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Longboat Key Vacation Rentals & Apartments with Swimming Pool - 8 Rentals Available.

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8 Vacation rentals

Filters applied: Swimming pool

(15)

1 / 72

Longboat Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 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

$115

Excellent (15 reviews)

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from $115 / 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

$59

Excellent (1 reviews)

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from $59 / 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

(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

(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

1 / 10

Longboat Key Townhouse

  • 3
  • 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $334 / 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

1 / 14

Longboat Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $83 / night

Your search has been expanded 7 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

(4)

1 / 5

Bradenton Condo - 4.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Michelle was so helpful and willing to meet all our our expectations and needs. The location of her condo is so convenient. It is close the YMCA, Publix, Walmart, Home Depot, excellent restaurants, and many more. We would consider staying there...”
- Review left on 03/05/2017

$95

Excellent (4 reviews)

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from $95 / night

(2)

1 / 24

Bradenton Condo - 4.5 miles away

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

$110

Excellent (2 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

(7)

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 (7 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

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

(67)

1 / 67

Bradenton Beach Cottage - 5.3 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had a girlfriends getaway and stayed at the Sugar Shack; our second time to stay. Sheila has made great updates to the Sugar Shack, the bathrooms have been remodeled, the kitchen has been updated, the third bedroom has been remodeled and the...”
- Review left on 11/23/2014

$214

Excellent (67 reviews)

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from $214 / night

(6)

1 / 29

Anna Maria Island House - 5.4 miles away

  • 4
  • 8
  • 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

$390

Excellent (6 reviews)

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from $390 / 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

(10)

1 / 11

Sarasota Guest house - 5.7 miles away

  • 1
  • 3
  • 7 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Air conditioning
“My husband and I rented the month of December so that we could spend time with family who live in Sarasota. Our New York daughter spent a week at the cottage with us. We so enjoyed the privacy, comfortable cottage and pool. It was wonderful having a...”
- Review left on 01/02/2016

$93

Excellent (10 reviews)

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from $93 / night

(15)

1 / 19

Sarasota House - 5.7 miles away

  • 3
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I have been traveling for a long time and stayed in many Hotels but there is nothing like staying in this home. The owner Jaye has made this place so much like home. There was every possible amenity you could think of. She did not leave any stone...”
- Review left on 05/09/2016

$100

Excellent (15 reviews)

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from $100 / night

(1)

1 / 11

Bradenton Apartment - 5.8 miles away

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

$74

Excellent (1 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)

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

$143

Excellent (1 reviews)

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from $143 / night

(3)

1 / 25

Anna Maria Island Condo - 6.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • 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

$142

Excellent (3 reviews)

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from $142 / night

(20)

1 / 11

Holmes Beach Townhouse - 6.7 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 (20 reviews)

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from $150 / night

1 / 24

Holmes Beach House - 6.7 miles away

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $350 / night

(4)

1 / 30

Anna Maria Island House - 6.9 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home is exactly as pictured and the owners are so great to work with! We loved all the accommodations of the home and it was very, very clean and well maintained! It had everything we needed to enjoy both the pool and the beach. With 3...”
- Review left on 11/07/2016

$214

Excellent (4 reviews)

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from $214 / night

(1)

1 / 78

Anna Maria Island Condo - 6.9 miles away

  • 1
  • 3
  • Min stay varies
  • 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

(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