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.

Holiday Rentals and Homes in Portsmouth, VA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    €0
    €143 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Portsmouth area holiday rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    Portsmouth
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Owner online now
    Show Prices
    Payment Protection

    The following rentals are within 25 kilometers of Portsmouth, Virginia.

    Norfolk
    1 Bedroom, Sleeps 2 | Quick View
    Owner online now
    Show Prices
    Payment Protection
    1 / 19
    5 of 5 stars (12) Excellent
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Come get away for a few days and enjoy the beach! This is a cozy studio above our detached garage on our 1/2 acre lot, separate from our main home for your privacy. It has a nice beach house feel to it that our guests always compliment! We have everything you need including a handful of snacks,... View all property information
    Location Information
    Norfolk, Virginia 23503
    1 / 27
    5 of 5 stars (2) Excellent
    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Patio
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    AN IDYLLIC locale for family excursions, weddings & receptions and/or a relaxing respite from the rat race! Imagine an expansive retreat reminiscent of Frank Sinatra, Dean Martin & Sammy Davis Jr.! Wiseacre Estate is a whimsical 4000sf Frank Lloyd Wright-inspired property built in 1962. Enjoy... View all property information
    Location Information
    Norfolk, Virginia 23518
    5 of 5 stars Reviewed 14 May 2015
    Wiseacre Estate was beautiful, spacious, had amazing views (great sunrises and sunsets), and had all of the amenities needed (kitchen, laundry, living, bathroom, etc.). Our host...
    5 of 5 stars Reviewed 13 April 2015
    Me and my husband had an outstanding time staying at chucks house. It was a little to our shock that he was going to be there with us, but he was the best host ever. We found not...
    See all reviews
    Norfolk
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Owner online now
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Patio
    • Waterfront
    • Porch
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Elegance, contemporary style, perfectly hand wrapped in seclusion. A luxurious masterpiece designed for those who live life on top. Delicately placed on the peaceful shores of the Chesapeake Bay, just a wind's whisper from Va Beach and the Atlantic Ocean. Perfect for couples retreats, buddy trips,... View all property information
    Location Information
    Norfolk, Virginia 23503
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Parking
    • Satellite TV
    • Wi-Fi
    • Porch
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful Brick home located in Chesapeake....minutes from downtown Norfolk and Virginia Beach. Great for a family vacation or for business travel. We have a large 4 bedroom home with 2.5 bath. Large living room, formal dining room and den...also an eat in kitchen. Washer and Dryer available... View all property information
    Location Information
    Chesapeake, Virginia 23322
    1 / 22
    5 of 5 stars (1) Excellent
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Balcony
    • Housekeeping...
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Imagine an expansive retreat reminiscent of Frank Sinatra, Dean Martin & Sammy Davis Jr.! Wiseacre Estate is a whimsical 4000sf Frank Lloyd Wright-inspired property built in 1962. Enjoy the tranquility of this authentic Mid-Century Modern home... with a cavernous 650sf great room (20-foot... View all property information
    Location Information
    Norfolk, Virginia 23518
    5 of 5 stars Reviewed 5 August 2015
    My extended family recently (July 26-Aug 2) converged on the Norfolk area for vacation. We rented this home, and it was the best decision we could have made for accommodations. It...
    See all reviews
    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Newly Remodeled two bedroom home in Colonial Place....historic neighborhood in Norfolk. Close to Old Dominion University and Norfolk Naval Base. Walking distance to local restaurants, coffee shops etc. Beautifully decorated with hardwood floors and all new furniture. We are excited to host... View all property information
    Location Information
    Norfolk, Virginia 23508
    Norfolk
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
    Owner online now
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Waterfront home, close to Williamsburg, the historic triangle, or Virginia Beach. There is a beach on site as well as a 2nd beach that is 7 miles long, AND not crowded. 4 bedroom with lots of parking, (no events sorry). Home has large waterfront deck. Large dining table, fireplace for winter.... View all property information
    Location Information
    Norfolk, Virginia 23503
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 31
    5 of 5 stars (17) Excellent
    Hampton
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Washer
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    You'll love watching the breathtaking sunrise over the Chesapeake Bay from your Spacious Private Porch in this One-of-a-Kind Grandview Island pet-friendly apartment. With Panoramic Views from the Living Room, Kitchen and Dining area you can enjoy the view from inside as well as outside. Relax at... View all property information
    Location Information
    Hampton, Virginia 23664 1916
    5 of 5 stars Reviewed 29 October 2015
    A great place to get away from the craziness of our life. Nice apartment, great mattress on the bed, nicely supplied kitchen, and a great owner. My husband greatly enjoyed the...
    5 of 5 stars Reviewed 5 August 2015
    We've been renting vacation houses up and down the East Coast for over 20 years and this is one of the best, if not THE best. This was one of those rare occasions where our...
    See all reviews
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Washer
    • Porch
    • Grill
    • DVD Player
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a great family home located in beautiful Chesapeake Virginia. We are 20 minutes to downtown Norfolk and 20 minutes to Virginia Beach. This is a perfect space for multi-families to come together. We offer 4 bedrooms and 2 1/2 bath in the main home then a separate bedroom and bath (the... View all property information
    Location Information
    Chesapeake, Virginia 23322
    1 / 29
    5 of 5 stars (24) Excellent
    Chesapeake
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Owner online now
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Housekeeping...
    • Patio
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chesapeake Bay beachfront rental facing due east with five bedrooms, two full baths plus outside private shower. Just steps to the private beach and fantastic sunrises. Fully equpipped kitchen, wetbar, breakfast bar, two coffee makers, 7 TV's with cable, free wireless internet, W/D, gas FP,... View all property information
    Location Information
    Chesapeake, Virginia 23066
    4 of 5 stars Reviewed 27 May 2015
    We stayed at the Sandbar in mid May for our son's wedding on Gwynn's Island Family, friends and groomsman all stayed at the Sandbar throughout the weekend. The kitchen island...
    5 of 5 stars Reviewed 21 October 2014
    Clean well stock home. Everything needed in a home away from Home.The view of sunset is amazing shining over the bay. The best family vacation ever
    See all reviews
    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Grill
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come enjoy our beautiful five bedroom home within steps to the Chesapeake Bay. Huge master bedroom and expansive views of the bay. Opening living space, with three large out door decks. Fish, Hunt for Shells, or just walk along the 7 miles of quiet, locals-mostly beach. Minutes from the Atlantic... View all property information
    Location Information
    Norfolk, Virginia 23518