Vacation rentals in Highlands Reserve, FL

Best Vacation rentals and Airbnb offers in Highlands Reserve, FL

Super comodo y acogedor studio cerca a Disney.

Apartment, Highlands Reserve

Super comodo y acogedor studio cerca a Disney. is a apartment in Highlands Reserve, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Super comodo y acogedor studio cerca a Disney.

Super comodo y acogedor studio cerca a Disney. is a apartment in Highlands Reserve, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $487.

From$54/night

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Amazing Fully Renovated 4 Bedroom Very Close to the Pool and Clubhouse

Holiday Home, Highlands Reserve

Amazing Fully Renovated 4 Bedroom Very Close to the Pool and Clubhouse is a holiday home in Highlands Reserve, with pool access and room for a group. This stay gives travelers a comfortable…

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About Amazing Fully Renovated 4 Bedroom Very Close to the Pool and Clubhouse

Amazing Fully Renovated 4 Bedroom Very Close to the Pool and Clubhouse is a holiday home in Highlands Reserve, with pool 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: gym, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $895.

From$77/night

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Peaceful retreat - 4 bed Pool & Spa Home

Villa, Highlands Reserve

Peaceful retreat - 4 bed Pool & Spa Home is a villa in Highlands Reserve, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Peaceful retreat - 4 bed Pool & Spa Home

Peaceful retreat - 4 bed Pool & Spa Home is a villa in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $982.

From$91/night

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Fairway Escape – 4BR Highlands Reserve Villa with Private Pool Near Disney

Villa, Highlands Reserve

Fairway Escape – 4BR Highlands Reserve Villa with Private Pool Near Disney is a villa in Highlands Reserve, with pool access and room for a group. This stay gives travelers a comfortable…

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About Fairway Escape – 4BR Highlands Reserve Villa with Private Pool Near Disney

Fairway Escape – 4BR Highlands Reserve Villa with Private Pool Near Disney is a villa in Highlands Reserve, with pool 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $892.

From$92/night

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Browse Vacation Rentals with a Pool in Highlands Reserve, FL

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

4 beds pool and spa home with game room Calabay

Villa, Highlands Reserve

4 beds pool and spa home with game room Calabay is a villa in Highlands Reserve, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About 4 beds pool and spa home with game room Calabay

4 beds pool and spa home with game room Calabay is a villa in Highlands Reserve, with pool access, 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: free cancellation, pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,070.

From$114/night

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Three Palms - Luxury Villa in Calabay Parc with 4 Bedrooms and 3 Bathrooms

Holiday Home, Highlands Reserve

Three Palms - Luxury Villa in Calabay Parc with 4 Bedrooms and 3 Bathrooms is a holiday home in Highlands Reserve, with pool access, easy beach access, and kitchen access. This stay gives…

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About Three Palms - Luxury Villa in Calabay Parc with 4 Bedrooms and 3 Bathrooms

Three Palms - Luxury Villa in Calabay Parc with 4 Bedrooms and 3 Bathrooms is a holiday home in Highlands Reserve, with pool access, easy beach 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,429.

From$124/night

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Spacious 5 bedroom home in Highlands Reserve near Disneyworld!

Holiday Home, Highlands Reserve

Spacious 5 bedroom home in Highlands Reserve near Disneyworld! is a holiday home in Highlands Reserve, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Spacious 5 bedroom home in Highlands Reserve near Disneyworld!

Spacious 5 bedroom home in Highlands Reserve near Disneyworld! is a holiday home in Highlands Reserve, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,391.

From$138/night

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Golf Course View Villa! Just 25 mins to Disney Magic

Villa, Highlands Reserve

Golf Course View Villa! Just 25 mins to Disney Magic is a villa in Highlands Reserve, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Golf Course View Villa! Just 25 mins to Disney Magic

Golf Course View Villa! Just 25 mins to Disney Magic is a villa in Highlands Reserve, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,435.

From$145/night

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Best Highlands Reserve, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

13 Mi to Animal Kingdom: Getaway w/ Patio!

Holiday Home, Highlands Reserve

13 Mi to Animal Kingdom: Getaway w/ Patio! is a holiday home in Highlands Reserve, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About 13 Mi to Animal Kingdom: Getaway w/ Patio!

13 Mi to Animal Kingdom: Getaway w/ Patio! is a holiday home in Highlands Reserve, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,219.

From$89/night

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Davenport - Four Corners House Near Orlando Theme Parks

Holiday Home, Highlands Reserve

Davenport - Four Corners House Near Orlando Theme Parks is a holiday home in Highlands Reserve, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Davenport - Four Corners House Near Orlando Theme Parks

Davenport - Four Corners House Near Orlando Theme Parks is a holiday home in Highlands Reserve, 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 $1,137.

From$113/night

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Charming 4 BR Home with Private Pool & Office/5BR

Villa, Highlands Reserve

Charming 4 BR Home with Private Pool & Office/5BR is a villa in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming 4 BR Home with Private Pool & Office/5BR

Charming 4 BR Home with Private Pool & Office/5BR is a villa in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,786.

From$151/night

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EV_536 - 4 Bed 2 Bath Home with Screened-In Pool

Villa, Highlands Reserve

EV_536 - 4 Bed 2 Bath Home with Screened-In Pool is a villa in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About EV_536 - 4 Bed 2 Bath Home with Screened-In Pool

EV_536 - 4 Bed 2 Bath Home with Screened-In Pool is a villa in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,808.

From$156/night

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Best Pet-Friendly Vacation Rentals in Highlands Reserve, FL

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

Happy Daze - Home for 8

Holiday Home, Highlands Reserve

Happy Daze - Home for 8 is a holiday home in Highlands Reserve, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Happy Daze - Home for 8

Happy Daze - Home for 8 is a holiday home in Highlands Reserve, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $990.

From$80/night

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4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!!

Holiday Home, Highlands Reserve

4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!! is a holiday home in Highlands Reserve, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About 4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!!

4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!! is a holiday home in Highlands Reserve, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,193.

From$97/night

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Champions Gate Area Private Pool Villa w/ AC Game Room, Play Ground and Basketball Court– Minutes to Disney & Orlando Fun

Holiday Home, Highlands Reserve

Champions Gate Area Private Pool Villa w/ AC Game Room, Play Ground and Basketball Court– Minutes to Disney & Orlando Fun is a holiday home in Highlands Reserve, with pet-friendly space,…

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About Champions Gate Area Private Pool Villa w/ AC Game Room, Play Ground and Basketball Court– Minutes to Disney & Orlando Fun

Champions Gate Area Private Pool Villa w/ AC Game Room, Play Ground and Basketball Court– Minutes to Disney & Orlando Fun is a holiday home in Highlands Reserve, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,251.

From$144/night

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361 Amazing Place for Your Orlando Vacation

Holiday Home, Highlands Reserve

361 Amazing Place for Your Orlando Vacation is a holiday home in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 361 Amazing Place for Your Orlando Vacation

361 Amazing Place for Your Orlando Vacation is a holiday home in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,685.

From$180/night

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Best Highlands Reserve, FL vacation rentals with a kitchen

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

Disney Four Corners nice 3 Bedroom Villa !

Holiday Home, Highlands Reserve

Disney Four Corners nice 3 Bedroom Villa ! is a holiday home in Highlands Reserve, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Disney Four Corners nice 3 Bedroom Villa !

Disney Four Corners nice 3 Bedroom Villa ! is a holiday home in Highlands Reserve, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,242.

From$114/night

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Disney Sunshine Villa: Private Screened Pool & Modern 4BR

Holiday Home, Highlands Reserve

Disney Sunshine Villa: Private Screened Pool & Modern 4BR is a holiday home in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Disney Sunshine Villa: Private Screened Pool & Modern 4BR

Disney Sunshine Villa: Private Screened Pool & Modern 4BR is a holiday home in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,411.

From$124/night

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Beautiful One level Pool Home on Golf Resort

Holiday Home, Highlands Reserve

Beautiful One level Pool Home on Golf Resort is a holiday home in Highlands Reserve, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful One level Pool Home on Golf Resort

Beautiful One level Pool Home on Golf Resort is a holiday home in Highlands Reserve, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,921.

From$155/night

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3 Bed Golf Community Villa with private pool overlooking Golf Course

Holiday Home, Highlands Reserve

3 Bed Golf Community Villa with private pool overlooking Golf Course is a holiday home in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a…

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About 3 Bed Golf Community Villa with private pool overlooking Golf Course

3 Bed Golf Community Villa with private pool overlooking Golf Course is a holiday home in Highlands Reserve, with pool access, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,650.

From$159/night

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Our Favorite Family-Friendly Vacation Rentals in Highlands Reserve, FL

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

Come, enjoy our spacious and relaxing backyard.

Holiday Home, Highlands Reserve

Come, enjoy our spacious and relaxing backyard. is a holiday home in Highlands Reserve, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Come, enjoy our spacious and relaxing backyard.

Come, enjoy our spacious and relaxing backyard. is a holiday home in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,200.

From$114/night

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Near Disney - 4BR Family Retreat w/ Private Pool, Spa & Game Room

Holiday Home, Highlands Reserve

Near Disney - 4BR Family Retreat w/ Private Pool, Spa & Game Room is a holiday home in Highlands Reserve, with pool access, room for a group, and a quieter setting. This stay gives…

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About Near Disney - 4BR Family Retreat w/ Private Pool, Spa & Game Room

Near Disney - 4BR Family Retreat w/ Private Pool, Spa & Game Room is a holiday home in Highlands Reserve, with pool access, 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,454.

From$138/night

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Calabay Parc - Spacious 4 bed to suit your family vacation

Holiday Home, Highlands Reserve

Calabay Parc - Spacious 4 bed to suit your family vacation is a holiday home in Highlands Reserve, with pool access, easy beach access, and parking. This stay gives travelers a comfortable…

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About Calabay Parc - Spacious 4 bed to suit your family vacation

Calabay Parc - Spacious 4 bed to suit your family vacation is a holiday home in Highlands Reserve, with pool access, 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: free cancellation, pool, kitchen, with kitchen, and parking.

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

From$139/night

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Enjoy Serenity by the Pool! VALUE! Family Memories Made!

Holiday Home, Highlands Reserve

Enjoy Serenity by the Pool! VALUE! Family Memories Made! is a holiday home in Highlands Reserve, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Enjoy Serenity by the Pool! VALUE! Family Memories Made!

Enjoy Serenity by the Pool! VALUE! Family Memories Made! is a holiday home in Highlands Reserve, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,965.

From$170/night

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