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Vacation Rentals in Longboat Key, FL

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All 134 Rentals in Longboat Key
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From
$193
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Inquiry
From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
8 photos Details Reviews (1) Make Inquiry
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details Reviews (2) Make Inquiry
Also consider
Soaring Spirits on Longboat Key updated 4 BR canal front pool home
4 Bedrooms, sleeps 7
$263 - $454 / night
Azure Dreams on Longboat Key Beach
5 Bedrooms, sleeps 10
$771 - $1,086 / night
Longboat Key Beachfront  - Inn on the Beach 1-207
2 Bedrooms, sleeps 6
$285 - $499 / night
Beachfront Villa w/ Private Pool & Stunning Views!
5 Bedrooms, sleeps 10
$1,000 / night
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 28, 2014
Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
5 of 5 stars Reviewed September 27, 2014
This property was wonderfully updated and maintained, single level, quaint and quiet. Right on the beautiful and uncrowded beach, yet close to grocery store, restaurants and local...
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From
$135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
18 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 18, 2014
My wife and I just came back from our best vacation ever! We have been to a lot of places in our life, but the Longboat Key is our #1 preference, it is heaven on earth! We loved...
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From
$105
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 24, 2014
So close to the beach, exactly what I was looking for. The studio was cozy and clean, cutely furnished. We loved the outdoor shower and will definitely return again!
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From
$162
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 2, 2014
We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details Reviews (12) Make Inquiry
4 of 5 stars Reviewed August 11, 2014
We were pleasantly surprised when we arrived at LaPlaya and entered our unit, which was very clean and nicely decorated. The staff was warm, friendly and very accommodating, too...
1 of 5 stars Reviewed April 2, 2014
We arrived to find the unit(102E) unclean, with old garbage and old food in the refrigerator, the linens had not been changed as there was old hair in the bed the comforter on the...
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From
$178
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
23 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed July 9, 2014
My sister and I stayed 3 nights here and wished we had it all week. This location was excellent for our morning walk/run exercise and the beach was beautiful! We saw a sea turtle...
5 of 5 stars Reviewed May 15, 2014
The 1 bedroom condo was very clean and just like posted pictures. 1st floor patio exit to beachfront was nice. I'm used to staying up higher and watching views from a balcony, but...
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From
$154
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
14 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed August 9, 2014
Everything was perfect for 2 people. Nice decor, room set-up and proximity to beach. Quiet, mostly private feel (except for renovations being done next door). easy to arrange the...
5 of 5 stars Reviewed July 21, 2014
My husband and I enjoyed everything about our stay in this beautiful condo. Not only did we have a nicely decorated room inside, but our view was amazing outside. We were able to...
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From
$179
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
14 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 28, 2013
Well kept and well located condo in a small comfortable complex. Right on beach and you can enjoy sunsets from your screened in porch. Many nice updates in kitchen, bedroom and...
5 of 5 stars Reviewed January 11, 2013
My family (Mother, husband, 2 teenage children) stayed in unit 118 of this condo for a week. The unit is fabulous, well stocked and right on the beach - gorgeous views all day...
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From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
35 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed July 4, 2014
This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
5 of 5 stars Reviewed February 28, 2014
Casa del Mar on Longboat Key is a beautifully landscaped property right on the beach. The grounds are carefully tended with lots of vine covered trellises, a flower and orchid...
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From
$149
Per Night
Studio, 1 Bathroom, Sleeps 5
16 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed September 29, 2013
Fantastic view and sunset. Beach clean and serene. Condo immaculate and updated. Suited our needs perfectly.
4 of 5 stars Reviewed November 16, 2011
We stayed in a ground floor unit, just steps from the beach. Unit was small, but had everything we needed. Bathroom was a little dated, but very clean. Kitchen well stocked and...
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From
$171
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
29 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 13, 2014
We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
5 of 5 stars Reviewed July 9, 2014
Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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From
$135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed September 22, 2014
If you think that Florida off-season cannot be enjoyable, think again! We have just spent 2 weeks in September, stayed in #303 and had a fabulous vacation. Below are some...
5 of 5 stars Reviewed August 20, 2014
It was the best vacation in last 20 years! Property location was great, just a few steps away from the beach and nice swimming pool. Unit was very clean, newly renovated...
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From
$3,800
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
7 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed April 28, 2014
I stayed here with my husband and daughter. The location was great as it is close to the bay and ocean. The neighborhood is quiet with nice neighbors. The peacocks in the...
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From
$157
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
16 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 13, 2014
