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Siesta Key Long Term Vacation Rentals(485)

485 Results
$1,045 - $2,400
per week
7 - 28 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 28 night min stay
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night min stay
(14)
$185 - $293
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night min stay
(40)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
6 - 7 night min stay
(28)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
(20)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(32)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
14 night min stay
(7)
$1,545 - $2,350
per week
7 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night min stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(55)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
6 - 7 night min stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night min stay
(50)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
1 - 29 night min stay
(7)
$900 - $1,480
per week
14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
14 night min stay
(3)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 3 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
28 - 30 night min stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(18)
$2,500 - $5,000
per month
30 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
30 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(35)
$193 - $207
per night
4 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
4 - 7 night min stay
(19)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(14)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
7 night min stay
(12)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
7 night min stay
(20)
$17,250 - $19,500
per month
30 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
30 night min stay
(14)
$185 - $285
per night
3 - 4 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 10
3 - 4 night min stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(12)
$1,045 - $1,745
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(18)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(8)
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Recent Siesta Key Reviews

Clean and convenient

5 of 5
This was our second year to return to this unit. We love it and will be back again next year. Everything is clean, and stocked to get you going. I would highly recommend you book this unit. Sandy Brennan
  • Submitted: May 19, 2015
  • Stayed: Apr 2015

We found our happy place!

5 of 5
My husband and I sold our house ,rented a house and built our new house all in a matter of six months.Needless to say we were a little stressed out and really needed a vacation to re group! But I'm hesitant to write this review because i don't everyone else to know what a awesome place it is (we will never be able to get a booking again) I call Siesta Key my happy place! The location is perfect,one block from the village and two blocks from the beach.We either walked or road bikes ,never using our car.The weather was perfect ,we would pack a lunch and go to the beach everyday .At night we would go back to the beach to watch the most amazing sunsets. What is so great about this place is you could choose either to grill and play cards by the pool at night or go into the village for dinner and listen to a band. The villa was well stocked and we had everything we needed for a comfortable stay, We defiantly would come back. We stayed for two weeks and wished we could have stayed longer, we love ,love, love, Siesta Keys!
  • Submitted: May 19, 2015
  • Stayed: Feb 2015

Perfect location for a Siesta Key beach vacation

5 of 5
The "big orange house" was the perfect setting for a girls week in lovely Siesta Key. The location could not have been more ideal - a short stroll into the village for coffee, shops, restaurants, farmers market, etc. The beach access is close as well - we counted steps at less than 900 (we were tracking using FitBits). The house provided everything we needed - linens, beach chairs, wagon (essential for pulling everything to the beach every day), cooler, and lots of space! We had 6 adults and fit fine into the 3 bedrooms, finding that 2.5 bathrooms was perfect. Laundry in the unit and a modern kitchen were super helpful and made it easy to settle in for the week. Arrival and departure instructions were clear and parking was easy - a true find in the village of Siesta Key:) We will DEFINITELY be back to stay in the orange house.
  • Submitted: May 17, 2015
  • Stayed: May 2015