Vacation rentals in Highland Hills, OH

Best Vacation rentals and Airbnb offers in Highland Hills, OH

Rock & Roll Suite CLE - 1 Bedroom / 1 bathroom near Downtown Cleveland, OH

Apartment, Highland Hills

Rock & Roll Suite CLE - 1 Bedroom / 1 bathroom near Downtown Cleveland, OH is a apartment in Highland Hills, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Rock & Roll Suite CLE - 1 Bedroom / 1 bathroom near Downtown Cleveland, OH

Rock & Roll Suite CLE - 1 Bedroom / 1 bathroom near Downtown Cleveland, OH is a apartment in Highland Hills, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$76/night

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Cozy Stone Castle 12 Mins To CWRU/Cleveland Clinic

Apartment, Highland Hills

Cozy Stone Castle 12 Mins To CWRU/Cleveland Clinic is a apartment in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Stone Castle 12 Mins To CWRU/Cleveland Clinic

Cozy Stone Castle 12 Mins To CWRU/Cleveland Clinic is a apartment in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $798.

From$85/night

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Great little house in Woodmere/Beachwood, Orange

Holiday Home, Highland Hills

Great little house in Woodmere/Beachwood, Orange is a holiday home in Highland Hills, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Great little house in Woodmere/Beachwood, Orange

Great little house in Woodmere/Beachwood, Orange is a holiday home in Highland Hills, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $865.

From$86/night

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Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Holiday Home, Highland Hills

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch! is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch! is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $822.

From$88/night

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Browse Vacation Rentals with a Pool in Highland Hills, OH

Add a pool to the search when you want an easy place to cool off between outings.

Deck, Pool Table! Walkable Cleveland Heights Apt

Apartment, Highland Hills

Deck, Pool Table! Walkable Cleveland Heights Apt is a apartment in Highland Hills, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Deck, Pool Table! Walkable Cleveland Heights Apt

Deck, Pool Table! Walkable Cleveland Heights Apt is a apartment in Highland Hills, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$115/night

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Queen Studio | 24-Hour Business Center, Fitness Center + Free Daily Breakfast

Apartment, Highland Hills

Queen Studio · 24-Hour Business Center, Fitness Center + Free Daily Breakfast is a apartment in Highland Hills, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Queen Studio | 24-Hour Business Center, Fitness Center + Free Daily Breakfast

Queen Studio · 24-Hour Business Center, Fitness Center + Free Daily Breakfast is a apartment in Highland Hills, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$126/night

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Spacious Queen Studio | 24-Hour Business Center, Fitness Center + Free Daily Breakfast

Apartment, Highland Hills

Spacious Queen Studio · 24-Hour Business Center, Fitness Center + Free Daily Breakfast is a apartment in Highland Hills, with pool access and kitchen access. This stay gives travelers a…

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About Spacious Queen Studio | 24-Hour Business Center, Fitness Center + Free Daily Breakfast

Spacious Queen Studio · 24-Hour Business Center, Fitness Center + Free Daily Breakfast is a apartment in Highland Hills, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,131.

From$126/night

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Free Breakfast + 24-Hour Business Center + Gym

Condo, Highland Hills

Free Breakfast + 24-Hour Business Center + Gym is a condo in Highland Hills, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Free Breakfast + 24-Hour Business Center + Gym

Free Breakfast + 24-Hour Business Center + Gym is a condo in Highland Hills, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,211.

From$133/night

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Best Highland Hills, OH vacation rentals with parking

Find vacation rentals that make arriving by car easier.

8 Mi to Dtwn CLE: Cozy Couple's Retreat w/ Gym!

Apartment, Highland Hills

8 Mi to Dtwn CLE: Cozy Couple's Retreat w/ Gym! is a apartment in Highland Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About 8 Mi to Dtwn CLE: Cozy Couple's Retreat w/ Gym!

8 Mi to Dtwn CLE: Cozy Couple's Retreat w/ Gym! is a apartment in Highland Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,032.

From$97/night

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The Lodge-Cozy 4 BdRm home w/step-in shower close to CCF/UH, universities n more

Holiday Home, Highland Hills

The Lodge-Cozy 4 BdRm home w/step-in shower close to CCF/UH, universities n more is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a…

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About The Lodge-Cozy 4 BdRm home w/step-in shower close to CCF/UH, universities n more

The Lodge-Cozy 4 BdRm home w/step-in shower close to CCF/UH, universities n more is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,057.

From$111/night

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Bright & Peaceful | 2BDR w/ Patio | CLE Clinic

Apartment, Highland Hills

Bright & Peaceful · 2BDR w/ Patio · CLE Clinic is a apartment in Highland Hills, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Bright & Peaceful | 2BDR w/ Patio | CLE Clinic

Bright & Peaceful · 2BDR w/ Patio · CLE Clinic is a apartment in Highland Hills, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,123.

From$117/night

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Charming 2BR Top Floor Retreat Near Cleveland Clinic & Downtown

Apartment, Highland Hills

Charming 2BR Top Floor Retreat Near Cleveland Clinic & Downtown is a apartment in Highland Hills, with parking, room for a group, and a quieter setting. This stay gives travelers a…

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About Charming 2BR Top Floor Retreat Near Cleveland Clinic & Downtown

Charming 2BR Top Floor Retreat Near Cleveland Clinic & Downtown is a apartment in Highland Hills, with parking, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,090.

