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Luxury Vacation Rentals in Siesta Key

(16 rentals)
Siesta Key House
Sleeps 16, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Key Differentiators & Amenities•360 steps to Siesta Key Beach (#1 beach in the US) •Ample parking for RV, boat, and multiple vehicles •EV charging station onsite •Private saltwater pool (fenced backyard) •Pet-friendly: beds, crates, bowls, blankets, waste bags •4...

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$977
avg per night
Last Minute Deal
Siesta Key House
Sleeps 7, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.7 miles to Siesta Key Beach

Key Amenities

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

About this property

**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...

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Featured review

"Beautiful and comfy"

5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...

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$723
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
10 reviews

Key Amenities

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

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened...

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Featured review

"Fabulous vacation house"

My family, six adults and two young children, had an amazing week at this house on Siesta Key. We loved being able to walk out the door and be on the sand. We made sand castles and swam everyday. It doesn’t...

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$799
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away...

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Featured review

"Excellent"

The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar...

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$757
avg per night
Siesta Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
15 reviews

Distance to beach: 400 feet to Siesta Beach

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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Featured review

"Perfect home and location!!"

We had a fantastic stay! The location couldn't be better—it's incredibly close to the beach and village, making it easy to pop out for a beach stroll or dinner. The house itself offered plenty of space...

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$870
avg per night

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Siesta Key House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Gertrude's Village House Top location on the island with 3 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters...

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$709
avg per night
Siesta Key Villa
Sleeps 10, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry...

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$726
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our exquisite three-bedroom, two and a half-bath Siesta Key home, where the magic of the tropics meets unparalleled comfort and convenience! Imagine waking up to the vibrant spectacle of parrots gracefully flitting overhead, a delightful start to your vacation amidst our lush, tropical backyard...

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$807
avg per night
Siesta Key House
Sleeps 14, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Casa De Mayo — your private waterfront retreat in the heart of the island. Perfectly situated just a stroll from Siesta Village and the world-famous powder-soft sands of Siesta Beach, this stunning home offers the best of both worlds: vibrant island life and peaceful tropical seclusion....

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$1,000
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This lovely penthouse condo is in one of Siesta Key's luxurious complexes. The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this 3 bedroom/3 bath beachfront condominium with open-air balcony, living room, kitchen and...

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$921
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 2nd floor luxury beachfront condo is updated with designer furniture and furnishings. Fully restocked kitchen with granite countertops and stainless steel appliances. 3 bedroom/3 bath direct beach and pool views from either of the two balconies. Access to small workout room. Washer/Dryer in unit...

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$896
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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 STEEL APPLIANCES, AND NEW WOOD FLOORING IN ALL BEDROOMS. LARGE...

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$793
avg per night
Siesta Key Villa
Sleeps 15, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 3400 sq ft., 5 Bedroom 3.5 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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$968
avg per night
Siesta Key Estate
Sleeps 20, 6 bedrooms, 5 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key Beach

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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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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$804
avg per night
Siesta Key House
Sleeps 7, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 300 feet to Siesta Beach

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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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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$757
avg per night
Siesta Key Villa
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants...

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$763
avg per night
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