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Orleans Rentals

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From $568 per night (USD)
VRBO
Walk to Nauset Beach, Updated and Cozy!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 15581 - Beach Daze: Walk to Nauset Beach, Updated and Cozy! The Space: Discover your dream Cape Cod vacation i ...
From $568 per night (USD)
VRBO
From $814 per night (USD)
VRBO
NEW! Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $814 per night (USD)
VRBO
From $684 per night (USD)
VRBO
Near Wequassett Resort and Golf Club in Harwich, overlooking a cranberry bog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this spacious and inviting Harwich rental, perfectly situated near the Wequassett Resort and Golf Club, with b ...
From $684 per night (USD)
VRBO
From $265 per night (USD)
VRBO
Beautiful Historic Home Within a Mile of Crystal Lake
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
***NEW TO THE MARKET*** This amazing, refurbished Post and Beam Antique home is known as the Gould-Linnell House which ...
From $265 per night (USD)
VRBO
From $263 per night (USD)
VRBO
Charming 1BR, Pet Friendly, Minutes to Beaches, Golf, Dining, Shopping(2396)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to this charming and cozy short-term rental apartment, nestled in a peaceful neighborhood on a quiet dead-end st ...
From $263 per night (USD)
VRBO
From $2719 per night (USD)
Expedia
Beautiful sunsets and saltwater views from every room
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Magnificent, wraparound saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to ...
From $2719 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Contemporary with an eye out for comfort and space, close to bike path,conservation, beach, village.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Contemporary 3BR, 2BA home designed for comfort and space with an airy, open layout and cozy retreat areas like a loft w ...
From $302 per night (USD)
VRBO
From $507 per night (USD)
Expedia
Nauset Harbor Cottage: 112-O Charming Coastal Retreat with Breathtaking Views – East Orleans
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties. Charming Coastal Retreat with Breathtaking Views – ...
From $507 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Charming 4-bedroom house with AC and WiFi steps from Wequassett Resort
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to your perfect Cape Cod summer with this stunning rental property located steps away from the beauty of Pleasant ...
From $808 per night (USD)
VRBO
From $643 per night (USD)
Expedia
3 Cottages, Walk to Nauset Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 15585 - Beach Charmer: 3 Cottages, Walk to Nauset Beach! The Space: Escape to Orleans, where this charming, do ...
From $643 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Great location with Water Views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: 17710 - Captains Cottage: Great location with Water Views! The Space: Escape to the charm of Harwich, where th ...
From $425 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Studio, Walk to Nauset Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: 15587 - Sea Rose: Studio, Walk to Nauset Beach! The Space: Experience a true Cape Cod cottage at this charming ...
From $145 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Studio perfect for 3, Walk to Nauset Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: 15588 - Sea Wind: Studio perfect for 3, Walk to Nauset Beach! The Space: Experience a true Cape Cod cottage at ...
From $152 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Cozy Cottage Walk to Nauset Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: 15586 - Quarterdeck: Cozy Cottage, Walk to Nauset Beach! The Space: Just a 0.2 miles walk to Nauset Beach, thi ...
From $356 per night (USD)
Expedia
From $639 per night (USD)
VRBO
2025 Foremast: Charming Cottage w/ Panoramic Town Cove Views, Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony of Anchor ...
From $639 per night (USD)
VRBO
From $666 per night (USD)
VRBO
2025 Bell Buoy: Adorable Cottage w/ Sparkling Town Cove Views, Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Description Enjoy use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony ...
From $666 per night (USD)
VRBO
From $647 per night (USD)
VRBO
2025 Topsail: Delightful Waterfront Cottage on Town Cove, Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony of Anchor ...
From $647 per night (USD)
VRBO
From $564 per night (USD)
VRBO
2025 Pilot House: Waterfront Cottage w/ Deck on Town Cove, Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony of Anchor ...
From $564 per night (USD)
VRBO
From $523 per night (USD)
VRBO
2025 Top Deck: Lovely Condo w/ Deck Overlooking Town Cove, Pet Friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy the use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony of Anchor ...
