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Oak Orchard Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
30 rentals in Oak Orchard.
Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community, holiday rental in Oak Orchard
Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community, holiday rental in Oak Orchard
Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community, holiday rental in Oak Orchard

Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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27531 S Nicklaus Ave - Four bedroom home in the amenity filled Peninsula!, holiday rental in Oak Orchard
27531 S Nicklaus Ave - Four bedroom home in the amenity filled Peninsula!, holiday rental in Oak Orchard
27531 S Nicklaus Ave - Four bedroom home in the amenity filled Peninsula!, holiday rental in Oak Orchard

27531 S Nicklaus Ave - Four bedroom home in the amenity filled Peninsula!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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!, holiday rental in Oak Orchard
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!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Peninsula  0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach., holiday rental in Oak Orchard
The Peninsula  0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach., holiday rental in Oak Orchard
The Peninsula  0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach., holiday rental in Oak Orchard

The Peninsula 0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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), holiday rental in Oak Orchard
The Peninsula- 5 Star Resort-Townhome (Near Rehoboth), holiday rental in Oak Orchard

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

Holiday Rental House
4 bedrooms
4 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, holiday rental in Oak Orchard
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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So close to all the action!, holiday rental in Oak Orchard
So close to all the action!, holiday rental in Oak Orchard
So close to all the action!, holiday rental in Oak Orchard

So close to all the action!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet community with access to a ramp to kayak, paddle board, holiday rental in Oak Orchard
Quiet community with access to a ramp to kayak, paddle board, holiday rental in Oak Orchard
Quiet community with access to a ramp to kayak, paddle board, holiday rental in Oak Orchard

Quiet community with access to a ramp to kayak, paddle board

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Peninsula getaway with pools, hot tubs, sports courts, & on-site golf, holiday rental in Oak Orchard
Stunning Peninsula getaway with pools, hot tubs, sports courts, & on-site golf, holiday rental in Oak Orchard
Stunning Peninsula getaway with pools, hot tubs, sports courts, & on-site golf, holiday rental in Oak Orchard

Stunning Peninsula getaway with pools, hot tubs, sports courts, & on-site golf

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Fabulous Rental - In the Peninsula an Exclusive Gated Private Community, holiday rental in Oak Orchard
Fabulous Rental - In the Peninsula an Exclusive Gated Private Community, holiday rental in Oak Orchard
Fabulous Rental - In the Peninsula an Exclusive Gated Private Community, holiday rental in Oak Orchard

Fabulous Rental - In the Peninsula an Exclusive Gated Private Community

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3 Bedroom, 2.5 bath condo with garage on the 6th green!, holiday rental in Oak Orchard
3 Bedroom, 2.5 bath condo with garage on the 6th green!, holiday rental in Oak Orchard
3 Bedroom, 2.5 bath condo with garage on the 6th green!, holiday rental in Oak Orchard

3 Bedroom, 2.5 bath condo with garage on the 6th green!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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6 Bedroom Family Retreat in The Peninsula, holiday rental in Oak Orchard
6 Bedroom Family Retreat in The Peninsula, holiday rental in Oak Orchard
6 Bedroom Family Retreat in The Peninsula, holiday rental in Oak Orchard

6 Bedroom Family Retreat in The Peninsula

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Because this summer should be unforgettable., holiday rental in Oak Orchard
Because this summer should be unforgettable., holiday rental in Oak Orchard
Because this summer should be unforgettable., holiday rental in Oak Orchard

Because this summer should be unforgettable.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Amenity filled rental with an amazing view within the five star Peninsula resort, holiday rental in Oak Orchard
Amenity filled rental with an amazing view within the five star Peninsula resort, holiday rental in Oak Orchard
Amenity filled rental with an amazing view within the five star Peninsula resort, holiday rental in Oak Orchard

Amenity filled rental with an amazing view within the five star Peninsula resort

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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1st floor suite, car charger, 6 patios and porches at 5 star Peninsula resort!, holiday rental in Oak Orchard
1st floor suite, car charger, 6 patios and porches at 5 star Peninsula resort!, holiday rental in Oak Orchard
1st floor suite, car charger, 6 patios and porches at 5 star Peninsula resort!, holiday rental in Oak Orchard

1st floor suite, car charger, 6 patios and porches at 5 star Peninsula resort!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful home situated on the 2nd hole of the golf course., holiday rental in Oak Orchard
Beautiful home situated on the 2nd hole of the golf course., holiday rental in Oak Orchard
Beautiful home situated on the 2nd hole of the golf course., holiday rental in Oak Orchard

Beautiful home situated on the 2nd hole of the golf course.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful & Relaxing Vacation Home with all amenities, holiday rental in Oak Orchard
Beautiful & Relaxing Vacation Home with all amenities, holiday rental in Oak Orchard
Beautiful & Relaxing Vacation Home with all amenities, holiday rental in Oak Orchard

