Sarasota - We currently have 36 Sarasota vacation homes, condos and villas listed on this page!

Cultural Events Abound in Sarasota, Florida

The city of Sarasota, Florida came became a household word for many Americans in September, 2001 for it was here that President George Bush was visiting a local elementary school when he received word of the 9/11 terrorist attacks. Located in Sarasota County, the city is situated along the Gulf Coast of Florida between Tampa Bay and Fort Myers. The city limits include not just portions of the mainland, but also several of Florida's famous barrier islands, including Siesta Key, Otter Key, and Bird Key.



Sarasota boasts more than 50,000 permanent residents, making it a medium-sized city for its region. There are many Sarasota vacation homes available as short or long-term rentals, in part because this region of Florida is one that was greatly affected by the increase in housing price levels during the first eight years of the new millennium. With the subsequent crash in values, many people who had previously maintained second homes here decided to recoup some of their investment by making those homes available to tourists eager to soak in the sunshine that characterizes Florida during most months of the year.



In addition to sand and surf, Sarasota possesses several cultural attractions. These include the Asolo Repertory Theatre as well as the Sarasota Ballet and the Sarasota Opera. For more than ten years, there has also been an annual film festival held in Sarasota. One of the more unusual cultural attractions in the city is the Sarasota Chalk Festival, an event that celebrates street painting.

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  • Sarasota, Florida
    The Next Best Place to Being on Siesta Key! Peaceful Sarasota vacation villas. Spacious villas Full Kitchens, W/D, Lanai, Garage, H-Pool, Jacuzzi, Tennis, BBQ, Beaches, Shopping, Restaurants & Golfing, Reunions, your R...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Villa
    $99 - $185 $693 - $1295 $2500 - $4263
  • Sarasota, Florida
    Prime location in 55+ gated community. Ground floor unit directly across from club house and heated pool.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Condo
    $0 - $0 $0 - $0 $1800 - $1800
  • Sarasota, Florida
    Siesta Canalfront Apartment.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Apartment
    $0 - $0 $0 - $0 $895 - $1495
  • Sarasota, Florida
    THIS PELICAN COVE BAY FRONT CONDO IS NEAR WORLD CLASS BEACHES, CLOSE TO SARASOTA WITH MANY FINE RESTAURANTS, THEATER AND SHOPPING...THE PROPERTY IS 75 ACRES ON LITTLE SARASOTA BAY. GATED, 6 POOLS, TENNIS, BOATING, KAYA...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
    $0 - $0 $0 - $0 $0 - $0
  • Sarasota, Florida
    Wonderfull 2/2 ground floor with private patio. Full ammenities. Clay tennis courts,kid pool,adult pool,fishing,BBQ,bike storage and fitness.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Centrally located in the heart of Sarasota, and only minutes away from our world famous Siesta Key Beach, Villa Espanola offers a bright and cheerful retreat with a heated swimming pool and a privately fenced backyard.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 House
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  • Sarasota, Florida
    Welcome to the Old Oak Cottage located just one and a half blocks from the north bridge to Siesta Key on the corner of Siesta Drive and Old Oak Road. This fabulous heated pool cottage is anything but ''old'' having been ...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 House
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  • Sarasota, Florida
    Welcome to the Harmony Cottage, a truly remarkable three bedroom, two bath cottage with an absolutely mesmerizing heated pool and spa.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 House
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  • Sarasota, Florida
    Centrally located in the heart of downtown Sarasota, and only minutes away from our Lido Key Beach, 1670 Laurel offers a modern and sophisticated peaceful retreat within walking distance to the vibrant Main Street of Sar...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 1 Condo
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  • Sarasota, Florida
    Just after you cross the North Bridge from the mainland onto fabulous Siesta Key and located in the coveted northern part of the Island among some of Siesta''s wealthiest homes lies a charming beach cottage called the &#...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    4 3 House
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  • Sarasota, Florida
      This property offers real-time booking and availability
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    2 2 Condo
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  • Sarasota, Florida
    Spacious and clean ~ south Siesta Key Condo! Second floor 2 bedroom, 2 bath condo with lovely Sarasota Bay view! Walk across the street for private beach access across the street. Just a few miles away from world fam...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Ground floor 2br 2b unit- Walk out your back door to grassy area and on to direct PRIVATE access to beach! Nicely furnished and with breezy lanai. leave the Hi-Rise behind and enjoy the easy access!
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Walk to everything!!!!This lovely duplex sleeps 6 on each side, and rents separately .Private beach access just one block away. Special gate access code for guests of this unit for private beach access, Walk to everyt...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 House
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  • Sarasota, Florida
    Gorgeous Bay View! This 5th floor unit is high above the trees to a beautiful view of Sarasota Bay.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Easy Access to ground floor unit, with gorgeous view of Sarasota Bay! Heated pool and private access to beach on Gulf side of Bay Tree Club. Quiet building and less traffic on south end of Siesta Key. Casual furnishing...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Condo
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  • Sarasota, Florida
    Siesta Key Gem! Steps from the #1 Beach in the Country!
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 House
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  • Sarasota, Florida
    Gorgeous Gulf front condo- with lots of UPGRADES! Granite Island in kitchen with wine refrigerator and stainless appliances. Extended remodeled living area, with hi-end window coverings. Private storage cabanas for eve...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Newly tiled corner unit on 2nd floor of quiet, and well established building on south Siesta Key! Many handmade wood furniture items in this condo. Comfortable and traditional styed furniture and lanai has futon for gu...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Ground floor condo, with upgraded finished in this 2br, 2b corner unit located in residential neighborhood. Located just 1/2 mile from public beach access. Pool on site, as well as laundry room for use of this 8 unit b...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Lovely corner unit GULF SIDE of Siesta - with tons of light! Well appointed with some upgrades. Washer and Dryer Stack in unit.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    True beach house directly on the beach. So Rare to find weekly rental in home with beach in your back yard! One bedroom beach cottage available to rent separately.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 House
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  • Sarasota, Florida
    Privacy! Perfect unit for big families or multiple couples. This floor 3br, 3b unit close to elevator and laundry. Double wide lanai with pool and greenbelt view.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 3 Condo
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  • Sarasota, Florida
    Darling one bedroom beach cottage a couple hundred feet from Point of Rocks Beach! Living/Dining combo, with sleeper sofa, and king sized bed in bedroom!
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Cottage
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  • Sarasota, Florida
    Ground floor condo one block from Crescent beach- sleeps 6! Two bedroom, Two bath, well equipped unit close to community pool. Clean and comfortable! Walk to everything you need!
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 House
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Villa
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  • Sarasota, Florida
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Centrally located in the heart of downtown Sarasota, and only minutes away from our Lido Key Beach, 1670 Laurel offers a modern and sophisticated peaceful retreat within walking distance to the vibrant Main Street of Sar...
      This property offers real-time booking and availability
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 1 Condo
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  • Sarasota, Florida
    Have you ever dreamed of vacationing near the beach? White sands of Siesta Key and Siesta Key Village are just a short distance, offering the islands shopping, dining and entertainment. This condo can sleep up to 7 guest...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 2 Condo
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  • Sarasota, Florida
    Nice quiet condo with walk in shower with a king bed in the Master Bedroom. Access to everything within a few blocks! Private outdoor patio for you to enjoy nature. A short walk to the beach.
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Condo
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  • Sarasota, Florida
    This Siesta Key 4 BR/3 BA pool cottage on the canal is guaranteed to take your breath away. Only 4 blocks from warm gulf waters and the white sands of Siesta Beach, and 1 block from Siesta Village with over 20 restaurant...
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    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    4 3 House
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