this 2-bedroom house. The space features two queen beds, perfect for a restful night’s sleep. Guests enjoy a lovely, cozy atmosphere with heating and AC to keep things comfortable year-round. The serene bathroom offers everything needed to refresh after a day of exploring. Whether you’re unwinding indoors or stepping out to enjoy the surroundings, this gorgeous house provides a peaceful retreat. Fall in love with the charm and comfort this home brings to your getaway.
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Sleep 4

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Exceptional(8)

$235.32

/ Nightly
Private Vacation Home

Charming 3-bedroom house with king bed , pet friendly

Owensboro, Kentucky, United States

Our Village gate is cozy and quaint yet strategically positioned in close proximity to community amenities, restaurants,shopping,and downtown area . A short distance to hop on the Greenbelt to enjoy a walk with your family .Also about 30 miles to Holiday World! Have fun with the whole family at this stylish place!Make yourself at home in this 3-bedroom Owensboro retreat. This pleasant house features 1 king bed, 1 queen bed, and 1 bunk bed, perfect for families or friends traveling together. We think our place will help you experience everything Owensboro has to offer.
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Sleep 6

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$174.86

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Private Vacation Home

Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.

Owensboro, Kentucky, United States

3 bedroom (5 beds), 2 full bathroom house with a yard. Outdoor dining area with a grill and fire pit.brHalf mile from Legion Park, a 22 acre space with playground, picnic shelters, basketball & tennis courts.2.9 miles from the Owensboro Riverfront with Smothers park named Top playground in the World, stunning fountains, restaurants, shopping and depending on the time of year activities and concerts. Also located riverfront is the Bluegrass Music Hall of Fame & Museum. brGuests will have access to entire house with keypad entry, front and back yards. Detached garage is for owners personal storage.brbrRoom in the yard for pitching and catching. Perfect for families traveling for ball games to practice.
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Sleep 6

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Exceptional(46)

$212.77

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Private Vacation Home

The Haven on Hill Ave

Owensboro, Kentucky, United States

This 4 bedroom, 2 bathroom home from the 1950s has recently been remodeled with unique accent touches, including hardwood floors, crown molding, and built-in cabinets. The quiet neighborhood is located on the Dogwood / Azalea Trail. It is centrally located in town. Nearby there are parks, shopping, restaurants, and the Riverpark center. The backyard is fully fenced to protect any four footed guests.
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Sleep 8

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Exceptional(8)

$155.01

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Country House

Charming 3 bedroom, 2 bath farmhouse just outside of Owensboro, KY

Owensboro, Kentucky, United States

Welcome to this charming farmhouse just outside of Owensboro, KY. This property offers 3 cozy bedrooms with a king, queen, two twin beds, perfect for a tranquil night's sleep. With 2 full bathrooms, guests can freshen up before exploring the city or heading to visit family or friends. There is a walk-in shower in the master bathroom and a tub/shower in the other bathroom. The house also features an equipped kitchen, dining area and a comfortable living area. The house is one level with no steps to enter. Enjoy your time in Owensboro at our farmhouse.
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Sleep 6

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Exceptional(19)

$168.61

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Condo

Downtown condo Cozy 2-bedroom with plenty of space

Owensboro, Kentucky, United States

Welcome to our downtown historical building with newly renovated 2700 square foot second floor condo, perfect for your getaway! This spacious retreat boasts a large living room, two inviting bedrooms, and two additional fold-out couches for ultimate comfort.brWith 1.5 baths, a spacious kitchen no stove,and a dedicated gaming area featuring basketball and board games, as well as a space for guitar enthusiasts, your stay promises relaxation and entertainment.
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$607.05

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Private Vacation Home

Luxury 1920's 6-bedroom home centrally located in Owensboro

Owensboro, Kentucky, United States

Discover the beauty of Owensboro from this fabulous 6-bedroom home! With 3 bathrooms, including a relaxing clawfoot tub, guests find plenty of space to unwind. The bedrooms feature a mix of 2 king beds, 3 queen beds, 2 full bed, and 2 sofa beds, perfect for groups of all sizes. Enjoy a comfortable stay with heating (radiant heat when temperatures are below 30 degrees) andAC. Whether you’re gathering in the spacious living areas or resting in our cozy rooms, this luxury home offers a welcoming retreat. Experience what Owensboro has to offer with a stay at our excellent house.
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Bath 3

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Sleep 18

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Home Most popular vacation rentals in Owensboro

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$517.70

/ Nightly
Private vacation home

Spacious Home with Heated Swimming Pool + Hot Tub + Event Room + SLEEPS 23

Owensboro, Kentucky, United States

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Bath 4

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Sleep 23

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$94.49

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Private vacation home

Cozy, Furnished Corporate Rental

Owensboro, Kentucky, United States

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Sleep 2

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$132.70

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Apartment

Private 2 bdrm apartment in the heart of the city. Pet friendly.

Owensboro, Kentucky, United States

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Sleep 6

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$160.90

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Private vacation home

Cozy Cottage home

Owensboro, Kentucky, United States

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Sleep 6

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$184.73

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Private vacation home

1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro, Kentucky, United States

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Sleep 4

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$193.24

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Private vacation home

Centrally Located Mid Century Traditional Home

Owensboro, Kentucky, United States

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Sleep 8

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$199.93

/ Nightly
Private vacation home

Center of city private Town Home W/fire pit &BBQ

Owensboro, Kentucky, United States

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Sleep 4

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$212.77

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Private vacation home

The Haven on Hill Ave

Owensboro, Kentucky, United States

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Sleep 8

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$365.21

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Private vacation home

Cozy Stylish 2 BR Home w/ Pool / Relax & Enjoy

Owensboro, Kentucky, United States

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Bath 2

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Sleep 6

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$298.41

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Private vacation home

315 West 14th Street

Owensboro, Kentucky, United States

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Bath 2

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Sleep 8

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Most Popular Cities in Kentucky