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Oak Orchard Holiday Rentals

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50 rentals in Oak Orchard.
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Vacationing at Peninsula Resort, Indian River, DE, holiday rental in Oak Orchard

Vacationing at Peninsula Resort, Indian River, DE

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Unit 4305 - Lovely third floor condo in the Peninsula, holiday rental in Oak Orchard

Unit 4305 - Lovely third floor condo in the Peninsula

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unit 3102 - Close to the Peninsula pools and amenities!, holiday rental in Oak Orchard

Unit 3102 - Close to the Peninsula pools and amenities!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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27570 S Nicklaus - Beautiful five bedroom home in The Peninsula!, holiday rental in Oak Orchard

27570 S Nicklaus - Beautiful five bedroom home in The Peninsula!

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Cute Millsboro Home w/Sauna & Steam Room-Near Bay, holiday rental in Oak Orchard

Cute Millsboro Home w/Sauna & Steam Room-Near Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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27229 Barefoot - Beautifully furnished 5 bedroom home in The Peninsula!, holiday rental in Oak Orchard

27229 Barefoot - Beautifully furnished 5 bedroom home in The Peninsula!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Dagsboro Home w/View, 3-Min Walk to Bay Beach, holiday rental in Oak Orchard

Dagsboro Home w/View, 3-Min Walk to Bay Beach

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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5 br, 3.5 ba, sleeps 16, holiday rental in Oak Orchard

5 br, 3.5 ba, sleeps 16

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Unit 6301 - Windswept condo close to Lakeside Village in The Peninsula!, holiday rental in Oak Orchard

Unit 6301 - Windswept condo close to Lakeside Village in The Peninsula!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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33105 Serenity - Large home in the amenity rich Peninsula with Community Pool an, holiday rental in Oak Orchard

33105 Serenity - Large home in the amenity rich Peninsula with Community Pool an

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Stunning Millsboro Getaway: Yard + Game Room!, holiday rental in Oak Orchard

NEW! Stunning Millsboro Getaway: Yard + Game Room!

1 bedroom
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Peninsula Condo w/ Balcony & Resort Perks!, holiday rental in Oak Orchard

NEW! Peninsula Condo w/ Balcony & Resort Perks!

1 bedroom
3 bathrooms
Sleeps 8
Match: Sleeps
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Welcome to the most well-appointed rental in The Peninsula five star resort!, holiday rental in Oak Orchard

Welcome to the most well-appointed rental in The Peninsula five star resort!

3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Back on the rental market ! Bethany Bay Relaxation Awaits, holiday rental in Oak Orchard

Back on the rental market ! Bethany Bay Relaxation Awaits

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous 6 Bedroom House Overlooking Golf Course And Water.  Sleeps 19!, holiday rental in Oak Orchard

Gorgeous 6 Bedroom House Overlooking Golf Course And Water. Sleeps 19!

6 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
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Beautiful Home On 3rd Fairway In Peninsula Community, holiday rental in Oak Orchard

Beautiful Home On 3rd Fairway In Peninsula Community

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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** Pet friendly, awesome water views Bethany Bay - ENHANCED CLEAN/DISINFECTING, holiday rental in Oak Orchard

** Pet friendly, awesome water views Bethany Bay - ENHANCED CLEAN/DISINFECTING

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous 5 BR 4.5 BA - Bay Forest Villa Just Minutes from Bethany Beach (2020), holiday rental in Oak Orchard

Gorgeous 5 BR 4.5 BA - Bay Forest Villa Just Minutes from Bethany Beach (2020)

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Vacation Villa, holiday rental in Oak Orchard

Spacious Vacation Villa

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Beach Getaway, holiday rental in Oak Orchard

Charming Beach Getaway

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 Bed, 3 Bath Single Family Home with Pond View in Amenity Rich Bay Forest!, holiday rental in Oak Orchard

5 Bed, 3 Bath Single Family Home with Pond View in Amenity Rich Bay Forest!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stay in this 4BR Family Home/4 Private Baths. Great location! Stunning views!, holiday rental in Oak Orchard

Stay in this 4BR Family Home/4 Private Baths. Great location! Stunning views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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SEA-RENITY NOW! Large, family-friendly home in a Bethany Beach Golf Community, holiday rental in Oak Orchard

SEA-RENITY NOW! Large, family-friendly home in a Bethany Beach Golf Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Custom Decorated 5 Bedroom 4.5 Bath Luxury Resort Villa Minutes to Bethany Beach, holiday rental in Oak Orchard

Custom Decorated 5 Bedroom 4.5 Bath Luxury Resort Villa Minutes to Bethany Beach

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy Beautiful Bethany Beach, Surrounding Coastal Areas, Recreational Amenities, holiday rental in Oak Orchard

Enjoy Beautiful Bethany Beach, Surrounding Coastal Areas, Recreational Amenities

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Only Single Family Waterfront  Home  Rental in Bay Forest !, holiday rental in Oak Orchard

Only Single Family Waterfront Home Rental in Bay Forest !

