5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING
For those seeking a truly amazing vacation experience! Come and experience the very BEST in hospitality on Siesta Key. Our property is a beautiful spacious retreat in the best location.
Our average length of stay requirements vary between 4-14 nights, and 7 nights during our high season. If the travel dates you are looking for do not meet our advertised minimum requirements, please contact me directly and I will see if we can accommodate your request.
Stunning and spacious 555 Beach Road. The home offers more than 3600 square feet of sophistication inside and a large private back yard oasis with resort pool area. Equally important - a truly amazing location 90 feet to beach access 10. Unlike other vacation rentals, you Avoid long walks and crowds - we are directly across from a more private section of the number beach in the entire US. Our guests walk back and forth throughout the day to Siesta Key Beach, the # 1 Beach in the US - and walk to Siesta Village and its great restaurants for meals.
We work hard to make this the perfect vacation home and check to make sure you are taken care of while you are here. Our Brand new fully stocked chef's kitchen with quartz countertops & white lacquer cabinetry makes for great entertain. The house comes with beach caddies, beach towels, beach umbrellas, beach toys, and more.
Please note that our vacation home consists of two units under one roof offering more privacy - with the ease to move back and forth. This listing is for both units, 6 bedrooms, 4.5 baths, plus two outdoor heated showers. The two units together create one of the most spacious 6-bedroom 5-baths on Siesta Key! Our home sleeps 14 very comfortably. If you need more flexibility with sleeping arrangements we have high-end air mattresses in each unit.
The two units under one roof work well together as the front doors to each unit face each other, so it's convenient to move back and forth. Inside the spacious front unit, enjoy wonderful light as you walk into an expansive living room and great open kitchen (with bar and a separate dining area), making this a perfect spot for entertaining. Continue the party - or simply relax and take in the sun - wall to wall sliding glass opens onto the outdoor balcony with dining area, relaxing sofa, and partial water views. Upstairs are 3 bedrooms, 2.5 baths, with balcony and partial water views. The Master bedroom has a King bed set, outdoor balcony, large walk-in closet, and ensuite bath with 2 sinks, jacuzzi tub, separate shower, and toilet. The 2nd bedroom has two queen beds, shared balcony, large walk-in closet and the third bedroom has two twin beds. The 2nd large bathroom upstairs has separate shower and separate tub. The main living level offers a 3rd - 1/2 bath, a separate washer/dryer room off the kitchen. The property also two showers outside.
The beautifully furnished 3 bedroom 2 bath pool facing unit is spacious with a dining, kitchen and living area. The living room has large sliding glass doors opening up to a balcony and dining area that overlooks the backyard, palm trees, and our stunning resort pool. The bedrooms are upstairs. Two bedrooms have king beds and the third bedroom has a queen. We provide high end linens, beach towels, beach caddies, umbrellas, beach toys, and more.
NEW RESORT POOL AREA & PRIVATE BACKYARD to play in. The lush and tropical landscaped backyard offers 3 dining areas, BBQ grill, and a new gorgeous 25-foot heated pool. Home fully equipped with new furnishings and all the upscale amenities, fully loaded for discerning travelers. Additional New features throughout: new Air Conditioning and new a/c duct work (great for anyone with allergies.)
We live on Siesta Key to make sure your stay is wonderful. It's worth noting: beach access is right across the street from our home - this a big plus. Some homes, even though they are on Beach Road are not close to beach access.
Our address is 555 Beach Road, right across from the beach and 1/2 mile walk to Siesta Village restaurants. If you only need 3 bedrooms, each unit can also be rented separately (see property 977754.) The backyard deck (exclusive to the pool-facing unit) has an outdoor dining table overlooking the pool and backyard. The front-facing unit has a balcony with a dining table, lounge furniture, and partial views of the beach.
The property is located directly across the street from Siesta Key Beach, ranked the number one beach in the entire US.
Additional notes: Two bedrooms in the front unit offer large walk-in closets. Bathrooms are large and spacious. Please see pictures for more details. We offer high speed internet and have new high definition flat screens throughout. Please note: our published rates are subject to change. While we offer fewer than 7 day rentals during the Fall and some off season weeks, we require minimum 7 day stays during most holidays and during our busy seasons. Please email if you have any questions.
To understand more about our commitment to you and hospitality, please read our reviews.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Bright and Beachy 5 Bedroom/3 Bath House. Short Walk to Beach & SK Village!
Siesta Key Village
Bright and Beachy 5 Bedroom/3 Bath House. Short Walk to Beach & SK Village!
A copy of driver’s license will be required after booking.
