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Vacation rentals in Siesta Key

Vacation rentals in Siesta Key

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Top-rated holiday rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Stroll to Siesta Beach from Serene Condo + 2 bikes
    SUPERHOSTEntire apartment · 4 guests · 1 bed · 1 bathroom
    Stroll to Siesta Beach from Serene Condo + 2 bikes

    Relax in your ultra-private corner unit condo with amazing natural light & contemporary decor +private lanai. Enjoy the soft white sand & tropical vibes at Siesta Key Beach. This condo is located on the east side of Midnight Pass Rd, with the open air trolley stop out front *please note there is not direct private beach access: -beach wagon & gear -BIKES ($30 per bike entire stay) -Pool -closed until April 30th -Reserved parking -Washer & Dryer -Tennis courts/Dock

    What guests are saying:

    “Jayme was quick to respond, check in was easy, the apartment was clean and the bed is very soft and comfy. The location is great if you don't mind a bit of a walk to the beach. The trolley is great when it's running. But unfortunately it wasn't running memorial day wknd yet. We had a great stay and the bikes were nice too. All you need for a lovely weekend!”

  • Siesta key getaway!
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bathroom
    Siesta key getaway!

    perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

    What guests are saying:

    “Debbie’s place was the perfect space for my weekend getaway. The condo is in a great location, very comfortable and had everything I needed. It was really easy to get to and to get around the key from. Debbie was a great host and I would recommend her place to anyone.”

  • 5209B Calle Menorca - Amazing Pool or Siesta Key Beach?  You Choose with this Perfectly Located Condo in Siesta Key Village
    SUPERHOSTEntire apartment · 4 guests · 3 beds · 2 bathrooms
    5209B Calle Menorca - Amazing Pool or Siesta Key Beach? You Choose with this Perfectly Located Condo in Siesta Key Village

    This is the vacation you've been waiting for! 5209 B Calle Menorca is one of four newly purchased and renovated condos in the heart of Siesta Key Village. This is a second floor unit and requires climbing stairs. The interior is tastefully furnished with a bright beachy feel and the exterior was finished in November 2018 with two new pools and a tiki bar. Make your reservations fast because these will not remain available for long, especially in prime season. Bedroom 1-1 King Bed (Sleeps 2) Bedroom 2-2 Twin Beds (Sleeps 2) THE SIESTA BEACH RENTALS ADVANTAGE All photos, calendar dates, and rates on this website are 100% accurate. All of our homes include cable TV, Wi-Fi, quality linens, beach towels, chairs and umbrellas. Our kitchens are stocked and include pots, pans, plates, silverware, glasses, coffee mugs and other items. We make it easy to stay with us! Drive straight to your rental and access the home with your unique lock code. We will send you detailed check-in instructions 48 hours prior to arrival, and we are available 24 hours a day with live help should you require it. Siesta Beach Rentals follows local/state tax rules. Each reservation includes applicable taxes and fees. *Taxes & Fees not included. *Check In / Check Out-Strictly Saturday to Saturday during Prime season. Call directly to negotiate options during Summer and Winter seasons. *Prime Season rates may apply for certain holidays. *Late Summer Season rates negotiable. Prime Season Jan 31-Apr 30 $2,500 wk / $10,000 mo Summer Season May 1-Dec 14 $1,500 wk / $6,000 mo Winter Season Dec 15-Jan 30 $2,000 wk / $7,600 mo

    What guests are saying:

    “This place is exactly as pictured and even better in person. Truly a very clean place with modern decor and spacious areas. The bed was very comfortable. Having beach chairs, towels and even a couple of beach wagons available for use was great since we went to the beach every day to enjoy beautiful Siesta Key Beach and the great weather we had while there! Be sure to bring your own toiletries and hair dryer which aren’t provided and is stated in the listing. I really couldn’t find any negatives, but if I had to it would be the water pressure isn’t the best for washing longer hair but it worked out. You have your own washer and dryer conveniently outside your door. Market to buy just about anything is just a 2 minute walk at the end of the street. Restaurants and shops of Siesta Key Village is right around the corner literally when you get to the end of the street. The beach is about a 10 minute easy walk a couple blocks away. I’d definitely stay at this place again! Beach with restrooms and concessions is just a mile or so drive south and lots of free parking. Wonderful clean beach and the softest white sand you’ll ever feel on your feet.”

Holiday rentals for every style

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Popular amenities for Siesta Key holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Siesta Key

Adorable studio close to Siesta beach!
SUPERHOSTEntire guest suite
Adorable studio close to Siesta beach!
Price:₹4,499 / night
Cozy Cottage on Siesta Key
SUPERHOSTEntire cottage
Cozy Cottage on Siesta Key
Price:₹7,073 / night
Beachfront Condo! Shown on HGTV! Renovated in 2018
SUPERHOSTEntire apartment
Beachfront Condo! Shown on HGTV! Renovated in 2018
Price:₹7,799 / night
Beach & Pool Open! Direct Beachfront. Sunset View!
SUPERHOSTEntire flat
Beach & Pool Open! Direct Beachfront. Sunset View!
Price:₹19,210 / night
Cozy Private Bungalow with Shared Pool Access
SUPERHOSTEntire guest house
Cozy Private Bungalow with Shared Pool Access
Price:₹6,387 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire apartment
Bright and Beachy - Steps to the Water!
Price:₹14,622 / night
Private Beach Siesta Key   Resort Jamaica Royale
SUPERHOSTEntire apartment
Private Beach Siesta Key Resort Jamaica Royale
Price:₹14,301 / night
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Entire villa
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Price:₹14,997 / night
Heart of Siesta Key Village - Walk to Beach
SUPERHOSTEntire apartment
Heart of Siesta Key Village - Walk to Beach
Price:₹10,873 / night
Siesta Key Condo with 2 QUEEN BEDS, Walk to Beach
SUPERHOSTEntire apartment
Siesta Key Condo with 2 QUEEN BEDS, Walk to Beach
Price:₹6,674 / night
Siesta Key SunBum Studio; Steps to Sand
SUPERHOSTEntire apartment
Siesta Key SunBum Studio; Steps to Sand
Price:₹11,887 / night
2-Floor,  2BR, 3Bath, Condo Sleeps 8 - Near Beach!
SUPERHOSTEntire apartment
2-Floor, 2BR, 3Bath, Condo Sleeps 8 - Near Beach!
Price:₹7,961 / night
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