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Siesta Key Vacation Rentals

(176 rentals)
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 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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$701
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Escape to this charming 3-bedroom house on Siesta Key, offering a private pool and a 2-car garage just a short distance from the beach. Enjoy amenities like a fully-equipped kitchen and a charcoal grill, which is perfect for family gatherings. With multiple TVs and high-speed internet, relaxation is guaranteed....

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$328
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Gorgeous Gulf front 2 bedroom/2 bath unit at Crystal Sands complex. Tile floors through kitchen, baths and living room. 3 TVs with washer/dryer in unit. Screened-in lanai off all rooms with direct access....

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$531
avg per night
Siesta Key House
Sleeps 9, 3 bedrooms, 2 bathrooms

Distance to beach: 0.7 miles to Siesta Key

Key Amenities

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

About this property

House of Siesta: our home by the coast. We’re opening our doors not to a regular rental but to our own home, created with love so guests can feel truly at home too. Just 0.7 miles from the #1 beach in the USA and minutes from Siesta Village, it’s spacious, welcoming, and perfect for two families...

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$380
avg per night

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Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come relax in this quiet bayside complex that is surrounded by whispering oaks. 2nd floor unit is a 2 bedroom/2 bath remodeled unit. Complex offers tennis courts, community pool and pier for fishing. Unit has tile in main traffic areas with carpet in bedrooms. Leather sofa, open kitchen wit granite countertops....

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$264
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool

About this property

The Condo Bay side water views; 2nd floorPrimary: King BedPrimary bath: tub/shower comboGuest: 2 twins/convert to KingGuest bath: tub/shower comboLiving Room: Sleeper Sofa

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Siesta Key Villa
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Completely remodeled, 1 bedroom/1 bath, 1st floor condo with private screened lanai with new pergo floors and new kitchen. Washer/dryer in unit located just one block from the shops and restaurants...

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$349
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tucked away in a quiet neighborhood in the heart of world-famous Siesta Key with a private pool. Discover your own slice of paradise in this beautifully updated 3-bedroom + den, 2-bath canal-front home. This stunning retreat offers modern elegance, luxurious furnishings and the ultimate blend of indoor...

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$517
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

3rd floor unit in the clubhouses located on the beachside of Palm Bay Club, which is steps from the beach. Custom cabinets, granite counters, stainless steel kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit. WIFI. Complex offers elevators, 2 pools (1 beachside, 1 bayside),...

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$409
avg per night
Siesta Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise on Siesta Key! This charming 2 bedroom/2 bath condo is just steps from the award-winning white sands of Siesta Key beach. Enclosed patio. Enjoy the refreshing pool and amenities like tennis and grilling. WIFI. No pets. Sleeps 4 (1 King, 2 Twins). 2-week minimum. Check in: 15:00 - 23:59 Check...

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$242
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury at its finest in this 1,600 sq. ft. Crescent condo complex. This unique 2 bedroom/2 bath 2nd floor unit opens directly to one of the two pools through an additional large outside dining patio with gas grill. Beautiful kitchen with open concept, washer/dryer in unit, bamboo floors throughout. High-def...

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$665
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/dryer, Private pool, decorated with a Island flare. Tile throughout with granite and stainless steel kitchen appliances. Beautiful setting pool and patio overlooking canal with boat dock. (Boat...

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$486
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

Discover the perfect balance of comfort, charm, and Florida sunshine in this beautiful home, ideally located just a short stroll from the world-famous Siesta Key Beach and the lively Siesta Village, filled with restaurants, cafés, and boutique shops. Bedrooms & Comfort Left side of the home: • One...

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Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit...

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$179
avg per night
Siesta Key Villa
Sleeps 3, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Enjoy spectacular views of the Gulf from all levels of this freshly remodeled, coastal contemporary townhouse featuring a master Bedroom with a den and luxurious bathrooms. The beach is just a block from Siesta Village offering restaurants, shopping and nightlife. This three-story unit features a convenient...

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$548
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 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. 4th floor unit is 1 bedroom, 1 bath on the corner with a washer/dryer. Complex offers community pool, tennis and community room. 1 assigned covered parking spot. Unit has 2 TVs, high-speed internet....

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$223
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Experience refined coastal living in this newly refurnished 2BR/2.5BA condo, where luxury meets relaxed island charm. Enjoy elegant décor, 800-thread-count linens, and a gourmet kitchen with granite and stainless steel. Sip coffee on the balcony with a Gulf breeze, unwind by two pools, or stroll...

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$609
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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$837
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Breathtaking Direct Oceanfront Condo – Wake up to panoramic views stretching the entire length of Siesta Key Beach in this elegantly appointed 9th-floor oceanfront retreat, perfectly located near the Stickney Point Bridge Village shops and restaurants and a marina. This residence offers designer...

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Featured review

"Great condo"

Location and condition and furnishings of condo are the best, the only suggestion we have (and it's not a deal breaker ) is a recliner or two would be great.

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$531
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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$817
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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$791
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Wake up to breathtaking views of the award-winning Siesta Key Beach from every room in this stunning, updated two-bedroom, two-bath condo. Designed for relaxation, this bright and airy retreat features an open floor plan, neutral tile, and an abundance of natural light. Step onto the screened-in lanai...

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$231
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Siesta Key Paradise! * available for winter/spring 2026* Your home away from home. Located in a prime spot on the quiet end of Siesta Key, this recently updated two-bedroom, two-bathroom is a great getaway.The condo is located at Mariners Inlet, which is an 8-unit complex located directly...

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$295
avg per night
Siesta Key House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Escape to your Siesta Key haven! This fully renovated 3-bedroom, 2-bath home, a mile from the world-famous beach, offers a perfect blend of comfort and convenience. Enjoy a modern open floor plan, a fully equipped kitchen, and a private pool in a fenced backyard. With comfortable sleeping arrangements...

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$302
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to the island and experience the #1 Beach in the USA! This updated end unit condo offers a spacious floor plan with a pool and is just two blocks from the award-winning white sand beaches. Enjoy convenient access to shopping and the shared laundry facilities. Assigned parking. No smoking. No pets....

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$220
avg per night
Full map
Map

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

FAQ

How many vacation rentals are there in/around Siesta Key?

There are 176 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to apartment rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $156 per night with an average price per night of $350.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 90 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 41 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!