Vacation rentals in Highland, IL

Best Vacation rentals and Airbnb offers in Highland, IL

1 bed duplex near downtown Belleville next to heart garden and long story coffee

Holiday Home, Highland

1 bed duplex near downtown Belleville next to heart garden and long story coffee is a holiday home in Highland, with pet-friendly space. This stay gives travelers a comfortable base for…

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About 1 bed duplex near downtown Belleville next to heart garden and long story coffee

1 bed duplex near downtown Belleville next to heart garden and long story coffee is a holiday home in Highland, 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, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $614.

From$64/night

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Countryside Private Guest Room

Holiday Home, Highland

Countryside Private Guest Room is a holiday home in Highland. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Countryside Private Guest Room

Countryside Private Guest Room is a holiday home in Highland. 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, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $564.

From$68/night

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Perfect 1-bedroom apartment with in welcoming Belleville

Apartment, Highland

Perfect 1-bedroom apartment with in welcoming Belleville is a apartment in Highland, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

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About Perfect 1-bedroom apartment with in welcoming Belleville

Perfect 1-bedroom apartment with in welcoming Belleville is a apartment in Highland, with pet-friendly space 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $657.

From$69/night

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Guest suite in belleville

Apartment, Highland

Guest suite in belleville is a apartment in Highland. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Guest suite in belleville

Guest suite in belleville is a apartment in Highland. 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 $717.

From$75/night

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Best Highland, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Renovated Townhome w/ Garage, 12 Mi to St Louis

Holiday Home, Highland

Renovated Townhome w/ Garage, 12 Mi to St Louis is a holiday home in Highland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Renovated Townhome w/ Garage, 12 Mi to St Louis

Renovated Townhome w/ Garage, 12 Mi to St Louis is a holiday home in Highland, 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 $1,668.

From$143/night

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The Beaumont Suite !

Holiday Home, Highland

The Beaumont Suite ! is a holiday home in Highland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Beaumont Suite !

The Beaumont Suite ! is a holiday home in Highland, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,433.

From$148/night

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Sunset Cottage - 2 King beds! Downtown Glen Carbon

Holiday Home, Highland

Sunset Cottage - 2 King beds! Downtown Glen Carbon is a holiday home in Highland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sunset Cottage - 2 King beds! Downtown Glen Carbon

Sunset Cottage - 2 King beds! Downtown Glen Carbon is a holiday home in Highland, 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 $1,488.

From$149/night

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12 Mi to Dtwn St Louis: Family Home w/ Fireplaces!

Holiday Home, Highland

12 Mi to Dtwn St Louis: Family Home w/ Fireplaces! is a holiday home in Highland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 12 Mi to Dtwn St Louis: Family Home w/ Fireplaces!

12 Mi to Dtwn St Louis: Family Home w/ Fireplaces! is a holiday home in Highland, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,950.

From$164/night

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Best Pet-Friendly Vacation Rentals in Highland, IL

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

Charming apartment with nice fire pit for relaxing nights

Apartment, Highland

Charming apartment with nice fire pit for relaxing nights is a apartment in Highland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Charming apartment with nice fire pit for relaxing nights

Charming apartment with nice fire pit for relaxing nights is a apartment in Highland, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $932.

From$97/night

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Landmark, accessible home in the heart of Belleville’s historic downtown

Holiday Home, Highland

Landmark, accessible home in the heart of Belleville’s historic downtown is a holiday home in Highland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Landmark, accessible home in the heart of Belleville’s historic downtown

Landmark, accessible home in the heart of Belleville’s historic downtown is a holiday home in Highland, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,360.

From$149/night

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3 Bedroom, full kitchen and remodeled bathroom. Water-views from the Kitchen and covered deck.

Apartment, Highland

3 Bedroom, full kitchen and remodeled bathroom. Water-views from the Kitchen and covered deck. is a apartment in Highland, with pet-friendly space, outdoor space, and kitchen access. This…

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About 3 Bedroom, full kitchen and remodeled bathroom. Water-views from the Kitchen and covered deck.

3 Bedroom, full kitchen and remodeled bathroom. Water-views from the Kitchen and covered deck. is a apartment in Highland, with pet-friendly space, outdoor 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,472.

From$155/night

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Best Highland, IL vacation rentals with a kitchen

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

Carlyle lake home!

Holiday Home, Highland

Carlyle lake home! is a holiday home in Highland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Carlyle lake home!

Carlyle lake home! is a holiday home in Highland, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,560.

From$183/night

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Historic 4-bedroom house in Glen Carbon with AC

Holiday Home, Highland

Historic 4-bedroom house in Glen Carbon with AC is a holiday home in Highland, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Historic 4-bedroom house in Glen Carbon with AC

Historic 4-bedroom house in Glen Carbon with AC is a holiday home in Highland, with 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, hot tub, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,925.

From$185/night

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Renovated Townhome w/ Garage, 12 Mi to St Louis

Apartment, Highland

Renovated Townhome w/ Garage, 12 Mi to St Louis is a apartment in Highland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Renovated Townhome w/ Garage, 12 Mi to St Louis

Renovated Townhome w/ Garage, 12 Mi to St Louis is a apartment in Highland, 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 $1,736.

From$187/night

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The Beaumont Retreat

Holiday Home, Highland

The Beaumont Retreat is a holiday home in Highland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Beaumont Retreat

The Beaumont Retreat is a holiday home in Highland, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,762.

From$191/night

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Our Favorite Family-Friendly Vacation Rentals in Highland, IL

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

Travel Nurse Haven - Near 8 Hospitals - Sleeps 4

Apartment, Highland

Travel Nurse Haven - Near 8 Hospitals - Sleeps 4 is a apartment in Highland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Travel Nurse Haven - Near 8 Hospitals - Sleeps 4

Travel Nurse Haven - Near 8 Hospitals - Sleeps 4 is a apartment in Highland, 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,133.

From$120/night

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Experience Belleville in a 2 BR cozy home with a STL Cardinals theme.

Holiday Home, Highland

Experience Belleville in a 2 BR cozy home with a STL Cardinals theme. is a holiday home in Highland, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Experience Belleville in a 2 BR cozy home with a STL Cardinals theme.

Experience Belleville in a 2 BR cozy home with a STL Cardinals theme. is a holiday home in Highland, with 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,176.

From$124/night

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Skyline - Military/Family Friendly

Holiday Home, Highland

Skyline - Military/Family Friendly is a holiday home in Highland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Skyline - Military/Family Friendly

Skyline - Military/Family Friendly is a holiday home in Highland, 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 $1,276.

From$138/night

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The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

Apartment, Highland

The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB is a apartment in Highland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB is a apartment in Highland, 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 $1,293.

From$141/night

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