Siesta Key Island Rentals

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Photo gallery for Siesta Key Island Rentals

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.
A spacious living area with a dining table, white chairs, a chandelier, and a large window overlooking a pool.
A spacious living room with a fireplace, a dining area, and a view of the outdoors.
A modern living room with a beige sofa, a coffee table, and a chandelier. There is a kitchen area in the background with a dining table and chairs.
A spacious living area with two grey sofas, a wooden coffee table, and a view of a swimming pool through large glass doors.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Siesta Key Beach

Popular amenities

  • Free Wi-Fi
  • Washer/dryer
  • Self-parking included
  • Kitchen
  • Non-smoking

Explore the area

View map
515 Beach Rd, Siesta Key, FL, 34242
  • Place, Siesta Key Beach
    ‪1 min walk‬
  • Place, Siesta Key Farmers Market
    ‪9 min walk‬
  • Place, Siesta Key Beach Playground
    ‪15 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Choose your unit

View all photos for 447 Avenida De Mayo, Siesta Key, FL W/Pool

A covered outdoor swimming pool with a patio area, including seating and a table.

447 Avenida De Mayo, Siesta Key, FL W/Pool

  • Water view
  • 139 sq m
  • 3 bedrooms
  • Sleeps 8
  • 2 King Beds and 2 Double Beds

View all photos for 5405 Plaza De Las Palmas, Siesta Key, FL W/Pool

A bedroom with a bed, nightstands, a ceiling fan, and a window with blinds.

5405 Plaza De Las Palmas, Siesta Key, FL W/Pool

  • 130 sq m
  • 3 bedrooms
  • Sleeps 7
  • 1 King Bed, 2 Single Beds and 1 Queen Bed

View all photos for 516 Canal Rd, Siesta Key, FL W/Pool

A two-story house with a swimming pool, outdoor furniture, and a wooden deck.

516 Canal Rd, Siesta Key, FL W/Pool

  • 51 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for 518 Canal Rd, Siesta Key, FL W/Pool

A two-story house with a swimming pool, outdoor furniture, and a wooden deck.

518 Canal Rd, Siesta Key, FL W/Pool

  • 51 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for 5405 Plaza De Las Palmas, Siesta Key, FL W/jacuzzi

A bedroom with a large bed, a bedside table with a lamp, a window with blinds, a ceiling fan, and a sign that says "RELAX".

5405 Plaza De Las Palmas, Siesta Key, FL W/jacuzzi

  • Garden view
  • 37 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for 5405 Plaza De Las Palmas, Siesta Key, FL W/Pool

A bedroom with a large bed, a bedside table with a lamp, a window with blinds, a ceiling fan, and a sign that says "RELAX".

5405 Plaza De Las Palmas, Siesta Key, FL W/Pool

  • 167 sq m
  • 4 bedrooms
  • Sleeps 10
  • 2 King Beds, 1 Queen Bed, 2 Single Beds and 1 Double Sofa Bed

View all photos for 449 Canal Rd, Siesta Key, FL W/Pool

A pool area with lounge chairs and a small table, surrounded by greenery and a building with a balcony.

449 Canal Rd, Siesta Key, FL W/Pool

  • Canal view
  • 240 sq m
  • 3 bedrooms
  • Sleeps 8
  • 2 King Beds and 2 Queen Beds

View all photos for 5230 Avenida Navarra, Siesta Key, FL W/Pool

A swimming pool surrounded by blue chairs and a yellow building.

5230 Avenida Navarra, Siesta Key, FL W/Pool

  • 121 sq m
  • 3 bedrooms
  • Sleeps 6
  • 2 King Beds and 1 Queen Bed

View all photos for 322 Calle Miramar, Siesta Key, FL W/pool

A swimming pool with a brick border, surrounded by palm trees and a covered patio area with outdoor furniture.

322 Calle Miramar, Siesta Key, FL W/pool

  • Garden view
  • 120 sq m
  • 3 bedrooms
  • Sleeps 6
  • 3 King Beds

View all photos for 330 Avenida De Paradisio, Siesta Key, FL W/Pool

A swimming pool with a covered area, surrounded by a brick patio and lush greenery.

330 Avenida De Paradisio, Siesta Key, FL W/Pool

  • 218 sq m
  • 3 bedrooms
  • Sleeps 8
  • 2 King Beds, 1 Queen Bed and 1 Queen Murphy Bed

View all photos for 5224 Avenida Navarra, Siesta Key, FL W/Shared Pool

A bedroom with a bed, a ceiling fan, a window, a dresser, and a mirror.

5224 Avenida Navarra, Siesta Key, FL W/Shared Pool

  • 115 sq m
  • 2 bedrooms
  • Sleeps 8
  • 1 King Bed, 2 Queen Bunk Beds and 2 Single Beds

View all photos for 5240 Avenida Navarra, Siesta Key, FL W/Shared Pool

A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a window with a view of the outside.

5240 Avenida Navarra, Siesta Key, FL W/Shared Pool

  • 111 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 2 Single Beds and 1 Double Sofa Bed

View all photos for 711 Beach Rd, Siesta Key, FL No Pool

A bedroom with a large bed, a nightstand, a chandelier, a window with blinds, and a decorative wall piece.

711 Beach Rd, Siesta Key, FL No Pool

  • Partial ocean view
  • 51 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed

View all photos for 511 Avenida De Mayo, Siesta Key, FL W/Pool

A swimming pool with a lifeguard chair, a shaded area, and a white pergola in the background.

