Luxury Vacation Rentals in Siesta Key

(11 rentals)
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Siesta Key House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
9 reviews
last minute deal
LAST MINUTE DEAL 4/25 - 5/17: Weeks starting Apr 25 & May 10 One night free at amazing unique location on Siesta Key 15% discount

$790

avg/night

$790
avg per night
Offer for: Apr 25 - May 17:
Weeks starting Apr 25 & May 10 One night free at amazing unique location on Siesta Key 15% discount

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Hurricane Update: We lucked out! Hurricane Helene did not flood our beach house except for the carport. We need to replace the hot water heater, the washer and dryer, and some walls and doors made of wood. Hurricane Milton damaged some soffits but they have already been repaired.A front row seat ...

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Property Type

Siesta Key House

Featured review

"Perfect location! Wonderful accommodations!"

Booked this spot for the first time and spent a wonderful week there with my three sisters for a birthday celebration. The weather was great and the beach and water were everything we had hoped it would ...

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DEAL
Siesta Key Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

$800

avg/night

$800
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky ...

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Property Type

Siesta Key Condo

Featured review

"Heaven"

I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps ...

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Siesta Key Estate
6 BR | 5 BA | Sleeps 20 | Quick View
Sleeps 20, 6 bedrooms, 5 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key Beach

$796

avg/night

$796
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach. It is perfect for large groups or reunions as this house includes separate living spaces and has a total of 13 beds. Right behind the main house, you will find a fun area to relax, play ...

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Property Type

Siesta Key Estate

Featured review

"A perfect vacation!"

This is a wonderful 5 plus star accommodation! The location is perfect, so convenient to the beach and so many things to do. The house is stocked with everything you need and more. Michael is an excellent ...

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Siesta Key House
5 BR | 4 BA | Sleeps 13 | Quick View
Sleeps 13, 5 bedrooms, 4 bathrooms
13 reviews

Distance to beach: 400 feet to Siesta Beach

$812

avg/night

$812
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

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Property Type

Siesta Key House

Featured review

"Amazing home!"

We had an amazing time with our family at this home in SK! David (property manager) was incredibly responsive to our questions and even stopped by to introduce himself when we arrived!The space was ...

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Siesta Key Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$829

avg/night

$829
avg per night
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Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

***LAST MINUTE DEAL! 20% OFF WEEKLY STAYS FOR THE MONTH OF JANUARY 2025 .This lovely penthouse condo is in one of Siesta Key's newest complexes (built in 2006). The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
5 BR | 3.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3.5 bathrooms

$823

avg/night

$823
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This 3600 sq ft., 5 Bedroom 3.5 Bath, Townhome Offers, Private heated pool, ** Please be aware that the pool is refreshing, but has limited space for larger parties. many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. LAYOUT of the HOUSE : Ground floor off the pool ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
5 BR | 3.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 3.5 bathrooms

$894

avg/night

$894
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 3400 sq ft., 5 Bedroom 3 Bath, Townhome Offers, Private heated pool- **please keep in mind the pool is refreshing, but has limited space for larger parties. Many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. It has a patio and 2 car garage. 2nd Floor is Living ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$714

avg/night

$714
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

*** MARCH SPECIAL- MARCH 15-31 $9000 PLUS FEES AND TAXES!!!*** EXPERIENCE LUXURY AT IT'S FINEST IN THIS STUNNING 2ND FLOOR CONDO WITH PARTIAL GULF VIEW FROM SIDE BALCONY. BACK PATIO OPENS UP TO ONE OF THE TWO POOLS AND FEATURES A GORGEOUS OUTDOOR KITCHEN. KITCHEN HAS GRANITE COUNTERTOPS, STAINLESS ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$807

avg/night

$807
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

**Any advertised discounts on website do not apply to this unit*** THIS 2ND FLOOR LUXURY CONDO HAS ONCE AGAIN BEEN UPDATED WITH DESIGNER FURNITURE AND FURNISHINGS. ALL BEDS NOW HAVE 800 COUNT VERA WANG COTTON HOTEL STYLE SHEETS. THIS UNIT ALSO HAS A FULLY RESTOCKED COOKS KITCHEN, GRANITE COUNTERTOPS, ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 300 feet to Siesta Beach

$723

avg/night

$723
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

Featured review

"Great property on the sand."

We had a great week despite the heat of summer. This house although dated was clean, cool and comfortable. It was a two minute walk through the back yard to the sand. We had a few minor house keeping ...

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.7 miles to Siesta Key Beach

$764

avg/night

$764
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, fire pit, and fishing ...

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Property Type

Siesta Key House

Featured review

"Best vacation ever!"

If I could give 100 stars I would! Danielle and Jeb have thought of everything to make a great vacation spot and they are so easy and fun to work with. Beautiful decor! So kid friendly, great beds, great ...

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Siesta Key Vacation Rentals