We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

South Orleans Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $331 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to South Orleans are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 18 Rentals in South Orleans
    Sort by:
    Default
    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Expansive Home by Orleans Town Landing1 / 36
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and comfortable 2-story home sits on a wooded lot within a short distance to a boat ramp and just minutes away from Nauset, Skaket and Pleasant Bay beaches. With four bedrooms and 2.5 baths, it sleeps up to 8 comfortably. The first level features a living room, family room, fully...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this cozy 3 bedroom Cape Cod Cottage in Nauset Village cottage colony! Each bedroom has a full sized bed and the living room provides TV, a DVD player, and plenty of seating for the whole family! The fantastic deck area leads right to the enclosed outdoor shower, great for rinsing off after a...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    East Egg Associaton Property ID: 52204 Property Name: 2 Ellerslie Road 2017 Season! East Egg community. Private access to association beach on Pleasant Bay which is less than half mile away (access from Ellersie to Carlton to Little Bay Rd. sorry but no parking.) Nice open floor plan Central A/C,...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    52 Forest Way 184231 / 18
    (2)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2017 Season! Contemporary home with lots of space, nestled in a quiet wooded area of Orleans. This home is ideal for a casual vacation. 5 Bedrooms (2 Queens, 1 Double, 4 Twins) and 3 Baths. No Pets Accepted. Weekly Rental (7 Night Minimum in Season) _Rent:...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautiful South Orleans home with its own private beach. The interior of the home boasts an open floor plan including a kitchen with granite countertops and center island, spacious dining area, livingroom and a first floor Master Suite with a queen and twin sized bed as well as a private...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisite Custom Built 5BR Home in Orleans, Tons of Stuff for the Kids! (linens included) Peak Summer Weekly Rates: $6,800 Rents Saturday to Saturday If you're looking for upscale accommodations yet plenty for the kids to do, this stunning new home is the one for you. Situated on a quiet...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond (Linens Included) Peak Summer Weekly Rates: $2,950 - $3,800 Rents Saturday - Saturday during peak season If you love nature, privacy and water views this comfortable home is for you. You will wake up each morning to find the...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Save time - get the best South Orleans rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This very special 3 bedroom, 2 bath home overlooks the Namequoit River and features lovely waterviews, two waterside decks, newly remodeled kitchen and great amenities. The property is very close to Pah Wah Conservation area with hiking trails and a sandy Pleasant Bay beach. Launch your kayak from...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2018 Season! Enjoy a Cape Cod vacation. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to the outdoor shower. There are two Bedrooms and a full bathroom on each floor. All 4...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Vacation Home Near Pleasant Bay in East Harwich! This comfortable and conveniently located home is close to Orleans, Chatham and beaches on Pleasant Bay. Enjoy a morning cup of coffee on the bright and sunny enclosed porch or the private back patio. The first floor master bedroom opens out...
    View all property information
    Location Information
    South Orleans, Cape Cod 02645
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Six feet of plush lawn separate the MainHouse from the waters of Pleasant Bay. The large garden has plenty of quiet places for reading, relaxing and/or snoozing in the shade or in the sun. Swim or fish from the dock or the nearby beach. Arrangements for a boat mooring are possible. Off-street...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    #703 Mooncusser: Estate like home! Waterfront! Chef's Kitchen & outdoor fireplace over watertop deck! Nestled on a private lot overlooking Pleasant Bay you will love our Estate Like home adjacent to Wequassett Resort and Golf Club. This architecturally designed home has views of the water from...
    View all property information
    Location Information
    South Orleans, Cape Cod 02645
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home sits on a bluff overlooking Pleasant Bay with panoramic views from almost every room. With 4 bedrooms and 3 baths, it sleeps 8 comfortably. The property offers one level living with all four bedrooms on the main level. Off the back of the home is a deck area as well as a large yard...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ESCAPE from it all to this stunning contemporary, located in South Orleans on a 2 acre lot surrounded by conservation land, one house away from Pleasant Bay. A two minute walk, along one of two scenic paths, leads one to a private association beach on Pleasant Bay. The updated house is remodeled...
    View all property information
    Location Information
    South Orleans, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming remodeled antique home is only 2/10ths of a mile to a Pleasant Bay beach and a short distance to the five star rated Wequassett Resort. The interior has a brand new kitchen with granite counter tops, stainless steel appliances, wide pine floors and opens up to a dining area. There are...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    South Orleans Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    33° 20°
    January
    34° 21°
    February
    38° 26°
    March
    47° 34°
    April

    Additional South Orleans Info

    Go to map view
    • Local time: 11:12 AM (EST)
    List your property
    Owner log in