Important information
You need to know
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, a first aid kit and a deadlock
About the area
Siesta Key
Located in Siesta Key, this holiday home is in the city centre and on the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Mote Marine Laboratory & Aquarium and St. Boniface Episcopal Church Labyrinth are also worth visiting. Enjoy the area's slopes with skiing, and don't miss out on the ice skating.
Siesta Key Beach Playground - 13 min walk - 1.2 km
St. Boniface Episcopal Church Labyrinth - 19 min walk - 1.7 km
Crescent Beach - 5 min drive - 4.4 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 24 min drive
Restaurants
Siesta Beach Pavilion - 9 min walk
Siesta Key Snack Bar - 9 min walk
Circle K - 15 min walk
Gilligan's Island Bar & Grill - 10 min walk
Sun Garden Cafe - 13 min walk
Frequently asked questions
Does 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING?
As of 7 May, 2026, prices found for a 1-night stay for 2 adults at 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING on 22 May, 2026 start from S$2,715, 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 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING pet-friendly?
No, pets are not allowed at this property.
How much is parking at 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING?
On-site parking is available at the property.
What time is check-in at 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING?
Check-in begins at 4:00 PM.
What time is check-out at 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING?
Checkout is at 9:30 AM.
Where is 5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING located?
Located in Siesta Key, this beachfront holiday home is in the city centre and 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).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This house was amazing. 12 family members had their own space and a huge kitchen, dining and living room to all gather and eat, play games and just chill. So close to the beach with all the beach chairs, towels, toys etc you could possibly need. David was very gracious and helpful. His suggestion for catering was top notch. I highly recommend 555 Beech Rd Siesta Key for your family memories vacation!
Sherry F.
Stayed 7 nights in Apr 2026
Response from VrboOwner on 5 May, 2026
Dear Sherry!
Thank you so much for the 5 star review! You were amazing to work with and it was wonderful for me to meet you after communicating throughout the year. Thanks also for commenting about our huge dining and living room and all of our beach chairs and amenities. Your family was amazing and we would love to see you back one day soon!
Warm regards to you and your family,
David
Dear Shannon,
Thanks for the awesome review and being wonderful guests. If I can ever be of service on Siesta Key, please let me know.
Kind regards,
David
Amazing stay with family! David was a fantastic host and gave us tips for 4th of a July weekend. This house has EVERYTHING you need. It was perfect!!
Raquel A.
Stayed 4 nights in Jul 2025
Response from VrboOwner on 23 Mar, 2026
Raquel,
I'm so glad you had an awesome July 4th week here and thank you for being great guests! If I can ever be of service on Siesta Key, please let me know.
Kind regards,
David
This is a beautiful property! I love the layout ! If two families are traveling together you have two separate spaces but a large gathering place in one of the spaces! The beach is an easy walk from the property! The owner has buggies and chairs , everything needed for a fun day at the beach! The owner was very hospitable and helpful! We were very pleased !
CATHY P.
Stayed 7 nights in Oct 2025
Response from VrboOwner on 23 Mar, 2026
Dear Cathy, A belated thank you for your detailed 5 star review and mentioning our home's wonderful layout and large gathering space for families. Thank you again for staying with us andI hope to see you back one day soon.
Warm regards,
David
Very close to the beach, a short walk to the village, and plenty of common space for family gathering.
Andrea G.
Stayed 5 nights in Jan 2025
Response from VrboOwner on 2 May, 2025
Andrea, Thank you for the awesome review on "GREAT LOCATION". It was a pleasure having you and your nice family stay with us! Thanks for pointing out how spacious our home is, too. I hope to see you one day soon.
Kind regards,
David
Dear Brad,
Thank you for highly recommending us and the 5 star review!
I hope your coaching schedule works out so that we get to see you and your family again next year.
Warm regards,
David
This property was perfect for our family gathering. Enough space to sit and talk and the pool was wonderful. Plenty of beach chairs, toys, towels and beach buggies to enjoy a day at the beach.
Marjorie B.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 25 Jun, 2025
Dear Marjorie,
Thank you for the 5 stars!!!!! It was a true pleasure to host your family and I’m so glad to hear everyone approved. Thanks for commenting on our wonderful pool - it is always satisfying to know that guests enjoy spending quality time in our backyard pool area. From Siesta Key Beach to Siesta Village, our pool, to great meals, you seemed to enjoy a full Siesta Key experience.
If you ever need anything on Siesta Key, please give me a call. We would love to have you back.
Kind regards,
David
This is a beautifully furnished and managed property. We stayed for a week with 7 adults and 4 small children, and we all had a great time.