From $523 per night (USD)
VRBO
From $565 per night (USD)
VRBO
2025 Mate's Quarters: 2-Bed Condo w/ Water Views of Town Cove, Pet Friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the use of the shared private dock for kayaking or fishing. Located in the lovely seaside cottage colony of Anchor ...
From $565 per night (USD)
VRBO
From $582 per night (USD)
VRBO
South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
This home is professionally managed by Pretty Picky Properties Waterfront, Six Bedrooms, Free Boating Bonus! NEW Listi ...
From $582 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This home is professionally managed by Pretty Picky Properties Spectacular Pleasant Bay Views, Free Boating Bonus! NEW ...
From $569 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Walk to Beach, Close to Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 15583 - Tonset Cottage: Walk to Beach, Close to Town! The Space: Escape to this charming Orleans home, perfect ...
From $302 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Coastal Comfort Near Orleans Adventures
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 15584 - Harvey's Hideaway: Coastal Comfort Near Orleans Adventures The Space: Discover the perfect Cape Cod re ...
From $373 per night (USD)
Expedia
From $844 per night (USD)
VRBO
BEAUTIFUL WATERFRONT HOME, WALK TO TOWN - In Charming Orleans!
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Welcome to your perfectly curated Cape escape, Crimson on the Cove! Everything Orleans has to offer is at your fingert ...
From $844 per night (USD)
VRBO
Click For Pricing
Expedia
Nauset Winds - Classic Cape Cod Getaway - Easy Walk to Nauset Beach in Orleans
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Nauset Winds, a charming Cape Cod beachhouse tucked away on a sleepy dirt road in the highly sought after nei ...
Click For Pricing
Expedia
From $1904 per night (USD)
VRBO
Private Beach 6 Bedroom Newly Renovated!
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
One of a kind, 6-bedroom estate situated on a small neighborhood beach on Little Pleasant Bay. The Home sits on 4 acres ...
From $1904 per night (USD)
VRBO
Click For Pricing
Expedia
Lavender Hollow - Breathtaking Marshfront Retreat Near Boat Meadow Beach-Eastham
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Lavender Hollow, a serene retreat tucked along the marshlands of Eastham. This beautifully renovated Cape Cod ...
Click For Pricing
Expedia
From $478 per night (USD)
VRBO
Close to Beaches: Gem w/ Yard & Sunroom in Orleans
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Families Welcome | Multiple Living Spaces | 2 Mi to Nauset Beach Embark on your dream East Coast getaway and stay at th ...
From $478 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Orleans Beach Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Spacious 2 bedroom home close to Nauset Beach! Central ac. Nice sized kitchen with eat in area. Living room off kitchen ...
From $406 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Salt River Retreat - Easy Walk to Scenic Kent's Point - Pet Friendly!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Salt River Retreat, a delightful family home tucked away in a coveted Orleans neighborhood. This charming get ...
From $535 per night (USD)
VRBO
Click For Pricing
Expedia
Peaceful and private vacation rental on the pond!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Peaceful and private vacation rental on the pond! This charming 3 bedroom (king, queen, full), 3 bathroom home in Orlean ...
Click For Pricing
Expedia
From $635 per night (USD)
VRBO
Harbor Vista: 003-O Sleek & Modern East Orleans Retreat with Stunning Ocean Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Sleek & Modern East Orleans Retreat with Stunning O ...
From $635 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Child Friendly, Charming 3-Bedroom Cape in Unbeatable Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to "1-Mile House", where everything you could ever need is only 1 mile away! Skaket Beach (best sunsets), Eldrid ...
From $384 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Sunrise Cottage Brewster - 1 Bed Cottage, Perfect for a Cozy Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Cape Cod Property 121, a cozy and inviting retreat nestled in the charming town of Brewster. This delightful ...
From $228 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Pondfront, 1 Mile to Nauset Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 15582 - Calm Waters: Pondfront, 1.4 Miles to Nauset Beach! The Space: Along the serene shores of Uncle Harvey’ ...