From$126/night

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Best Pet-Friendly Vacation Rentals in Highland Hills, OH

Bring your pet along with stays that welcome four-legged travelers.

Experience a home near Cleveland Clinic & parks

Apartment, Highland Hills

Experience a home near Cleveland Clinic & parks is a apartment in Highland Hills, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Experience a home near Cleveland Clinic & parks

Experience a home near Cleveland Clinic & parks is a apartment in Highland Hills, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $750.

From$81/night

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Little Italy · Group Stay · 4 TV's · Pet Friendly

Apartment, Highland Hills

Little Italy · Group Stay · 4 TV's · Pet Friendly is a apartment in Highland Hills, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Little Italy · Group Stay · 4 TV's · Pet Friendly

Little Italy · Group Stay · 4 TV's · Pet Friendly is a apartment in Highland Hills, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,022.

From$110/night

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Walk to Dining, Bars & Transit!

Holiday Home, Highland Hills

Walk to Dining, Bars & Transit! is a holiday home in Highland Hills, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Walk to Dining, Bars & Transit!

Walk to Dining, Bars & Transit! is a holiday home in Highland Hills, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$121/night

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Delightful 5-bedroom house with FREE two- car garage parking.

Holiday Home, Highland Hills

Delightful 5-bedroom house with FREE two- car garage parking. is a holiday home in Highland Hills, with pet-friendly space, parking, and room for a group. This stay gives travelers a…

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About Delightful 5-bedroom house with FREE two- car garage parking.

Delightful 5-bedroom house with FREE two- car garage parking. is a holiday home in Highland Hills, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,252.

From$141/night

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Best Highland Hills, OH vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

4 Mi to Dtwn: Modern Retreat w/ Yard in Cleveland

Holiday Home, Highland Hills

4 Mi to Dtwn: Modern Retreat w/ Yard in Cleveland is a holiday home in Highland Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About 4 Mi to Dtwn: Modern Retreat w/ Yard in Cleveland

4 Mi to Dtwn: Modern Retreat w/ Yard in Cleveland is a holiday home in Highland Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,239.

From$98/night

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Charming 2-bedroom house with AC in Cleveland

Holiday Home, Highland Hills

Charming 2-bedroom house with AC in Cleveland is a holiday home in Highland Hills, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom house with AC in Cleveland

Charming 2-bedroom house with AC in Cleveland is a holiday home in Highland Hills, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $947.

From$116/night

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Shade of Love I Adult Themed Escape

Holiday Home, Highland Hills

Shade of Love I Adult Themed Escape is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Shade of Love I Adult Themed Escape

Shade of Love I Adult Themed Escape is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,443.

From$132/night

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'The Maple Tree' Home: 14 Mi to Downtown Cleveland

Holiday Home, Highland Hills

'The Maple Tree' Home: 14 Mi to Downtown Cleveland is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 'The Maple Tree' Home: 14 Mi to Downtown Cleveland

'The Maple Tree' Home: 14 Mi to Downtown Cleveland is a holiday home in Highland Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,766.

From$148/night

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Our Favorite Family-Friendly Vacation Rentals in Highland Hills, OH

Plan a trip with stays that give families more room to spread out.

Charming Stone Cottage--20 min to CCF/CWRU/UH

Holiday Home, Highland Hills

Charming Stone Cottage--20 min to CCF/CWRU/UH is a holiday home in Highland Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming Stone Cottage--20 min to CCF/CWRU/UH

Charming Stone Cottage--20 min to CCF/CWRU/UH is a holiday home in Highland Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,068.

From$111/night

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A nice and cozy house in Cle surbs. Quiet neighborhood. Permit 154.

Holiday Home, Highland Hills

A nice and cozy house in Cle surbs. Quiet neighborhood. Permit 154. is a holiday home in Highland Hills, with kitchen access and a quieter setting. This stay gives travelers a comfortable…

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About A nice and cozy house in Cle surbs. Quiet neighborhood. Permit 154.

A nice and cozy house in Cle surbs. Quiet neighborhood. Permit 154. is a holiday home in Highland Hills, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,094.

From$123/night

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Home-like family-size and efficient. A business travelers' dream.

Holiday Home, Highland Hills

Home-like family-size and efficient. A business travelers' dream. is a holiday home in Highland Hills, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Home-like family-size and efficient. A business travelers' dream.

Home-like family-size and efficient. A business travelers' dream. is a holiday home in Highland Hills, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$132/night

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Cozy, Upstairs Apartment Pets Welcome with fee Family Friendly Close to Everything

Apartment, Highland Hills

Cozy, Upstairs Apartment Pets Welcome with fee Family Friendly Close to Everything is a apartment in Highland Hills, with pet-friendly space, parking, and room for a group. This stay gives…

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About Cozy, Upstairs Apartment Pets Welcome with fee Family Friendly Close to Everything

Cozy, Upstairs Apartment Pets Welcome with fee Family Friendly Close to Everything is a apartment in Highland Hills, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,329.

From$133/night

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