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
    $370 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    South Orleans is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    All 22 Rentals in South Orleans
    Sort by:
    Default
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Central Air and All Amenities! Enjoy Brand New Cape Style Vacation Rental Home in Orleans! SPECIAL Get Aug 26-Sept 2  just $2,500!!! The actual Address is 5 White Cedar but for Google Mapping we are using the lot next door: 80 Portanimicut Road Well appointed, brand new construction, 3450 Square...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    $1745-$2495 ($100 less if not bringing pet) Rates include all charges; no hidden fees! As a vacation rental, this exquisite 5 bedroom/3 full bath home in South Orleans hits all the right notes exactly on pitch. It is both elegant and relaxed, with plenty of indoor and outdoor space to comfortably...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Satellite TV
    • Ocean Views
    • Balcony
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 26, 2016
    I stayed here on my honeymoon many years ago, and have returned every year since then. I could roll out of bed, onto the deck, and into the water without walking 5 steps...
    See all reviews
    About this property
    The BoatHouse is unique. Built and furnished in Cape Cod Cottage style, it sits literally right on Pleasant Bay with deck and stairs leading into the water. In the master bedroom look out across Pleasant Bay before you get out of bed. Full bathroom inside and delightful outside shower. Lounge,...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable, updated South Orleans home offers 4 bedrooms and 3 baths with plenty of room to stretch out on your vacation! It features an open layout living/dining area, with a cute sunroom right off the main living space. The first floor boasts an updated, fully equipped kitchen, as well as a...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    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
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fall in Love with this expansive 4-BR. Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah landing, where you can launch your boat, kayaks or canoes, or sail to the Outer Beach. The Pah Wah Point hiking trails and a sandy beach at Little Pleasant Bay...
    View all property information
    Location Information
    South Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor soothing views of Pleasant Bay, Nauset Bar and the Ocean beyond! Gorgeous sun and moon rises too! Swim, fish, shell or relax from private beach and dock - 3 minutes - door to dock. A large, sunny & beautifully maintained home in lovely East Egg affords the space and amenities to insure a...
    View all property information
    Location Information
    South Orleans, Cape Cod 02662
    Rental Home - 5 Bedrooms, 4 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
    • 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
    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
    Rental Home - 4 Bedrooms, 3 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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 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 beautiful 4 bedroom, 3 bath South Orleans home is located in a quiet neighborhood, just a short drive to Pleasant Bay. The first level of the home features a spacious kitchen and dining area, large living area with a/c unit, and a Master Suite with a king sized bed and private bath with shower...
    View all property information
    Location Information
    South Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 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
    This 4 bedroom, 3 bath home sits on Namequoit River in Orleans and offers a private dock off the backyard area. The first level of the home offers one bedroom with a king sized bed and the second level features three additional bedrooms, two with a queen sized bed and one with two twins. The...
    View all property information
    Location Information
    South Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    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
    • 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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • 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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • 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 2017 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, 3 Bathrooms, Sleeps 8
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Patio
    • Washer
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 S. Little Bay Road, South Orleans (ID# 55120) 2017 Season! Lovely home in East Egg Community of South Orleans with views, beach access, central air conditioning and a beautiful expansive yard. Views of Pleasant Bay from almost every room as well as a great brick patio for everyone to enjoy. This...
    View all property information
    Location Information
    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    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
    South Orleans Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    65° 52°
    September
    55° 42°
    October
    45° 34°
    November
    39° 26°
    December

    Additional South Orleans Info

    Go to map view
    • Local time: 12:55 PM (EDT)
    List your property
    Owner log in