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Longboat Key Vacation Rentals

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[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:30
Available 4/1. ENJOY: Top floor gulf side beach front & view condo. Private white sand beach. Sun umbrellas & lounges. 8 breezy Har-Tru tennis courts. Study ...
  • Nightly
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  • Weekly
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  • Monthly
    $2,100 - $6,000
Management: Verified owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Min stay:7
Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a loft, 3 full ...
  • Nightly
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  • Weekly
    $1,500 - $1,800
  • Monthly
    $4,500 - $5,950

The following rentals are within 25 miles of Longboat Key, Florida.

Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:6
This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the ...
  • Nightly
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  • Weekly
    $1,260 - $1,350
  • Monthly
    $4,900 - $5,900
Contact Manager
Nightly rate from
$150
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 10
Bathrooms: 2
Relax in a heated private pool that has a partial view of Roberts Bay. Our Venice Florida Baycrest II home is a wonderful 3 bedroom, 2 bathroom house located ...
  • Nightly
    $150 - $250
  • Weekly
    $795 - $1,795
  • Monthly
    $3,387 - $6,011
Villa 21, Sarasota
Contact Manager
Nightly rate from
$144
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 4
Bathrooms: 2
Island House Beach Resort - Siesta Key Florida, Crescent Beach. This large 2 bedrooms, 2 bath villa is 1000 sq. ft. It has a large living area, dining area, ...
  • Nightly
    $144 - $227
  • Weekly
    $1,008 - $1,589
  • Monthly
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Management: Verified Plus owner
Property: Villa
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:1
"Island Garden Villas is the most enchanting spot on Anna Maria Island." Imagine yourself surrounded by lush tropical gardens with the soft sounds of water ...
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  • Weekly
    $895 - $1,250
  • Monthly
    $2,850 - $3,350
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 14
Bathrooms: 2
West of Gulf Drive Wedding Friendly property -- (4) Bed: (2 shower only) Bath: Accommodates up to (14) people: King, 2 Queens, 4 Twins, queen air and 2 twin ...
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Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
Min stay:7
The Bayshore Garden Home is an executive level, bay front home featuring four bedrooms and two and one half baths located at 3204 Bay Drive in Bradenton. A ...
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  • Weekly
    $1,295 - $1,890
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PROP ID 621, Bradenton
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Min stay:7
CLICK HERE FOR A VIDEO TOUR http://66.135.33.137/apps/csafytemh1o4nbtwuxyt/player_20090831202239/player.html Sabal Harbour is a beautiful landscaped, ...
  • Nightly
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  • Weekly
    $1,270 - $1,378
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Contact Manager
Nightly rate from
$150
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 10
Bathrooms: 2
Our Aurora Seabreeze house on the Island of Venice is a roomy 3 bedroom house with a brand new electric heated pool and screened in patio. Our house sleeps 10 ...
  • Nightly
    $150 - $250
  • Weekly
    $795 - $1,795
  • Monthly
    $3,387 - $6,011
2 South, Sarasota
Contact Manager
Nightly rate from
$186
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 7
Bathrooms: 2
Island House Beach Resort!!Ground Floor, Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the ...
  • Nightly
    $186 - $298
  • Weekly
    $1,302 - $2,086
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Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 3
Treat yourself to an unforgettable vacation at one of our welcoming beachfront homes on beautiful Anna Maria Island, Florida. We have five Gulf-front condos ...
  • Nightly
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  • Weekly
    $2,995
  • Monthly
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Contact Manager
Nightly rate from
$150
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any ...
  • Nightly
    $150 - $300
  • Weekly
    $895 - $1,795
  • Monthly
    $2,898 - $5,296
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
Charming Key West style cottage with secluded garden pool on the desirable north end of the island. Owner was a member of the opening team of the San ...
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  • Weekly
    $1,600 - $2,500
  • Monthly
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Longboat Key Vacation Rental Advice
Posted by GAteach, Oct 30, 2009
... seems that many of the rental homes are ... ... at the beach? We plan to be there late May or early June. If anyone has rented a three bedroom home with a pool and would recommend the rental, please do so. We would also consider a condo, preferably oceanfront or oceanview ... more
Posted by cbchrc, Oct 30, 2009
... permanently. We rented from Florida Vacation Connection (www.flvacationconnection.com) and were completely satisfied each time. Their properties are excellent and their service is good as well; they are very responsive if you ever have any problems. As for distance from the beach, unless you are on the Bay side ... more
Posted by GAteach, Oct 31, 2009
... As a teenager, I lived in the Bahamas for four years. Since then, I long for turquoise water. I drove through the islands near Sarasota a few years ago, and they reminded me of the Bahamas years ago. I made a mental note that I would return for a vacation ... more
Posted by SRQgirl, Jun 27, 2009
... pm,May 23, 2009 Many rental places have started their promotions for the off-season. I received a mailing today for three places on Longboat: Turtle Crawl Inn, The Beach, and Silver Sands. It said that you could pay for 3 nights and get a 4th night free anytime between ... more
Posted by Pat_Picks, Jun 28, 2009
We discovered Silver Sands ourselves for a less-than-a-week vacation last January through a vrbo.com listing. We stayed in a 1-bedroom beachfront condo at a great rate; it was vrbo #210777. ... more
Posted by SRQgirl, May 31, 2009
How long will you be staying? Some places have a minimum rental period. You should be able to find something in a reasonable price range. September is very off season in this area...~SRQgirl ... more
Posted by vikkit, Jun 2, 2009
... be able to stretch our vacation out a ... ... you know where we end up. I don't ever travel without checking with TA forums...it made our trip to Kauai last year the best it could be and I'm sure it will make out LBK vacation just as nice ... more
Posted by cbchrc, Apr 29, 2009
... Sea Club III (Wedebrock had rentals there at one point; Wagner Realty may have one now). Or near mid-Key, see if you can find a house rental in the Buttonwood area (Buttonwood or Longview). In the past I used Vacation Connection to rent a wonderful house on Buttonwood several ... more
Posted by SRQgirl, Apr 23, 2009
According to their website, it appears Beach Place has a 1 month minimum rental.. http://www.beachplacelbk.com/ ~SRQgirl ... more
Posted by SRQgirl, Apr 23, 2009
A rental at Beach Place: http://www.vacationrentals411.com/vacation/4011.html ~SRQgirl ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns