Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!
Mainsail by Siesta Key Luxury Rental Properties
Mainsail by Siesta Key Luxury Rental Properties is a breathtaking 4 bedroom, 3 and a half bath waterfront luxury home with a bonus room, private dock, and spectacular Intracoastal Waterway views. Nestled at the end of a quiet street and just a 10-minute walk to Crescent Beach, this upscale retreat offers a refined yet relaxed coastal lifestyle perfect for large families and groups. With a private pool, in-ground spa, multiple outdoor lounges, and seamless indoor and outdoor living. Mainsail sets the stage for an unforgettable Siesta Key luxury rental experience near South Siesta Key Village.
Highlights • 10-minute walk to Crescent Beach • 4 Bedrooms / 3.5 Bathrooms • 1 King, 4 Queens • Private dock (18 ft) • Private heated pool and in-ground spa • 2 kayaks included • Outdoor bar and outdoor kitchen • Covered outdoor dining and lounge areas • Wet bar and wine fridge • 5 parking spaces
Designed for waterfront relaxation, Mainsail features a private heated pool, a spa, and wide poolside terraces capturing panoramic waterway views. Enjoy evening cocktails at the outdoor bar, prepare meals in the covered outdoor kitchen, or gather for sunset dining on the balcony overlooking the Intracoastal. With two kayaks included, guests can explore the calm waterway right from the private dock. Every outdoor space is crafted for comfort, inviting you to unwind in a true tropical outdoor oasis.
Inside, Mainsail offers a bright and expansive open concept layout with designer inspired coastal interiors. Floor to ceiling windows frame sparkling water views throughout the living and dining areas, while the gourmet kitchen features high end appliances, generous counter space, and island seating ideal for group gatherings. The dining table seats nine comfortably for shared meals, and an additional wet bar with a wine fridge enhances the luxury entertaining experience. Multiple lounge areas, and beautiful hardwood floors throughout, create a warm, elevated atmosphere.
Retreat to the luxurious second-floor primary suite, complete with a king bed, ensuite bathroom, double vanity, walk-in shower, and walk-in closet, plus a convenient mini refrigerator. On the main floor, two guest suites offer queen beds and private ensuite bathrooms, one with a shower/tub combination and one with a walk-in shower. A fourth bedroom includes two queen beds, making it ideal for families or additional guests. The bonus room features a twin daybed, offering a space for relaxing or flexible use. All rooms are designed with calming coastal finishes to ensure a restful stay.
Room Details -Primary Bedroom (2nd floor): King bed, ensuite bathroom with double vanity + walk-in shower -Second Bedroom (1st floor): Queen bed, ensuite bathroom with shower/tub combo -Third Bedroom (1st floor): Queen bed, ensuite bathroom with walk-in shower -Fourth Bedroom (1st floor): Two Queen beds
This home includes a private dock, kayaks, outdoor bar, outdoor kitchen, multiple waterfront terraces, balcony seating, covered lounges, wet bar, and extensive space for up to five vehicles. Located near South Siesta Key Village, guests are close to shops, nightlife, restaurants, and beautiful Siesta Key Beach.
Mainsail by Siesta Key Luxury Rental Properties is a rare blend of waterfront elegance, luxury amenities, and prime island location. From its private dock and expansive outdoor spaces to refined interiors and incredible waterway views, this home offers the perfect setting for a memorable Siesta Key escape.
Book your stay at Mainsail today and experience the best of waterfront luxury on Siesta Key!
- This home is managed by Siesta Key Luxury Rental Properties.
This property does not allow pets of any kind.
This property has active video surveillance on the exterior public approach areas and the pool equipment.
5 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 see our Siesta Key Luxury Rental Properties Rental Policies for full details.
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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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
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
Siesta Key
Located in Siesta Key, this holiday home is on the waterfront. 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. Looking to enjoy an event or a game while in town? See what's happening at Ed Smith Stadium or Stardust Event Center. Looking to get your feet wet? Jet skiing, kayaking and parasailing adventures can be found near the property.
St. Boniface Episcopal Church Labyrinth - 2 min drive - 1.7 km
Siesta Key Beach Playground - 3 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 35 min drive
Restaurants
McDonald's - 3 min drive
Captain Curt's Crab & Oyster Bar - 14 min walk
Gecko’s - 3 min drive
Daiquiri Deck South Siesta Key - 14 min walk
The Sniki Tiki - 14 min walk
Frequently asked questions
Does Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!?
As of 9 May, 2026, prices found for a 1-night stay for 2 adults at Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach! on 11 Apr, 2027 start from S$1,611, 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 Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!?
On-site parking is available at the property.
What time is check-in at Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!?
Check-in begins at 4:00 PM.
What time is check-out at Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!?
Checkout is at 10:00 AM.
Where is Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach! located?
Situated on the waterfront, this holiday home is within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Siesta Key Marina and St. Boniface Episcopal Church Labyrinth are also within 1 mile (2 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Thank you so much for your 5-star review! We truly appreciate you taking the time to share your experience.
It was a pleasure hosting you, and we’re so glad you enjoyed your stay. Feedback like yours means a great deal to our team.
We would absolutely love to welcome you back anytime!
The house was amazing! Everything was super clean and is very close to Siesta Key beach. We loved it
The renting experience was easy and great.
Maribel H.
Stayed 5 nights in Sep 2022
Response from VrboOwner on 21 Sept, 2022
Maribel, thank you for taking the time to share your experience with us. We are happy to hear you enjoyed your stay, and we hope to host you again soon!
Beautiful Open Space with Dolphins Swimming by the Deck.
Amazing Location
Great Support
Andrew H.
Stayed 7 nights in Dec 2023
Response from VrboOwner on 12 Jan, 2024
Andrew, we appreciate your positive review and are thrilled to hear that you enjoyed the open space, dolphins by the deck, and the amazing location. Thank you for choosing our property, and we look forward to hosting you again.
Our family thoroughly enjoyed our stay in this beautiful home on the inter coastal waters. We loved being able to rent a boat, fish and kayak off of the dock. The walk to the beach was a little further than expected but doable. Amazing home for our group of 7 adults.
Jennifer w.
Stayed 5 nights in May 2025
Response from VrboOwner on 29 May, 2025
We are so happy to hear you enjoyed yourselves and appreciate you sharing your experience! We hope to host you again in the future!
Very nice property for family get together. Ages 10-84 did well!!!
ANdrea P.
Stayed 6 nights in Jul 2024
Response from VrboOwner on 2 Aug, 2024
We’re so glad to hear that everyone, from the youngest to the oldest, had a great time! It’s always our goal to provide a space that suits families perfectly! 🏡❤️
We had 7-9 guests (3 under seven years of age) and found the property wonderful and well supplied. We especially enjoyed the pool and kayaks. Plenty of room for family meals.
Ann S.
Stayed 5 nights in Oct 2023
Response from VrboOwner on 25 Oct, 2023
Thank you for taking the time to share your wonderful experience with us, Ann. We are glad you enjoyed your stay and hope to welcome you back soon!
The house is wonderul. Right on the bay and the amenities are all top of the line. I would rent it again.
lance D.
Stayed 5 nights in Sep 2021
Response from VrboOwner on 5 Oct, 2021
Dear Lance,
Thank you for reviewing your recent stay with us on beautiful Siesta Key! We are thrilled to know that you enjoyed our prestigious 'Mainsail' property and all of the amenities that we offer. It was our pleasure to host you and your group, you're welcome back anytime!
Sincerely,
Siesta Key Luxury Rental Properties
Jeff, it's fantastic to hear that you had a great experience during spring break! We're thrilled that you enjoyed your time with us. If there's anything specific that stood out to you or if you have any feedback to share, we'd love to hear it. We hope to welcome you back for more memorable experiences in the future!
We stayed 6 nights and everyone in my family of 10 were so happy and excited to stay in such a beautiful, gorgeous house right on the waterway and blocks from beach. Thank you management for quick responses.
Kevin W.
Stayed 6 nights in Sep 2024
Response from VrboOwner on 17 Sept, 2024
Thank you for your kind words! We’re thrilled to hear that your family of 10 enjoyed the beautiful house and its fantastic location on the waterway and near the beach. It’s great to know that everyone was happy and excited during your stay. We appreciate your recognition of our quick responses and are delighted we could contribute to your wonderful experience. We look forward to hosting you again in the future!
Wife, kids (8 and 6) and I had a blast staying at this property. The pool, hot tub, and dock access for my kids to fish were our favorites. Awesome sound system to listen to music while floating in the pool and great outdoor tv (huge) to watch March Madness. Massive kitchen with all the utensils needed. Highly recommend!
Justin D.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 4 Apr, 2024
Justin, thank you for sharing your experience! We're thrilled to hear that you and your family had a blast staying at the property. It sounds like you made the most of the amenities, with the pool, hot tub, and dock access being favorites for your kids to enjoy fishing. We're glad you appreciated the awesome sound system and the outdoor TV, which made your time by the pool even more enjoyable. It's great to hear that the kitchen had everything you needed, and we're delighted to receive your recommendation. We hope to welcome you all back for another fantastic stay in the future!
Very nice property. Great views of the waterway and relaxing outdoor area. Only gripe was there was no dishwasher detergent or any soap to clean the dishes. We’ve stayed at other VRBOs that had much more miscellaneous Kitchen and bathroom supplies.
Wayne H.
Stayed 7 nights in Feb 2023
Response from VrboOwner on 15 Feb, 2023
Wayne, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, outdoor area, and views. We also appreciate your feedback regarding supplies and will be sure to pass this on to our team. We hope to host you again sometime in the future!
Terrific house that is very well maintained. The kayaks, pool, and fishing dock were fantastic giving everyone lots to do. Tons of living space outdoors and in. Sitting on the balcony for our meals watching the boats and wildlife was so relaxing. Unfortunately, we had multiple issues with the bikes. I understand that the management company switched to a new bike vendor and were working out some issues. Overall a great experience and trip.
Ed T.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 28 Apr, 2025
We're beaming hearing about your amazing family vacation. Thanks for being legends about the bike situation, improvements are well underway! Come visit again soon.
This home was amazing and beautiful. Right on the water you couldn't ask for a better location.
This house is great and will make your stay with friends or family memorable. A great outdoor space with pool on the water. Has all of the things you need for a perfect get away. I stayed here with a group of girlfriends who travel every year for the last 15 years. Even though it was during covid we felt safe and the house was very clean. I would definately rent this home again and so should you!
Lisa V.
Stayed 3 nights in Dec 2020
Response from VrboOwner on 14 Jun, 2021
Lisa,
We're so glad that you chose Siesta Key for your girl's trip this year and that our beautiful Mainsail property was perfect for your group! During the pandemic, we instituted additional cleaning and sanitizing measures into our already rigorous 107 pt cleaning checklist. It's wonderful to know that you felt safe in our home during this uncertain time. We hope you'll come back and see us again, you're welcome anytime!
Kind regards,
Siesta Key Luxury Rental Properties
My family stayed at the house for 12 days. The view from the pool was beautiful and to watch the boats pass by. The house had bikes to use and a beach cart. Public beach was walkable. House was in perfect shape. We all enjoyed the kayaks and went fishing, fishing poles were also at the house.
Elzan O.
Stayed 9 nights in Dec 2022
Response from VrboOwner on 24 Jan, 2023
Elzan, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, pool, and views. We hope to host you again sometime in the future!
Absolutely beautiful vacation home! We had the most relaxing week during our stay. We’d have coffee every morning on the deck watching the boats and dolphins swim by. The house itself is stunning! Beautifully decorated, comfortable beds, large sofa that all 7 of us could relax on later in the evenings. The pool was amazing. Our kids swam from early morning until late in the evening. The staff were very prompt in their responses and very pleasant to deal with. I would definitely stay in this vacation home again and highly recommend for any family to stay here!
Meghan M.
Stayed 6 nights in May 2024
Response from VrboOwner on 20 May, 2024
Meghan, thank you for your glowing review! We're thrilled to hear that you had such a wonderful and relaxing week at our vacation home. It sounds like you made some fantastic memories.
We're delighted that the beds were comfortable and that the large sofa provided ample space for everyone to relax in the evenings. It's fantastic that the pool was such a hit with your kids and provided endless entertainment throughout the day.
We're also glad to hear that our staff were prompt and pleasant in their responses, ensuring that your stay was as smooth and enjoyable as possible.
Thank you for choosing to stay with us, and for recommending our vacation home to other families. We would be honored to welcome you back for another memorable stay in the future! If you have any special requests or preferences for your next visit, please let us know.
