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Longboat Key 2-bedroom Vacation Rentals, Apartments & More - 7 Rentals Available.

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7 Vacation rentals

Filters applied: 2+ Bedrooms

(2)

1 / 20

Longboat Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The Longboat Beach Club was a beautiful vacation location! The hotel room was the best I ever had. The beach was picture perfect, the food was excellent and the weather could not have been better. I thought I was vacationing in heaven! Thank you!...”
- Review left on 10/05/2015

$300

Very Good (2 reviews)

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from $300 / night

1 / 17

Longboat Key House

  • 6
  • 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$600

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from $600 / night

(1)

1 / 25

Longboat Key Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The condo is much larger and much more upscale then the pictures actually show. The location on the resort site makes for an excellent vacation, no noise, close to pool and fitness Center. The direction left by the owner re everything was exact and...”
- Review left on 01/04/2015

$58

Excellent (1 reviews)

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from $58 / night

(14)

1 / 13

Longboat Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Saubere, sehr gut ausgestattete und geschmackvoll eingerichtete Wohnung mit allem was man benötigt und noch vielem mehr. Im 2. Stock (= 3rd Floor in USA) gelegen, über eine Außentreppe direkt neben dem zur Wohnung gehörenden Parkplatz oder per...”
- Review left on 10/06/2016

$180

Very Good (14 reviews)

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from $180 / night

(1)

1 / 14

Longboat Key Townhouse

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$122

Excellent (1 reviews)

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from $122 / night

(1)

1 / 22

Longboat Key Condo

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017

$214

Very Good (1 reviews)

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from $214 / night

1 / 23

Longboat Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$94

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from $94 / night

Your search has been expanded 7.2 miles to include more rentals

1 / 11

Sarasota House - 2.7 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $240 / night

1 / 16

Bradenton House - 3.4 miles away

  • 3
  • 5
  • Min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly

$170

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from $170 / night

(3)

1 / 21

Bradenton Condo - 3.5 miles away

  • 2
  • 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“I recently spent a week at this lovely condo in Shorewalk Vacation Villas. It was very nice. Kitchen and living area were quite modern and well stocked and decorated. The bedrooms and bathrooms were a little dates but very clean and comfortable. The...”
- Review left on 10/19/2016

$110

Average (3 reviews)

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from $110 / night

(4)

1 / 46

Bradenton Beach Condo - 4.3 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning
“My family and I spent a week at this beautiful place. You never need to leave the island, it has everything. Trolleys and buses, but most everything is within walking distance. There are so many things to do, swimming, shelling, fishing, bike...”
- Review left on 07/06/2012

$170

Excellent (4 reviews)

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from $170 / night

1 / 21

Anna Maria Island Villa - 4.5 miles away

  • 2
  • 3
  • 1 night min
  • Child friendly

$175

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from $175 / night

1 / 20

Bradenton Beach Condo - 4.5 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$272

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from $272 / night

(4)

1 / 29

Bradenton Condo - 4.5 miles away

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$110

Excellent (4 reviews)

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from $110 / night

1 / 29

Cortez Townhouse - 4.6 miles away

  • 4
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$295

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from $295 / night

1 / 23

Bradenton Villa - 4.6 miles away

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$100

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from $100 / night

(2)

1 / 4

Cortez Cottage - 4.6 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Pet friendly
“This apartment had a beautiful open concept, nicely decorated. The place was supplied with nice quality furniture and cooking apparatus. Quiet and right on the canal, close to everything. Owners were above and beyond for help, and just a click...”
- Review left on 01/02/2015

$92

Very Good (2 reviews)

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from $92 / night

1 / 24

Bradenton Beach House - 4.6 miles away

  • 6
  • 14
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(2)

1 / 24

Bradenton Beach House - 4.6 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and friends and I rented this property to celebrate my bachelorette weekend and we picked the most perfect house possible! The layout of the house was ideal for accommodating a large number of guests in addition to providing comfortable...”
- Review left on 09/06/2016

$400

Excellent (2 reviews)

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from $400 / night

1 / 15

Bradenton Villa - 4.6 miles away

  • 2
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$100

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from $100 / night

(5)

1 / 93

Anna Maria Island House - 4.8 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$350

Excellent (5 reviews)

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from $350 / night

(6)

1 / 41

Bradenton Beach Condo - 4.8 miles away

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Mark, the owner, is very responsive in communications. He told us to just bring yourselves and everything is there, beach towel, beach chairs, towels, etc. Sure enough everything is there and in great condition. This condo complex has private...”
- Review left on 01/25/2016