511 Avenida De Mayo, Siesta Key, FL W/Pool

  • Canal view
  • 167 sq m
  • 3 bedrooms
  • Sleeps 8
  • 2 King Beds and 3 Single Beds

View all photos for 447 Canal Rd, Siesta Key, FL W/Pool

A residential property with a swimming pool, outdoor seating area, and a covered patio.

447 Canal Rd, Siesta Key, FL W/Pool

  • Water view
  • 232 sq m
  • 3 bedrooms
  • Sleeps 8
  • 1 King Bed, 1 Queen Bed, 2 Double Beds and 1 Single Bed

View all photos for 1228 Siesta Bayside Dr, Siesta Key, FL W/Shared Pool

A bedroom with two beds, a ceiling fan, a window with blinds, a painting, a nightstand with a lamp, and a door leading to another room.

1228 Siesta Bayside Dr, Siesta Key, FL W/Shared Pool

  • Lagoon view
  • 119 sq m
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Single Bed

View all photos for 5365 Calle Florida, Siesta Key, FL W/Pool

A bedroom with a bed, ceiling fan, bedside lamps, a nightstand, and a dresser.

5365 Calle Florida, Siesta Key, FL W/Pool

  • 4 bedrooms
  • Sleeps 10
  • 2 King Beds, 1 Queen Bed and 3 Single Beds

View all photos for 5204 Avenida De Cortez, Siesta Key, FL 34242 W/Pool

A bedroom with two beds, a ceiling fan, a TV mounted on the wall, and a floor lamp.

5204 Avenida De Cortez, Siesta Key, FL 34242 W/Pool

  • 139 sq m
  • 3 bedrooms
  • Sleeps 8
  • 2 King Beds and 2 Queen Beds

Similar properties

Living area
2 bedroom 2 bathroom condominium is located on the Gulf side of our property.
Sarasota
  • Pool
  • Kitchen
  • Free Wi-Fi
  • Laundry room
9.6 out of 10, Exceptional, 58 reviews
The price is AU$1,136
AU$379 per night
includes taxes & fees
29 Nov - 2 Dec
2 bedroom 2 bathroom condominium is located on the Gulf side of our property.

Frequently asked questions

Is Siesta Key Island Rentals pet-friendly?

No, pets are not allowed at this property.

How much is parking at Siesta Key Island Rentals?

Self-parking is free at this property.

What time is check-in at Siesta Key Island Rentals?

Check-in start time: 4:00 PM; check-in end time: anytime.

What time is check-out at Siesta Key Island Rentals?

Checkout is at 10:00 AM.

Where is Siesta Key Island Rentals located?

Situated in Siesta Key, this holiday home is within 1 mi (2 km) of Siesta Key Farmers Market and Siesta Key Beach. Siesta Key Beach Playground and St. Boniface Episcopal Church Labyrinth are also within 1 mile (2 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on selected room rates because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

Siesta Key Island Rentals Reviews

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 69 out of 84 reviews
Rating 8 - Good. 9 out of 84 reviews
Rating 6 - Okay. 2 out of 84 reviews
Rating 4 - Poor. 3 out of 84 reviews
Rating 2 - Terrible. 1 out of 84 reviews

9.6/10

Cleanliness

9.0/10

Amenities

9.4/10

Property conditions & facilities

9.8/10

Check-in

9.6/10

Communication

9.2/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great location, very clean and spacious.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Good job
Stayed 3 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
The property inside was fine and spacious, we liked the coziness inside but was a bit outdated. The main entrance and screened patio and curb appeal overall shaggy not too invited in comparison with the new modern construction around. The one bathroom was ok, great shower but the vanity very very small and outdated. Loved the kitchen.
Stayed 6 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach.
Stayed 2 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities, communication
Wonderful stay,Great owners,Fun times
Stayed 6 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Very nice place, we loved it. Great location.
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Communication, listing accuracy
We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars!
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
I would highly recommend 447 Canal Street. It was beautiful, clean, updated and comfortable. There were a lot of stairs so consider that when planning your trip. Love that it has its own pool. All the dishes and pots/pans/utensils were new and desirable for use. We will be returning!
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great vacation stay
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We loved the property. Access to multiple hot tubs, laundry, individual units. Loved the beach chairs, umbrella, cart and cooler for our stay. We didn’t even need shoes-walked right across the street to the beach. Everything we needed and more.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Awesome
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Clean and everything we needed was there! Great location! Walking distance to great restaurants and shops. Very accommodating!
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, room comfort, communication
Enjoyed our stay and relaxing
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Location, location, location! Walked down the street everyday for restaurants and shopping. The house has everything you need and a private yard on the water. Felt like we were at home.
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, room comfort, communication
Great place! Walk to beach!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, room comfort, communication

Really amazing stay!

Amazing place! We loved it. Wish we could have stayed longer!
Stayed 3 nights in May 2025
Verified review

8/10 Good

Liked: Cleanliness, communication
Disliked: Amenities, property conditions & facilities
Gabe was very helpful to answer any questions. Steve was also very helpful.
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, room comfort, communication
This was a very comfortable stay with convenience to the beach, dining and shopping. Will definitely consider this location again when we travel to the area.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Quiet neighborhood, clean and well maintained property, responsive management.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Clean and close to beach
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities
Beautifully updated and has everything we needed to enjoy time in the condo and at the beach. Quiet, too, for being so close to the village.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
We had such a great stay! We arrived, parked the car and everything was within walking distance. Made a very relaxing stay!
Stayed 2 nights in Apr 2024

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