Entire home

New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky

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Poolside Escape
Close to Beach
Private Pool and Spa
Outdoor Living Area
Outdoor Dining Area

Reviews

9.8 out of 10
Exceptional
4 bedrooms4+ bathroomsSleeps 8

Popular amenities

  • Private pool
  • Spa pool on site
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine

Explore the area

View map
Anna Maria, FL
  • Place, Bradenton Beach
    ‪1 min walk‬
  • Place, Island Players
    ‪2 min walk‬
  • Place, Bean Point Beach
    ‪14 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪34 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Bunk Beds

4 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

Kitchen
Balcony

About this property

New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky

Siena Sky by Anna Maria Island Accommodations

Welcome to Siena Sky, a four-bedroom, four-bath luxury vacation home just steps from the beach. This stunning island getaway combines modern elegance with relaxed coastal comfort, featuring a rooftop deck with Gulf views, a heated pool and spa, and a prime location within walking distance of Pine Avenue, Bean Point, and the island’s best shops and restaurants. Perfect for families and groups, Siena Sky delivers the ultimate Anna Maria Island vacation experience.

Highlights
• 1-minute walk to Anna Maria City Beach
• 4 Bedrooms / 4 Bathrooms
• 3 King beds, 2 Twin-over-Twin bunk beds
• Rooftop deck with Gulf views
• Brand new construction
• Heated pool with spa
• Elevator access
• Covered patio with seating and BBQ grill
• Pet-friendly with approval and fee
• 4 parking spaces

Wake up to breathtaking views from the rooftop deck, spend sunny afternoons splashing in the pool and relaxing in the spa, and gather for dinners by the outdoor grill and covered patio. Siena Sky makes vacation living effortless, with upscale amenities like an elevator, washer and dryer, and upgraded linens to ensure every stay is comfortable and convenient.

The second floor living area is bright and inviting, featuring plush seating, TV, and sliding doors that open to the balcony for seamless indoor-outdoor living. The chef’s kitchen is a highlight with quartz countertops, custom cabinetry, and appliances, while the dining area offers elegant seating for eight. Whether you’re cooking a family feast or enjoying takeout from a nearby restaurant, this open concept space is perfect for gathering together.

Each of the four bedrooms is designed as a private retreat, complete with ensuite bathrooms, TVs, and plenty of storage. The primary bedroom boasts a king bed and a spa-inspired bathroom with a standalone tub and walk-in shower, plus balcony access for morning breezes. Two additional king bedrooms provide comfort and style, while the fourth bedroom is perfect for kids with two twin-over-twin bunk beds. With four and a half bathrooms, everyone in your group will enjoy space and privacy.

Room Details
-Primary Bedroom, 3rd floor: King bed, ensuite bathroom with tub and walk-in shower
-Second Bedroom, 2nd floor: King bed, ensuite bathroom
-Third Bedroom, 2nd floor: King bed, ensuite bathroom
-Fourth Bedroom, 3rd floor: Two Twin-over-Twin bunk beds, ensuite bathroom

Located just one minute from the beach and close to Anna Maria’s most popular spots, Siena Sky is perfectly positioned for exploring. Walk to boutique shopping and dining on Pine Avenue, take the trolley to Holmes Beach or Bradenton Beach, or spend the day kayaking, fishing, or booking a sunset cruise. Traveling with a larger group? Check out Costa Bella, Siena Sky’s neighboring home, also available for rent.

Siena Sky by Anna Maria Island Accommodations is the perfect blend of modern luxury and coastal charm. With a rooftop deck, private pool and spa, and unbeatable location near the Gulf, this home is designed to make your Anna Maria Island getaway unforgettable. Book your stay today and create lasting memories at Siena Sky!

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This home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. Please see our Anna Maria Island Accommodations Rental Policies for full details.

With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Anna Maria Island Accommodations Rental Policies for full details.

4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4096096vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Anna Maria

Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and ecotours.
Map
Anna Maria, FL

What's nearby

  • Bradenton Beach - 1 min walk - 0.2 km
  • Island Players - 2 min walk - 0.2 km
  • Anna Maria Island Museum and Historical Park - 6 min walk - 0.6 km
  • Bean Point Beach - 14 min walk - 1.2 km
  • Anna Maria City Pier - 14 min walk - 1.2 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 46 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬8 min drive
  • ‪The Ugly Grouper - ‬5 min drive
  • ‪The Sandbar Restaurant - ‬4 min walk
  • ‪The Waterfront Restaurant - ‬12 min walk
  • ‪Ginny's & Jane E's - ‬4 min walk

Frequently asked questions

Does New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky?