$150

Excellent (6 reviews)

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from $150 / night

(11)

1 / 22

Bradenton House - 4.8 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile...”
- Review left on 04/07/2017

$129

Very Good (11 reviews)

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from $129 / night

(9)

1 / 72

Anna Maria Island Condo - 4.8 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$250

Excellent (9 reviews)

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from $250 / night

(28)

1 / 97

Bradenton Beach Condo - 4.8 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$250

Very Good (28 reviews)

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from $250 / night

(1)

1 / 20

Bradenton Beach Cottage - 4.9 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$150

Very Good (1 reviews)

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from $150 / night

(2)

1 / 20

Bradenton Beach Cottage - 4.9 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$135

Excellent (2 reviews)

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from $135 / night

1 / 81

Anna Maria Island Condo - 5 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200

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from $200 / night

(5)

1 / 92

Anna Maria Island Condo - 5 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$250

Very Good (5 reviews)

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from $250 / night

(2)

1 / 16

Sarasota Condo - 5.1 miles away

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$79

Very Good (2 reviews)

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from $79 / night

1 / 38

Bradenton Beach House - 5.2 miles away

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(68)

1 / 67

Bradenton Beach Cottage - 5.3 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We were suppose to go to West Palm Beach and the hurricane at that time changed our plans and we decided to look around at a place I had been to before--Anna Maria Island. We found this ad on the Sugar Shack and we were lucky it was not rented the...”
- Review left on 02/22/2017

$214

Excellent (68 reviews)

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from $214 / night

(7)

1 / 29

Anna Maria Island House - 5.4 miles away

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$400

Excellent (7 reviews)

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from $400 / night

(2)

1 / 11

Bradenton Apartment - 5.8 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$74

Excellent (2 reviews)

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from $74 / night

(4)

1 / 60

Bradenton Villa - 5.9 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We just returned from our stay in the Bayfront Villa. My husband, two teenagers and my 92-yr old Mother in law found this location to be perfect for us. My two kids thoroughly enjoyed fishing off of the dock, swimming in the pool and swimming off...”
- Review left on 06/23/2015

$213

Excellent (4 reviews)

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from $213 / night

(1)

1 / 16

Bradenton Condo - 6.1 miles away

  • 3
  • 6
  • 90 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Ask about children
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$60

Very Good (1 reviews)

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from $60 / night

1 / 29

Anna Maria House - 6.1 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

from $141 / night

(1)

1 / 19

Holmes Beach Cottage - 6.3 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We couldn't have asked for a better AMI rental. I've stayed at others, but have finally found one I will stay at again (and again!) Don't worry about not being directly on the beach, because you are just a few steps away! It was wonderful to have our...”
- Review left on 04/07/2016

$271

Excellent (1 reviews)

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from $271 / night

(3)

1 / 25

Anna Maria Island Condo - 6.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$143

Excellent (3 reviews)

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from $143 / night

(21)

1 / 11

Holmes Beach Townhouse - 6.7 miles away

  • 2
  • 6
  • Min stay varies
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$150

Very Good (21 reviews)

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from $150 / night

(7)

1 / 84

Anna Maria Island Condo - 6.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Impeccable beach house! All the amenities one would want. Great Weber gas grill, (almost) private pool, brand new kitchen, brand new front loader washer/dryer (free). Cross the street and you're on the public beach, or drive 10 min north or south...”
- Review left on 11/23/2016

$250

Excellent (7 reviews)

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from $250 / night

(1)

1 / 44

Anna Maria Island Condo - 6.9 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was our first time renting, we usually stay at a hotel. The unit was exactly like the photos and clean as well. I had some trouble with the garbage disposal so I called the property management and they were very professional and offer to put...”
- Review left on 07/05/2016

$150

Excellent (1 reviews)

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from $150 / night

1 / 53

Holmes Beach House - 6.9 miles away

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $350 / night

1 / 26

Bradenton House - 6.9 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $158 / night

(17)

1 / 77

Anna Maria Island Cottage - 7 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and I spent a week in the cottage and surrounding Anna Maria Island.We had a very relaxing vacation by the sea and enjoyed every ammentity the cottage offered.The comforts were those of our own home. Sheila was a perfect host indeed for any...”
- Review left on 08/18/2016

$186

Excellent (17 reviews)

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from $186 / night

(2)

1 / 31

Holmes Beach House - 7.2 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Ask about pets

$109

Very Good (2 reviews)

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from $109 / night

(6)

1 / 16

Holmes Beach Villa - 7.2 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$329

Excellent (6 reviews)

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from $329 / night