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Longboat Key Vacation Rentals & Apartments with Swimming Pool - 6 Rentals Available.

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6 Vacation rentals

Filters applied: Swimming pool

(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

(1)

1 / 49

Longboat Key House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Our Stay at the Conrad Cabana on Longboat Key was more than we had wished for. The moment we entered the home we knew that we would be very comfortable and we were. Throughout the rental process everything went smoothly and when we arrived we were...”
- Review left on 02/21/2016

$400

Excellent (1 reviews)

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from $400 / night

(13)

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 (13 reviews)

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from $180 / night

(15)

1 / 48

Longboat Key Condo

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“The two balconies and lanai overlooking the fabulous Gulf of Mexico provid a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably furnished with wifi and 3 TV's. Every convenience has been thought of, from...”
- Review left on 04/07/2015

$79

Excellent (15 reviews)

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from $79 / night

(1)

1 / 24

Longboat Key Apartment

  • 2
  • 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our first time to Longboat Key,Florida. This condo was adorable and in a great location! We arrived at night and once we unlocked the door were so relieved. It is a quaint 2 bedroom 1 bath condo that was so clean and lovely furnishings. We...”
- Review left on 04/11/2016

$135

Very Good (1 reviews)

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from $135 / night

(5)

1 / 44

Longboat Key House

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house is stunning, but that is nothing compared to the location! Right on the beach, beautiful views! Kids loved the pool while the adults loved the relaxation. I can't think of anything negative to say...we truly enjoyed our time at the house...”
- Review left on 02/09/2017

$800

Excellent (5 reviews)

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from $800 / night

Your search has been expanded 8 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 / 12

Bradenton House - 3.4 miles away

  • 3
  • 6
  • Min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly

$200

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from $200 / night

(3)

1 / 29

Bradenton Condo - 4.5 miles away

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

$110

Excellent (3 reviews)

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from $110 / night

1 / 16

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

1 / 24

Bradenton Beach House - 4.6 miles away

  • 6
  • 13
  • Min stay varies
  • 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

(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
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

(8)

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 (8 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 / 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

$200

Very Good (5 reviews)

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from $200 / night

1 / 38

Bradenton Beach House - 5.2 miles away

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(9)

1 / 22

Bradenton Beach Cottage - 5.2 miles away

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Good location. Clean, well supplied, good daily maid service. Not much area for being pet friendly for bathroom and for walking dog. Parking lot flooded with minimal rain. No overhang on porch at door or over chairs to get out of rain to even enjoy...”
- Review left on 08/08/2016

$155

Very Good (9 reviews)

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from $155 / 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

(6)

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

$365

Excellent (6 reviews)

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from $365 / night

(4)

1 / 16

Bradenton House - 5.5 miles away

  • 3
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Was so hard finding a house that met the needs of our family of 10. But, Cappobianco's family just went above and beyond with this beautiful and super completed house, I called Paradise! Can't thank them enough for allowing us to spend our family...”
- Review left on 06/16/2016

$243

Excellent (4 reviews)

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from $243 / 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

(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)

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

(1)

1 / 78

Anna Maria Island Condo - 6.9 miles away

  • 1
  • 3
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$120

Excellent (1 reviews)

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from $120 / 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 / 24

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 / 13

Sarasota House - 7.4 miles away

  • 2
  • 3
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We only stayed one week but completely enjoyed the experience. The house is very comfortable, in a nice neighborhood just blocks from the beach and has a nice lap pool in the back. We particularly liked the nice walks in the mornings and the...”
- Review left on 12/17/2016

$120

Average (2 reviews)

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from $120 / night

(1)

1 / 47

Holmes Beach House - 8 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“As beautiful as it looks in the photos, I actually think it's better in person. I literally want to live there. The house is so spacious, features a great open floor plan for family time, and offers 4 master bedrooms, spread out on 2 floors to...”
- Review left on 04/26/2016

$555

Excellent (1 reviews)

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from $555 / night

(2)

1 / 20

Holmes Beach Townhouse - 8 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed this house. It was just a short walk to the beach. It was the perfect size for our family of four. The decorations were very pretty and beachy! The pool and outside landscaping was gorgeous! It came supplied with a beach wagon which was a...”
- Review left on 04/21/2016

$236

Excellent (2 reviews)

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from $236 / night

1 / 24

Holmes Beach House - 8 miles away

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $400 / night

(1)

1 / 24

Holmes Beach Townhouse - 8 miles away

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Slept 13 comfortably. Great location and pool was a lifesaver with smaller children. I would highly recommend this property...”
- Review left on 07/21/2016

$300

Excellent (1 reviews)

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from $300 / night

(2)

1 / 18

Holmes Beach House - 8 miles away

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We had a wonderful vacation. Absolutely loved this rental home. Everything you need is there. My family loved the pool and having beach chairs & sand toys on hand was an added bonus. Can't wait to book our next vacation in the same home...”
- Review left on 05/04/2016

$250

Excellent (2 reviews)

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from $250 / night