Verified traveller
Stayed 7 nights in Mar 2025
Response from VrboOwner on 2 May, 2025
Dear Steve, Thanks so much for the 5 Star Review and trusting your vacation with us! It was a pleasure having you and your nice family stay at 555. Thanks also for commenting on our beautiful furnishings. I have an interior design person that will appreciate your feedback. Please let me know if you ever need anything on Siesta Key.
Kind regards,
David
David was a great host, and the house was everything we expected it to be! We rented it for a family vacation with our kids and grandkids and the 6 bedrooms, and 4.5 baths allowed privacy while the large great room and kitchen were perfect for meals and family time. The house well stocked with plenty of linens and beach towels and an abundance of beach toys, chairs and umbrellas, plus two wagons to haul everything on the short two-minute walk to one of the nicest beaches we've experienced. The pool and back patio were also well used as we grilled dinner a few nights during our stay. Our host stopped by to say hi and checked in via text a couple of times to make sure everything was okay. We had one minor maintenance issue, and he had it taken care of that same day. David also provided a bottle of his favorite wine for us to enjoy. We were there during spring break, so we didn't go to the Village much with 6 smaller children and the long waits at restaurants, although it looks worthy of exploration on a future visit. We did rent Kayaks at Turtle Beach from Sarasota Kayak Rentals and had an amazing day, seeing dolphins and sea shelling at the Midnight Pass. We also ventured up to Lido Beach and spent a fun day on the sandbar.If you are looking for a great location and a great house for a family vacation, this is the one and David is your host!
Tom C.
Stayed 6 nights in Mar 2026
Response from VrboOwner on 17 Apr, 2026
Dear Tom,
Thank you for taking the time to write such a heartfelt and thoughtful review. It was truly my pleasure to host you and your family.
We put great care into creating a memorable Siesta Key beach experience, so it’s especially rewarding to know the home provided the perfect setting for meaningful family time—whether gathering in the great room, enjoying relaxed evenings by the pool, or spending time on the beach just steps away. And well done making time for kayaking at Turtle Beach—that sounds like a fantastic day.
It’s wonderful to hear your stay reflected the kind of effortless, memorable experience that makes Siesta Key so special. I’m sincerely grateful for your kind words.
We would be delighted to welcome you and your family back anytime. It would be a privilege to host you again.
Warm regards,
David
We came down to celebrate our daughter's 16th birthday with friends and family. All of us had a wonderful time. David was great about all aspects of the rental. Thank you!
We had a fantastic stay with family! Great location close to beach access, trolley stop, and village
Perfect house for our big family vacation. The back yard and pool area was especially nice as well as the front balcony.
Sarah B.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 28 Jun, 2022
Hi Sarah! Thank you for the 5 star review and pointing out our great location on Siesta Key Beach. I'm so glad our home was a perfect fit for your large family. It was a pleasure to meet all of you and I hope to see you back on Siesta Key soon. Warm regards, David
Working at 29 Palms and this house was perfect for what my coworkers and I needed for the week.
Nick H.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 20 Feb, 2024
Thanks so much for the 5 stars! I'm so glad our property was perfect for you. If you ever need anything on the Key, we would love to host you. Best regards, David
This place was perfect for a family vacation! The beach access was right across the street and it was easy to walk to downtown. The owner provided plenty of wagons, umbrellas, and plenty of towels for the beach. The heated pool was amazing, and the grilling area in the back was super cozy. House was comfortable and lots of room for everyone to have their own space.
Gina B.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 2 May, 2025
Hi Gina, Thanks so much for mentioning our Amazing Location and that the property is perfect for a family vacation! I'm so glad that your family had a great time. I'm sure the kiddos will treasure their memories on Siesta Key with you. I hope to see you back again one day soon. Thanks again for staying with us! Kind regards, David.
Perfect set-up for our family vacation. Children with kids stayed in one unit, while Wife and I and other Children without kids stayed in the other unit. Main unit is perfect for family meals, conversations, relaxation together. Pool was a very nice daily break and the village and beach were closer than advertised!
Exactly what we expected. Plenty of room for 5 couples, spacious and sunny great room/kitchen area, nice pool area in back. Would definitely stay here again.
Todd B.
Stayed 5 nights in Jan 2025
Response from VrboOwner on 2 May, 2025
Dear Todd,
Thank you for the 5 STARS and pointing out our nice pool area and large sunny main room. We are proud to boast that our kitchen, living and dining area is unique and a rare find on Siesta Key because it's so spacious and designed with family gatherings in mind. We look forward to having you back! Kind regards, David
This property is exactly as advertised and better. Location is phenomenal. We walked everywhere. The kitchen was well stocked and the furniture very comfortable. The pool area is amazing.
Justine F.