The property is as described (+); the home is beautiful and very clean. The location is perfect. Its a short walk to the beach, dining, stores. There's a shuttle stop at the end of the long driveway. Dolphins graced our presence every day. Beautiful views of sunrise and sunset. Easy check-in and out. The hot tub was nice (I was surprised how warm it was given how cold it has been)... The temp in the house was comfortable (again, surprised that the home is set and maintained at a cool temp given how big the place is). All around perfect stay!
Karen T.
Stayed 5 nights in Feb 2024
Response from VrboOwner on 4 Apr, 2024
Karen, thank you for your glowing review! We're thrilled to hear that you had a fantastic stay at our property and that everything met your expectations. It's great to know that you found the home beautiful, clean, and perfectly located. We're delighted you enjoyed the nearby amenities and the daily dolphin sightings. We appreciate your kind words about the check-in process and the comfort of the hot tub and house temperature. Thank you for choosing to stay with us, and we look forward to welcoming you back for another perfect stay in the future!
Beautiful and quiet. Hated to leave, it was so peaceful but great fun at same time. Pool, jacuzzi, arcade game for kids, games, kayaks, bikes- we used it all. Saw dolphins in Robert’s Bay on two occasions as well. Prop Mgmt was very responsive. Could use a Dyson for quick clean ups. Outside space is top notch.
Rod M.
Stayed 7 nights in Mar 2023
Response from VrboOwner on 18 May, 2023
Thank you for taking the time to share your wonderful experience with us, Rod. We are thrilled you enjoyed the home, pool, games, and communication with our team. We also appreciate your recommendation and will be sure to pass this on to our team. You were terrific guests, and we hope to welcome you all back again soon!
This house is amazing. The location can’t be beat. We had a great time. The pool/spa heater was giving us issues but the Property manager was always quick to respond and send someone to fix. Our only complaint is the bedrooms on the ground level have very hard beds. My kids ended up sleeping on the large comfy living room couch.
Kate E.
Stayed 5 nights in Nov 2020
Response from VrboOwner on 21 Dec, 2020
Kate,
Thank you so much for choosing our home for your Siesta Key vacation! We are so glad that your family enjoyed your stay at this amazing home, and that you all had a great time! We also appreciate your feedback. We'll review this with our team and see if there is any room for improvement. It was our privilege to host you, and we hope that you'll come back and stay with us again in the future. You're welcome any time.
Sincerely,
Siesta Key Luxury Rental Properties
This property is amazing! It completely exceeded our expectations for our family getaway. We had plenty of room (5 adults and 4 kids). The details in the kitchen and around the house, the fabulous views throughout the house, and the luxurious master bedroom and bath blew us away. We thoroughly enjoyed spending time at the pool and in the various outdoor spaces watching the boats go by. And the huge tv on the covered porch was the perfect spot to watch the NFL playoff games. Also, the property manager was extremely friendly and helpful and the check in/ check out process was super easy. Honestly couldn’t have asked for more. 10/10 recommend!
Katie M.
Stayed 5 nights in Jan 2021
Response from VrboOwner on 10 Feb, 2021
Katie,
Thank you so much for choosing our home for your Siesta Key vacation! We are so glad that you enjoyed your experience here with us, and that our home and it's location made your stay that much better! It was a pleasure hosting you, and we hope to have the privilege of hosting you again in the future. You're welcome any time.
Sincerely,
Siesta Key Luxury Rental Properties
Overall...wonderful place! Checked all the boxes. Pool was nice but got too hot a couple days so was not refreshing..A good rain helped cool it off a bit. Dock was wonderful for kids to fish. We rented a boat and used the dock to load up supplies. Kayak was fun, with the exception of a small rodent bone in it! There were a few things that needed fixing that couldnt at the time..leg on coffee table was broken, fridge drawer kept falling out. Fishing poles were there to use, but no reels. Cooler was there to use but smelled so bad and had a layer of scum in it, we bought one ourselves. We had some trouble with a door code not working, amd maintenance was very responsive to fix it. All and all, a nice place to stay with family and friends despite being a bit pricey.
Julie C.
Stayed 8 nights in Jun 2025
About the host
Hosted by Siesta Key Luxury Rental Properties
We are an owner operated rental company on Siesta Key. We manage a 58+ unit resort and single family homes. All of our properties are within walking distance to the beach and the village. We have a high focus on customer service and our primary focus is ensuring our guests have a spectacular stay with us in paradise.
Languages:
English
Premier Host
They consistently provide great experiences for their guests