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Longboat Key Vacation Rentals & Apartments with Swimming Pool - 40 Rentals Available.

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40 Vacation rentals

Filters applied: Swimming pool

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(5)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Had an excellent time! Unit was clean and precisely as described. Great location on Siesta Key with a short walk for Groceries, Food and Libations. Beach was a 5min walk across the street (using the signaled crosswalk) through the beachside section...”
- Review left on 03/13/2017

$88.00

Excellent (5 reviews)

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from $88.00 / night

(26)

1 / 24

Siesta Key Condo - 9.8 miles away

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland...”
- Review left on 07/14/2014

$147.00

Excellent (26 reviews)

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from $147.00 / night

(38)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We...”
- Review left on 01/02/2013

$88.00

Excellent (38 reviews)

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from $88.00 / night

(12)

1 / 23

Bradenton House - 14.1 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$279.00

Excellent (12 reviews)

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from $279.00 / night

(4)

1 / 19

Bradenton Villa - 14.4 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$180.00

Excellent (4 reviews)

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from $180.00 / night

(4)

1 / 29

Bradenton Condo - 6.4 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 45 minutes

$63.00

Excellent (4 reviews)

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from $63.00 / night

1 / 13

Lakewood Ranch House - 10.7 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

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from $279.00 / night

(9)

1 / 13

Ellenton House - 14.2 miles away

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Lovely house great setting 5 minute walk to the pool. Quiet complex friendly people. 5 minute drive to 301 for start of shops k Mart, Public, Brand name outlets and Wal-Mart, Post Office and Banks. Many restaurants on door step too. Beach approx 40...”
- Review left on 11/11/2016

$115.00

Excellent (9 reviews)

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from $115.00 / night

(25)

1 / 24

Bradenton House - 11.1 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 35 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (25 reviews)

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from $150.00 / night

(7)

1 / 38

Siesta Key House - 8.3 miles away

  • 5
  • 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$516.00

Excellent (7 reviews)

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from $516.00 / night

(12)

1 / 40

Siesta Key Condo - 8.6 miles away

  • 2
  • 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”
- Review left on 01/06/2017

$89.00

Excellent (12 reviews)

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from $89.00 / night

1 / 32

Bradenton Villa - 6.4 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 54 minutes

$115.00

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from $115.00 / night

(23)

1 / 29

Anna Maria House - 12.4 miles away

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 3 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$201.00

Very Good (23 reviews)

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from $201.00 / night

1 / 41

Sarasota House - 7.7 miles away

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$300.00

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from $300.00 / night

1 / 33

Siesta Key Condo - 10.1 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children

$228.00

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from $228.00 / night

(30)

1 / 10

Sarasota Guest house - 4.7 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$148.00

Excellent (30 reviews)

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from $148.00 / night

1 / 26

Bradenton House - 9.6 miles away

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

$158.00

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from $158.00 / night

1 / 30

Bradenton Villa - 6.4 miles away

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

Responds fast! Avg. 1 hour 54 minutes

$75.00

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from $75.00 / night

1 / 8

Sarasota Condo - 4.4 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

$57.00

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from $57.00 / night

(5)

1 / 92

Anna Maria Island Condo - 8.5 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

$266.00

Very Good (5 reviews)

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from $266.00 / night

(25)

1 / 24

Sarasota Condo - 8.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Not only is the location perfect, but the condo is more then perfect! Everything we needed for a week at the beach including beach chairs... towels etc! Couldn't have been a better vacation! Can't wait to book again... THANKYOU STEVE...”
- Review left on 10/17/2017

$190.00

Excellent (25 reviews)

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from $190.00 / night

(2)

1 / 16

Sarasota Condo - 4.4 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“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

$114.00

Very Good (2 reviews)

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from $114.00 / night

(7)

1 / 47

Sarasota House - 10.9 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Ask about children
“This is our fourth or fifth year that we have come to the villa in December we absolutely love it . There is so much to do there are tennis courts & communal pool, there is a mall around the corner plenty of publix & a short drive to the beach. The...”
- Review left on 12/29/2016

$100.00

Very Good (7 reviews)

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from $100.00 / night

(9)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
“We recently spent a week in Siesta Key, our fourth year in a row making this our Fall vacation spot. This year, we we fortunate to find an available week at Sandy' Siesta that matched out travel plans. What a great spot! A short walk to the...”
- Review left on 12/16/2016

$130.00

Excellent (9 reviews)

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from $130.00 / night

1 / 16

Bradenton House - 4.6 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$155.00

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from $155.00 / night

1 / 21

Sarasota House - 7.7 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$150.00

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from $150.00 / night

(21)

1 / 13

Sarasota Condo - 9.9 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“First time staying at this condo, and we were not disappointed! It was very clean and nicely decorated! It had everything that we needed for our week stay. The location was great! Close to the beach, pool, stores and Captain Curt's, which is a...”
- Review left on 11/28/2016

$87.00

Excellent (21 reviews)

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from $87.00 / night

1 / 7

Sarasota Condo - 12.6 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 18 minutes

$204.00

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from $204.00 / night

(5)

1 / 24

Bradenton Cottage - 6.4 miles away

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“While visiting my youngest daughter in Bradenton I booked a week stay at Arbor Terrance in one of their one bedroom cottage. The one bedroom cottage was very nice, well maintained and conveniently located to shopping centers and points of interest...”
- Review left on 10/16/2015

$150.00

Excellent (5 reviews)

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from $150.00 / night

1 / 12

Bradenton House - 9.8 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$246.00

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from $246.00 / night

(8)

1 / 84

Anna Maria Island Condo - 10.3 miles away

  • 2
  • 6
  • 7 nights min
  • 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

$396.00

Excellent (8 reviews)

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from $396.00 / night

1 / 14

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$114.00

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from $114.00 / night

(18)

1 / 12

Bradenton House - 14.4 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Superbly equipped villa in a great location. Immaculately clean with high spec kitchen which was equipped extremely well with good quality appliances. Pool area nice with fab spa overlooking lake and big outside dining area which was used all the...”
- Review left on 08/07/2016

$279.00

Excellent (18 reviews)

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from $279.00 / night

(2)

1 / 25

Holmes Beach Townhouse - 12.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$299.00

Excellent (2 reviews)

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from $299.00 / night

(6)

1 / 22

Siesta Key Condo - 7.5 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 59 minutes

“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”
- Review left on 12/15/2015

$146.00

Excellent (6 reviews)

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from $146.00 / night

(29)

1 / 87

Bradenton Beach Condo - 8.3 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

$344.00

Very Good (29 reviews)

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from $344.00 / night

(16)

Certificate of Excellence

1 / 26

Anna Maria Island House - 8.9 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 12 minutes

Certificate of Excellence

“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

$516.00

Excellent (16 reviews)

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from $516.00 / night

(1)

1 / 39

Siesta Key House - 10.2 miles away

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

$395.00

Excellent (1 reviews)

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from $395.00 / night

1 / 53

Holmes Beach House - 10.3 miles away

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

$599.00

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from $599.00 / night

(2)

1 / 23

Siesta Key House - 8.2 miles away

  • 4
  • 12
  • 7 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$682.00

Excellent (2 reviews)

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from $682.00 / night