Stayed 4 nights in Feb 2025
Response from VrboOwner on 2 May, 2025
Dear Justine,
Thanks for this awesome review! We are so pleased that you had an amazing stay with us. Thank you for pointing out the phenomenal location (right across from the beach) and that you can walk everywhere, including Siesta Key Village. It can be difficult for first time visitors to Siesta Key to determine what the "best location" is. So, thank you.
It was a true pleasure to work with you and thanks for taking great care of our home! We look forward to having you back at 555 Beach soon!
Warm regards, David
We’ve stayed in Siesta key several times and this place was incredible. The beds were all extremely comfortable. The location is perfect, just steps from the beach and the town. The pool and patios were also terrific too. This place is worth every penny!
Mark B.
Stayed 4 nights in Oct 2021
Response from VrboOwner on 14 Oct, 2021
Hi Mark,
Thanks for this amazing review! I appreciate the details about our property and your incredible experience here.
So glad to hear you're coming back, too. Thanks again for your business!
Kind regards,
David
This property is amazing. So clean, plenty of space for everyone, great pool area and an abundant amount of beach toys and supplies. The kitchen is stocked with everything you need to prepare and store meals. Plenty of beach and house towels. David, the owner, has gone above and beyond having the property ready for your group to have a fabulous time. Would definitely recommend!!
SUNRISEx x.
Stayed 6 nights in Jun 2025
Response from VrboOwner on 25 Jun, 2025
Dear Melodi,
Thank you for the high praise! We're thrilled to hear that you had a fabulouse time — and especially honored to know that this was one of your best vacations! Thank you again for staying with us and I hope to welcome you back for another unforgettable visit soon!
Warm regards,
David
We had 12 people in this location with plenty of room. The host was very attentive and quick to respond to text messages. The house itself is beautiful. The host has everything you need to make your stay perfect. The location is a very short walk to the beach and the village. I look forward to another vacation in this location in the future
joanne p.
Stayed 7 nights in May 2025
Response from VrboOwner on 25 Jun, 2025
Dear Joanne,
Thank you for this wonderful 5 star review! I'm so happy to hear that 555 Beach was beautiful! And spacious and the perfect fit for you. I would love to welcome all of you back someday soon! Thanks again for staying with us.
Kind regards,
David
A property manager dedicated to making sure a group of old friends had a delightful time, we can only say thank you for making our stay so comfortable. Hope to visit another time and most assuredly would highly recommend.
We really enjoyed our stay. The house was just like the pictures. The location was perfect. Lots of beach chairs to use, nice pool. Kitchens stocked.
Tracy L.
Stayed 7 nights in Jan 2021
Response from VrboOwner on 29 Jan, 2021
Hi Tracy, It was such a pleasure having you and your nice family stay with us! Thanks so much for commenting on our brand new fully stocked chef's kitchen, our location, and beach chairs. I hope to see you again soon.
Kind regards,
David
Great host who gave good recommendations for activities and restaurants. Location is great for a relatively quiet part of a beautiful beach and easy walking to a choice of restaurants. Lovely garden which is shaded for much of the day.
Clare B.
Stayed 7 nights in Feb 2023
Response from VrboOwner on 20 Mar, 2023
Dear Clare,
It was lovely to meet you and your family. Thank you for the 5 stars and pointing out our great location and lovely garden and pool area. If I can ever be of assistance on Siesta Key, please call me directly on my cell. Kind regards, David
About the host
Hosted by David
I have a diverse background that includes a decade working in luxury travel, hotels, and a decade in journalism. I'm also an alumnus of Cornell's Hotel School, the top hospitality school in the world. Needless to say, we live and breathe hospitality and work hard to make sure your stay is wonderful. My wife and I live on the Key and raise our family here. We look forward to meeting you!
Why they chose this property
BEST BEACH LOCATION and LAID BACK SOPHISTICATION. This is one of the nicest homes on Siesta Key Beach and our location separates this property from the rest. We are on Beach Road - 90 steps from Beach access 10, a more private portion of the best beach in the world! Walk back and forth to the beach throughout the day. This is also a large spacious duplex home, allowing you to spread out and enjoy yourselves. Both spaces offer spacious and open living areas that are great for entertaining (very hard to find on Siesta Key - this is a truly exceptional aspect of this property - the living room is spacious!). Indoor and outdoor sophistication, with a brand new heated resort pool and private lush backyard. Backyard has 3 dining areas and BBQ, too! All new High Def Flat screen smart 4K TVs.
What makes this property unique
Walk back and forth to the beach all day! Walk the beach right into the village. Beautiful New Backyard includes brand new 25- foot heated pool surrounded by paver bricks and 3 dining tables/BBQ and beautifully landscaped backyard. Home comes with beach chairs, beach towels, and don't hesitate to ask for a chef. We can put you in touch with a great chef if needed!