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Luxury Vacation Rentals in Siesta Key

(15 rentals)
New
Siesta Key House
Sleeps 16, 4 bedrooms, 3 bathrooms
1 review

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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$1,278
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

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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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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$800
avg per night
Siesta Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
14 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

"What a fantastic home and location?!!"

We just spent a full week at 5589 Cape Letye and had a wonderful experience. We had a total of 6 adults and 4 teenagers and we had more than enough space in the home. The home is gorgeous both inside and...

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$906
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

About this property

Your private Siesta Beach escape! Walk or bike to sand, unwind in the heated saltwater pool or Sauna and bring your furry friends along!Key Differentiators & AmenitiesSought-after Siesta Key Family & Pet friendly location—easy access to the beach, village, shops, restaurants, coffee...

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Featured review

"Paradise"

The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience...

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$807
avg per night
New
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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$923
avg per night

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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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$816
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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$793
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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$802
avg per night
Siesta Key Villa
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car...

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$718
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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$754
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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$775
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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$904
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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$798
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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$827
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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$764
avg per night
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