From $425 per night (USD)
Expedia
From $2678 per night (USD)
VRBO
ON PLEASANT BAY - TOPSIDE MAIN HOUSE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
<p>Located in Orleans, this 4-bedroom, 3.5-bathroom vacation home lets you experience it all. Fans of nature and the out ...
From $2678 per night (USD)
VRBO
From $1594 per night (USD)
Expedia
Nauset Dream: 024-O Luxury 5 Bedroom East Orleans Home with Heated Pool, Spa
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This property is professionally managed by Pretty Picky Properties. Luxury 5 Bedroom East Orleans Home with Heat ...
From $1594 per night (USD)
Expedia
From $563 per night (USD)
VRBO
This charming Brewster retreat offers the perfect blend of coastal elegance and modern comfort.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming Brewster retreat offers the perfect blend of coastal elegance and modern comfort. New Deck Built and Outd ...
From $563 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Relax Close to Chatham & Orleans (2401)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in a quiet neighborhood just off Route 28, this inviting Harwich home is perfectly situated for your Cape Cod es ...
From $614 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Charming home steps to beach, includes 2 full units with patio, grill, & views
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Nauset Beach Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $521 per night (USD)
VRBO
From $587 per night (USD)
Expedia
Waterfront Retreat in South Orleans, New to Rental Market! (2402)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in the quiet community of South Orleans, this stunning upside-down home offers a serene escape with direct water ...
From $587 per night (USD)
Expedia
From $327 per night (USD)
VRBO
4 Bedroom Meetinghouse Pond Waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
9
Scenic waterfront property with tranquil water views and saltwater access all the way to Chatham. This delightful home w ...
From $327 per night (USD)
VRBO
From $1078 per night (USD)
VRBO
Private Waterfront Property with Water Access to Nauset Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Wonderful Family Waterfront Retreat with Scenic Water Views of Woods Cove, and Nauset Beach in Orleans to the Coast Guar ...
From $1078 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Pet Friendly Home in East Orleans
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Pet Friendly property only 1.6 miles to Nauset Beach and close to Orleans Center and East Orleans Village. This charmi ...
From $293 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Private Home With Marsh Views 1 Mile From Boat Meadow Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful Cape style home with lots of updates and sits overlooking conservation marsh views. The first floor of this ...
From $648 per night (USD)
VRBO
From $763 per night (USD)
VRBO
Beautifully Renovated Home Near Pleasant Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home has been painstakingly renovated with love and thoughtful improvements for tenants to create unforgettable mem ...
From $763 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Skaket Beach Area Home with Association Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Home Near Skaket Beach with Association Beach Access Be near one of Orleans most popular vacation areas: Skaket Beach! ...
From $522 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Steps To Skaket Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Views of and Steps to Skaket Beach! This adorable one-story beach cottage has delighted vacationers for many years. En ...
From $613 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Charming 3-bedroom house with WiFi, Dogs considered, in Orleans
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Traditional Cape House, the Best of Cape Cod, and the Get-Away you need to unwind in Orleans at this tranquil house with ...
From $456 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Cozy Cape Cod Escape – Perfect for Families, Quiet & Convenient Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to your perfect Cape Cod escape! This classic 3-bedroom Cape-style home is tucked away in a quiet neighborhood, ...
From $478 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Central location! Bungalow for 2 + Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Cape Cod from our single-level house in Orleans. Tucked away in a quiet area yet incredibly central, this ideal ...
From $272 per night (USD)
Expedia
From $1181 per night (USD)
VRBO
Luxurious 5-Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water!: 013-OP
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This property is professionally managed by Pretty Picky Properties Luxurious 4-Bedroom Retreat with Heated Pool & Hot ...
From $1181 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Nauset Vista: 006-OO East Orleans Contemporary—Easy Access to Nauset Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home is professionally managed by Pretty Picky Properties. Nauset Vista: East Orleans Contemporary—Easy Access to ...
From $488 per night (USD)
Expedia
From $1152 per night (USD)
VRBO
Saltwater Serenity - Oceanview Retreat with Pool and Expansive Outdoor Living
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Welcome to this stunning Cape Cod retreat perched in a quiet Orleans neighborhood with panoramic views of the Atlantic O ...