Beautiful & Relaxing Vacation Home with all amenities

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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33585 Windswept Unit 7201 - Near all of the Peninsula amenities, holiday rental in Oak Orchard
33585 Windswept Unit 7201 - Near all of the Peninsula amenities, holiday rental in Oak Orchard
33585 Windswept Unit 7201 - Near all of the Peninsula amenities, holiday rental in Oak Orchard

33585 Windswept Unit 7201 - Near all of the Peninsula amenities

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Three bedroom condominium in the Windswept community at The Peninsula!, holiday rental in Oak Orchard
Three bedroom condominium in the Windswept community at The Peninsula!, holiday rental in Oak Orchard
Three bedroom condominium in the Windswept community at The Peninsula!, holiday rental in Oak Orchard

Three bedroom condominium in the Windswept community at The Peninsula!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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33033 Conservation - New Peninsula Home with four bedrooms!, holiday rental in Oak Orchard
33033 Conservation - New Peninsula Home with four bedrooms!, holiday rental in Oak Orchard
33033 Conservation - New Peninsula Home with four bedrooms!, holiday rental in Oak Orchard

33033 Conservation - New Peninsula Home with four bedrooms!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Single Family home in The Peninsula, holiday rental in Oak Orchard
Single Family home in The Peninsula, holiday rental in Oak Orchard
Single Family home in The Peninsula, holiday rental in Oak Orchard

Single Family home in The Peninsula

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Comfy 3-Bedroom Near The Beach With A Pool & Grill, holiday rental in Oak Orchard
Comfy 3-Bedroom Near The Beach With A Pool & Grill, holiday rental in Oak Orchard
Comfy 3-Bedroom Near The Beach With A Pool & Grill, holiday rental in Oak Orchard

Comfy 3-Bedroom Near The Beach With A Pool & Grill

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Peninsula retreat with pools, hot tubs, sports courts, & ample golfing, holiday rental in Oak Orchard
Amazing Peninsula retreat with pools, hot tubs, sports courts, & ample golfing, holiday rental in Oak Orchard
Amazing Peninsula retreat with pools, hot tubs, sports courts, & ample golfing, holiday rental in Oak Orchard

Amazing Peninsula retreat with pools, hot tubs, sports courts, & ample golfing

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Peninsula townhome w/ indoor/outdoor pools, on-site golf, holiday rental in Oak Orchard
The Peninsula townhome w/ indoor/outdoor pools, on-site golf, holiday rental in Oak Orchard
The Peninsula townhome w/ indoor/outdoor pools, on-site golf, holiday rental in Oak Orchard

The Peninsula townhome w/ indoor/outdoor pools, on-site golf

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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33436 Marina Bay - New four bedroom home in the Peninsula!, holiday rental in Oak Orchard
33436 Marina Bay - New four bedroom home in the Peninsula!, holiday rental in Oak Orchard
33436 Marina Bay - New four bedroom home in the Peninsula!, holiday rental in Oak Orchard

33436 Marina Bay - New four bedroom home in the Peninsula!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Windswept Dr  Condo in a quiet, golf course community close to Rehoboth Beach, holiday rental in Oak Orchard
Windswept Dr  Condo in a quiet, golf course community close to Rehoboth Beach, holiday rental in Oak Orchard
Windswept Dr  Condo in a quiet, golf course community close to Rehoboth Beach, holiday rental in Oak Orchard

Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Millsboro Cottage w/ Deck & Indian River Bay Views, holiday rental in Oak Orchard
Millsboro Cottage w/ Deck & Indian River Bay Views, holiday rental in Oak Orchard
Millsboro Cottage w/ Deck & Indian River Bay Views, holiday rental in Oak Orchard

Millsboro Cottage w/ Deck & Indian River Bay Views

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Luxury 6BR, 6.5 Baths, 5000 sqft * The Peninsula, Linen & EV charger provided, holiday rental in Oak Orchard
Luxury 6BR, 6.5 Baths, 5000 sqft * The Peninsula, Linen & EV charger provided, holiday rental in Oak Orchard
Luxury 6BR, 6.5 Baths, 5000 sqft * The Peninsula, Linen & EV charger provided, holiday rental in Oak Orchard

Luxury 6BR, 6.5 Baths, 5000 sqft * The Peninsula, Linen & EV charger provided

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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RANCH WITH CACTUSES   weekly and monthly rentals up to 35% OFF, holiday rental in Oak Orchard
RANCH WITH CACTUSES   weekly and monthly rentals up to 35% OFF, holiday rental in Oak Orchard
RANCH WITH CACTUSES   weekly and monthly rentals up to 35% OFF, holiday rental in Oak Orchard

RANCH WITH CACTUSES weekly and monthly rentals up to 35% OFF

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing!  Osocozy.  Waterfront home on the Indian River Bay.  Lovely views!, holiday rental in Oak Orchard
New Listing!  Osocozy.  Waterfront home on the Indian River Bay.  Lovely views!, holiday rental in Oak Orchard
New Listing!  Osocozy.  Waterfront home on the Indian River Bay.  Lovely views!, holiday rental in Oak Orchard

New Listing! Osocozy. Waterfront home on the Indian River Bay. Lovely views!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Showing results 1-30 of 30
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