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.

Longboat Key House 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
    Location
    Any Distance
    from
    Price
    per night
    C$276 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    Suitability
    More filters
    Travellers to Longboat Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    16 Matching Rentals in Longboat KeyView all 128 rentals
    Sort by:
    Default
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean1 / 14
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2015
    We rented both the Luxury Log Cabin and the Tree House next door. Only complaints were in the Log Cabin - they need to put up drape/curtain in loft bedroom for those guests as...
    Reviewed June 30, 2015
    Cons:1. In the picture of the kitchen, it shows a crock pot and salt/pepper shakers. Neither were provided, so don’t plan on a crock pot meal like I did! And bring your own...
    See all reviews
    About this property
    Orchard is a Private Cottage. The garage is shared area, washer and dryer, beach chairs and 3 bikes for you to use. You have outside fire pit and lounge chairs. Housekeeping is off-site. Lawn service arrives in the am on Friday's The very quiet area in the North Village of Longboat Key, Fla. Enjoy...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Multi-level 4 bed/3 bath home w/elevator just a short walk to the beach NOW AVAILABLE DUE TO CANCELLATION! If you are looking for a spacious home that provides a sense of being in an exclusive gated community, is very quiet and tranquil and has access to one of the most beautiful beaches in...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find your tropical oasis in sought after LONGBOAT KEY. Wake to sunrises over your dock overlooking Sarasota Bay and catch the sunset sinking into the Gulf of Mexico-. Enjoy Serenity in this lovely home, or By Bike or Car Minutes to St. Armands' Circle or jump into your Boat; down the Deep Water...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Peaceful Cottage - Houses for Rent in Longboat Key, Florida, United States1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 23, 2018
    Thank you for everything, we enjoyed your cottage. We plan to do this again next holiday. Perfect location, plenty of room for everyone. Nice to have beach chairs, and bikes...
    See all reviews
    About this property
    Fully equipped cottage reflecting its own unique style of a beach getaway in paradise, full of character, and quaint as can be! Very clean, and well maintained. This cottage is on a private lot with a separate entrance and parking. Laundry room with washer and dryer in garage. The residence has...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Longboat Key Retreat1 / 8
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 9, 2016
    Located on it's own in very quiet area we did not feel safe as no other people about. House was not as clean as it should have been lots of bugs etc. well equipped, not as near...
    See all reviews
    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    637 Norton1 / 70
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 2, 2018
    We loved our month in longboat key. The house was perfect. Large, sunny, and very comfortable. Four large bedrooms with king size beds that were so comfortable. The kitchen was...
    See all reviews
    About this property
    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 block Live the Florida lifestyle in this beautiful, comfortable 4 bedroom, 3 bath private home located in the Sleepy Lagoon on the quaint end of Longboat key. This home...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 2400 sqft 3 bedroom Spanish style house with a beautiful huge fully Italian tiled sunken living room. The house has large glass windows making it bright and well lit. The panoramic view of the canal is visible from all the areas including the 2 bedrooms. living room and dining room. You...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Longboat Key rentals sent straight to your email!
    Get the List
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your tropical island oasis awaits! Welcome to this modern, updated 2-bedroom townhouse with added community benefits on Long Boat Key. This beauty is located in the popular Cedars East Tennis Resort. Amenities include a heated pool, fishing pier, tennis courts, and fitness center. Long Boat Key is...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Washer
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designer's hidden home: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & TV Our Venetian Villa is nestled on the placid Longboat Key. With a short drive from the airport, Ringling Museum, St....
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly built waterfront home will take you to another place and time. Tucked away in native tropical vegetation perched on the Bays edge looking out to Longboat Pass, this home is the perfect retreat for a couple or small group. Modern, open floorpan with a Scandinavian feel boasts hardwood...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    6 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for tropical seclusion on a private island? Gorgeous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private Island Polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 18
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tennis resort boasts gorgeous views of Mangrove wetland and is just a short walk from stunning gulf beaches! The community pool makes this a lovely family-friendly getaway. Find great bird-watching and wildlife viewing from the balcony, or stroll through Mangrove tunnels on the boardwalk....
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in