I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
4 of 5 stars Reviewed May 12, 2014
This condo was just right for my husband myself and our young 18 mo. old daughter. The space was clean and bright. The resort pool and beach location on the Gulf was ideal. It...
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From
$2,500
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed April 2, 2014
the villa was clean and the appliances new . being able to have covered parking right next to the door was handy for unpacking and packing the car for our two month stay and...
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From
$186
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
26 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed July 2, 2014
My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at...
4 of 5 stars Reviewed May 6, 2014
Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
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From
$320
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 10, 2014
Beautiful suite overlooking a gorgeous beach, very comfortable & well equipped with high end features.
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From
$110
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
5 photos Details Reviews (12) Make Inquiry
5 of 5 stars Reviewed October 15, 2014
This condo had everything a person would want for a week or longer stay. The condo was clean and well decorated. My boyfriend and I enjoyed sitting on the balcony watching the...
5 of 5 stars Reviewed May 14, 2014
The unit was clean, and all needs were met. All things for a vacation was thought of, and perfectly provided. Cant beat the view and the value of this stay. Will be staying here...
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From
$500
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details Reviews (3) Make Inquiry
From
$1,650
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details Reviews (1) Make Inquiry
From
$117
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
47 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed August 8, 2014
You couldn't ask for anything more in a vacation retreat. Clean, modern, roomy accomodations. Steps to a white sand beach where the umbrellas and beach chairs are set up by the...
5 of 5 stars Reviewed August 10, 2013
We stayed here july 2013, and staying here was a pleasure ! The apartment was spacious , nicely decorated and well equipped with everything we – two pair and one little girl 3...
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From
$195
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details Reviews (18) Make Inquiry
5 of 5 stars Reviewed October 18, 2014
We just returned from our vacation at the Castle in the sky and are already talking about plans to return next year. Myself and 5 girlfriends decided to beach it for our informal...
5 of 5 stars Reviewed May 26, 2014
I rented this condo for three nights with family and friends. The condo is so comfortable with all the necessities needed to make your vacation as stress free as possible. My soon...
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From
$126
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed March 18, 2014
The cottage was well reflected by the pictures. Everything fairly new and clean. Beds comfortable, has everything. Area quiet but short drive to Bradenton and Holmes beaches, for...
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From
$3,500
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details Reviews (1) Make Inquiry
3 of 5 stars Reviewed January 5, 2014
would love to have the unit again if things are buffed up a bit. Second bedroom very musty and moldy? kitchen ok things work. Were installing new washer as we were leaving. And...
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From
$169
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details Reviews (1) Make Inquiry
2 of 5 stars Reviewed July 1, 2014
Check-in at Sand Cay was quick and easy, and the staff was friendly. We could clearly see the improvements the owners have been making, as some furniture and art work were very...
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From
$143
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
27 photos Details Reviews (1) Make Inquiry
1 of 5 stars Reviewed August 31, 2014
After a long flight from the UK and a 2.5 hour drive from Orlando we were pretty jaded and glad to have finally arrived at our destination, we were informed by the owners that an...
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From
$3,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
16 photos Details Make Inquiry
From
$350
Per Night
3 Bedrooms, 5 Bathrooms, Sleeps 9
19 photos Details Make Inquiry
From
$119
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
22 photos Details Make Inquiry
From
$63
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
23 photos Details Make Inquiry
From
$157
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
6 photos Details Make Inquiry
From
$1,800
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details Make Inquiry
From
$3,000
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details Make Inquiry
From
$2,550
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details Make Inquiry
From
$2,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details Make Inquiry
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Suitability

  • Wheelchair access (10)
  • Elder access (47)
  • Suitable for children (47)
  • Pet friendly (6)
  • Smoking allowed (1)

Amenities

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  • Air Conditioning (93)
  • Internet (88)
  • Other outdoor space (87)
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Book Online(56)

Suitability

  • Wheelchair access (10)
  • Elder access (47)
  • Suitable for children (47)
  • Pet friendly (6)
  • Smoking allowed (1)

Amenities

  • All pools (95)
  • Air Conditioning (93)
  • Internet (88)
  • Other outdoor space (87)
  • Public pool (80)
  • View all amenities
Beachfront condos and bayside villas – your vacation rental on Longboat Key

Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

Longboat Key - the upscale coastal vacation destination

This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

Cultural treasures along Sarasota Bay

Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

Waterfront dining

Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

Visitor reviews aid vacation rental selection

You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.