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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VIEWS, VIEWS, VIEWS - First Floor Corner Unit Condo near Bethany Beach DE, holiday rental in Oak Orchard

VIEWS, VIEWS, VIEWS - First Floor Corner Unit Condo near Bethany Beach DE

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEST Location in BAY FOREST - Bethany Beach Villa, holiday rental in Oak Orchard

BEST Location in BAY FOREST - Bethany Beach Villa

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Peninsula- 5 Star Resort-Townhome (Near Rehoboth), holiday rental in Oak Orchard

The Peninsula- 5 Star Resort-Townhome (Near Rehoboth)

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Escape!  Perfect Location And Abundant Amenities In 4BR Condo In Bethany Bay!, holiday rental in Oak Orchard

Escape!  Perfect Location And Abundant Amenities In 4BR Condo In Bethany Bay!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy, bright and spacious new villa in The Peninsula- 5 star gated community, holiday rental in Oak Orchard

Cozy, bright and spacious new villa in The Peninsula- 5 star gated community

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Fabulous Bay Front View in Bethany Bay, holiday rental in Oak Orchard

Fabulous Bay Front View in Bethany Bay

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Minutes from Bethany Beach Boardwalk!, holiday rental in Oak Orchard

Minutes from Bethany Beach Boardwalk!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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2 story condo w/ Stunning, Panoramic, Waterfront Views!, holiday rental in Oak Orchard

2 story condo w/ Stunning, Panoramic, Waterfront Views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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24220 Canoe - New end unit townhome in the Peninsula, holiday rental in Oak Orchard

24220 Canoe - New end unit townhome in the Peninsula

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Bethany Beach Resort Condo w/ Golf + Tennis, holiday rental in Oak Orchard

Bethany Beach Resort Condo w/ Golf + Tennis

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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33291 Marina Bay - NEW PENINSULA TOWNHOUSE!, holiday rental in Oak Orchard

33291 Marina Bay - NEW PENINSULA TOWNHOUSE!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular Bay Forest Villa near Bethany Beach, holiday rental in Oak Orchard

Spectacular Bay Forest Villa near Bethany Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View Condo by Bethany Beach w/ Balcony!, holiday rental in Oak Orchard

Ocean View Condo by Bethany Beach w/ Balcony!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Premium Bay Forest End Unit, Beautiful, Spacious, Clean, Minutes To Beach, holiday rental in Oak Orchard

Premium Bay Forest End Unit, Beautiful, Spacious, Clean, Minutes To Beach

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Resort Style Home in Ocean View near Bethany Beach, holiday rental in Oak Orchard

Resort Style Home in Ocean View near Bethany Beach

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ocean View Condo w/ Pool & Golf Course Access, holiday rental in Oak Orchard

Ocean View Condo w/ Pool & Golf Course Access

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious townhouse near the bay and close to Rehoboth, Lewes and Bethany, holiday rental in Oak Orchard

Spacious townhouse near the bay and close to Rehoboth, Lewes and Bethany

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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First Floor Contemporary Updates with Top Bay View, Pools, Tennis and Free Activ, holiday rental in Oak Orchard

First Floor Contemporary Updates with Top Bay View, Pools, Tennis and Free Activ

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Bay Views, Pool, Tennis, Kayaks, Ground Floor 2BR 2BA Condo  With Ma, holiday rental in Oak Orchard

Spectacular Bay Views, Pool, Tennis, Kayaks, Ground Floor 2BR 2BA Condo With Ma

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Rental! Water views, free pool, tennis and many other activities. 15 minutes, holiday rental in Oak Orchard

New Rental! Water views, free pool, tennis and many other activities. 15 minutes

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Golf, Kayak, Bike, Fish, Swim, Boat, Hike, and Use of Free Activities in Afforda, holiday rental in Oak Orchard

Golf, Kayak, Bike, Fish, Swim, Boat, Hike, and Use of Free Activities in Afforda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Chic Ocean View Home ~ 5 Mi to Bethany Beach!, holiday rental in Oak Orchard

NEW! Chic Ocean View Home ~ 5 Mi to Bethany Beach!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Chic Townhome w/ Pool Access: 4 Mi to Beach!, holiday rental in Oak Orchard

NEW! Chic Townhome w/ Pool Access: 4 Mi to Beach!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Modern Bishops Landing Home w/ Community Pool, holiday rental in Oak Orchard

NEW! Modern Bishops Landing Home w/ Community Pool

1 bedroom
3 bathrooms
Sleeps 8
Match: Sleeps
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