As of 9 May 2026, prices found for a 1-night stay for 2 adults at New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky on 6 Dec 2026 start from AU$1,344, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky pet-friendly?

Yes, pets are allowed at this property.

How much is parking at New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky?

On-site parking is available at the property.

What time is check-in at New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky?

Check-in begins at 4:00 PM.

What time is check-out at New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky?

Checkout is at 10:00 AM.

Where is New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky located?

Situated by the sea, this holiday home is within a 15-minute walk of Bradenton Beach and Bean Point Beach. Island Players and Palmetto Avenue Beach are just steps away.

Reviews

9.8

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. 5 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kathleen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home! Steps away from the beach and extremely accommodating.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 3 Feb 2026
Mahalo for the kind words, Kathleen! We’re so glad you loved the home and the easy beach access, it doesn’t get much better than that. Happy to hear our AMI Accommodations team could make your stay comfortable and stress-free. Come back and see us anytime!
Verified

10/10 Excellent

Wendy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was great.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 28 Jan 2026
Hi, Wendy, thank you so much for your kind review and staying with us at Siena Sky!
Verified

10/10 Excellent

Travis M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect. Great location, clear instructions, lots of support, and a beautiful, clean house.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 24 Dec 2025
Hi, Travis, thank you so much for the wonderful review and for choosing Anna Maria Island Accommodations! We’re thrilled to hear that everything was perfect, from the location and clear instructions to the support from our team. Knowing you enjoyed a beautiful, clean home means a lot to our local crew. We’d love to welcome you back to Siena Sky for another relaxing island stay soon!!!
Verified

10/10 Excellent

Leslie Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great modern house with a great pool and one block from the beach!
Stayed 5 nights in Aug 2025
Response from VrboOwner on 27 Aug 2025
Thank you for the great feedback, Leslie! We’re so glad you enjoyed the modern home, pool, and the easy walk to the beach. We’d love to welcome you back soon with Anna Maria Island Accommodations!
Verified

8/10 Good

Matt M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house & location. House was beautiful, well stocked & family enjoyed the pool, spa & short walk to beach. A couple things of note:1.) the motor for the elevator (or whatever sits above the stairs on the 3rd level) likely needs serviced. It would randomly make a loud noise for a few seconds at night. It took us 2 days to figure out what was making the noise, but would wake people up on the 2nd & 3rd floors.2.) the right side door on the refrigerator seemed loose and repeatedly would pop open even when just using the left side door. Door alarm kept going off.3.) there was an odd smell when first entering the house. Not sure if the renter before us was smoking, but this dissipated over time.
Stayed 4 nights in Jan 2026
Response from VrboOwner on 20 Jan 2026
Hi, Matt, thank you so much for sharing your experience at Anna Maria Island Accommodations | Siena Sky! We’re so happy to hear you loved the home, the location, and that your family enjoyed the pool, spa, and easy walk to the beach. That’s what island time is all about. We truly appreciate you noting the items you experienced during your stay. Our local team has shared this feedback with maintenance so the elevator motor noise and refrigerator door can be addressed. In the future, please do not hesitate to reach out to our local team during your stay so we can take care of any issues right away. We’re always happy to help!!
Verified

10/10 Excellent

Debra H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a girls trip. Loved the hot tub, pool, outdoor area plus nice bedrooms and kitchen. Close to beach, restaurants and a few shops. Also responsive host. Would stay there again.
Stayed 4 nights in Nov 2025
Response from VrboOwner on 21 Nov 2025
Hi, Debra, thank you for staying with us at Dockside Paradise. We’re thrilled to hear you loved everything about the home, inside and out. It’s such a peaceful spot for relaxing and soaking in island life. Our team truly appreciates your kind words and we’re so glad we could help make your stay easy and enjoyable. We hope to welcome you back soon with AMI Locals!!

About the host

Hosted by Anna Maria Island Accommodations

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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