From $1152 per night (USD)
VRBO
From $246 per night (USD)
VRBO
The Cherry, cozy, charming and romantic.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Eastham at this adorable apartment. This cozy space features a large open living area with a sunny full kitche ...
From $246 per night (USD)
VRBO
From $640 per night (USD)
VRBO
Lovely House 5 Min to Beach with Deck, Grill, Garage
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Just 5 minutes from Cape Cod's stunning beaches like Rock Harbor and near Orleans' many shops & restaurants. This spacio ...
From $640 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Skaket Creek Landing - Renovated Orleans Retreat 3 Minutes from Skaket Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Skaket Creek Landing! This meticulously restored vacation home is nestled in the heart of the well-regarded N ...
From $436 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Cheerful Home Close to Bay and Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This bright and cheerful home approximately one half mile from either the bay or the center of Orleans. So close to Roc ...
From $511 per night (USD)
VRBO
From $227 per night (USD)
VRBO
Charming 2-bedroom apartment with AC, WiFi in serene Eastham, near Rock Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This Eastham ground floor apartment offers our guests a quiet, serene, secure location surrounded by beautiful gardens, ...
From $227 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Charming 3-bedroom house with AC, WiFi in awesome Brewster w bike trail access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You made it, you're on vacation! You take the drive out to the Cape and pull up to your home away from home. You open th ...
From $423 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Charming 1-bedroom cottage in fabulous Eastham! Close to beaches and bike paths.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make yourself at home in this quaint cottage retreat in Eastham. This 1-bedroom hideaway offers soothing vibes and comes ...
From $250 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Charming 1-bedroom apartment in beautiful Brewster with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to this charming apartment in Brewster. This wonderful rental features a cozy bedroom with a king bed, a lovely ...
From $361 per night (USD)
VRBO
From $422 per night (USD)
VRBO
Family Friendly Cape Escape
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to this comfortable and spacious 4-bedroom, 2-bath beach house located in a quiet, family-friendly neighborhood o ...
From $422 per night (USD)
VRBO
From $555 per night (USD)
VRBO
New! Surf, S'mores + Soak w/ Hot Tub, AC, Firepit, Near Iconic Beaches
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
*New* This Fall, guests at Orleans Holiday House receive a complimentary Deluxe Fireside Gift with any stay booked - fir ...
From $555 per night (USD)
VRBO
From $667 per night (USD)
VRBO
Charming 1800s Cape Cod home near beaches, bike trails, sunset hotspots & more!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Get away from it all with a stay in a well-appointed, historical vacation home on Cape Cod. Situated in the village of ...
From $667 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Rock Harbor! Nestled just steps from the picturesque Rock Harbor in Orleans, our newly renovated Cape Cod ho ...
From $308 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Association Access to Skaket Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Exceptional home close to Skaket Beach in Orleans. This vibrant and tastefully decorated home is located approximately ...
From $596 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Escape to this rare beachfront retreat where the sea is your front yard
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beachfront studio condo features a fully equipped kitchen and everything you need for a relaxing stay. Unlike inla ...
From $513 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Private Pool Near Pleasant Bay Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
NEW LISTING - Cozy Cottage, Air Conditioning, Private Pool, Under 300 Steps to Pleasant Bay Beach Within one of South O ...
From $335 per night (USD)
VRBO
From $621 per night (USD)
VRBO
Classic Cape Beauty in East Orleans, close to Asa's Landing & Weesit Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This classic Cape beauty with center fireplace is located in the desirable Tonset area of Orleans. Enjoy nearby access t ...
From $621 per night (USD)
VRBO
From $1235 per night (USD)
Expedia
Liberty: 030-O Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Brand New Luxury Home in Orleans, Heated Pool, Steps ...
From $1235 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Family Fun: Huge Game Room, Outdoor Shower & Walk 2 Lake – 10 min to Ocean & Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our Orleans retreat—perfect for families and groups looking for fun, relaxation, and convenience. This spacio ...
From $672 per night (USD)
VRBO

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Results: 473 Rentals