Mainsail

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  • Sleeps: 10
  • Bedrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Pets: 2

Description

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!

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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.

Room Details

Room Beds
Bedroom 1
  • Queen
Bedroom 2
  • Queen
Bedroom 3
  • Queen
Bedroom 4
  • King

Amenities

Fun and Entertainment
• Games
• Kayak
• Smart TV
• TV
Essentials
• Air Conditioning
• Beach Chairs Provided
• Beach Towels Included
• Bed Linens
• Clothes Hangers
• Dryer
• Free WiFi
• Hair Dryer
• Heating
• Hospital Close By
• Hot Water
• Iron and Ironing Board
• Long Term Stays Allowed
• No Pets Allowed
• Private Entrance
• Towels
• Washer
• Wifi
Kitchen
• Baking Sheet
• BBQ Utensils
• Blender
• Coffee Maker
• Dining Table
• Dishes and Utensils
• Dishwasher
• Freezer
• Hot Water Kettle
• Ice Maker
• Kitchen Island
• Microwave
• Mini Fridge
• Oven
• Pots and Pans
• Refrigerator
• Stove
• Toaster
• Wine Fridge
• Wine Glasses
Location
• Canal Front
• Less than a 10-minute walk to the beach
• Near Ocean
• Pool Views
• Residential Street
• Siesta Key
• Water Front
• Water View
Exterior
• Backyard
• Balcony
• Boat Dock
• Deck
• Fenced Yard
• Fishing Dock
• Gas BBQ Grill
• Heated Pool
• Hot Tub or Spa
• Outdoor Dining Area
• Outdoor Kitchen
• Outdoor Seating
• Patio
• Private Pool
• Sun Loungers
Parking
• Five (5) Parking Spaces
Home Safety
• Carbon Monoxide Detector
• Contactless Check-In
• Fire Extinguisher
• Keyless Lock
• Security Camera Present
• Smoke Detector
Interior
• Bathtub
• Ceiling Fans
• Clothing Storage
• Full Kitchen
• Living Room
Things To Do
• Bird Watching Nearby
• Boating Nearby
• Fishing Nearby
• Golf Nearby
• Health Beauty Spa Nearby
• Jet Skiing Nearby
• Kayaking Nearby
• Laundromat Close By
• Marina Nearby
• Museums
• Parasailing Nearby
• Sailing Nearby
• Shopping Nearby
• Swimming Nearby
• Water Sports Nearby
• Wildlife Viewing Nearby

Rates

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Reviews

Title Guest Rating Staff Comments Date
12/10 recommend this place! Check in was easy and my two minor concerns (one of which turned out to be a me problem not a them problem) were addressed very quickly. The pool was used constantly! There was some sort of leak causing it to get green quicker than usual but it was addressed twice during our stay and the kids couldn’t have cared less regardless. The started sets came in handy since we got in late.Some things to note for your own stay: - The rear doors have very loud alarms. This is a requirement but we weren’t aware and immediately set them off when we arrived and then sat covering our ears for a solid 5 minutes until we were informed it’s a simple button push right on the alarms to silence them every time you use them. No big deal from that point on!-There was a beach wagon, chairs and towels but no other beach items for families. We bought some boogie boards, buckets and shovels and left them there for other families to enjoy! Pulling the loaded wagon on the beach was a treat, just plan to have someone push while another person pulls!-The beach is close and you could probably bike or walk depending on your guests and how much stuff you have. We drove and public parking was kind of a nightmare at certain times. The largest parking area is by Siesta Key Beach but if you try to go between 10-3 (season depending I’m sure) you’ll drive around in circles for 15 mins before you get lucky and someone pulls out.Overall we would 100% stay here again and again! Cherie 5 Thank you for choosing this property for your recent stay! I'd love your feedback on what you enjoyed and what I can do to improve the experience for future guests. Thank you 03/29/2026
Fantastic house and location Verified traveler 5 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! 02/06/2026
Great place to get away from everything! We have stayed other places that say they are private, but are actually right next to other properties. This place is exactly as described, with great amenities. Would stay again for sure. Julie 5 06/19/2025
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 5 We are so happy to hear you enjoyed yourselves and appreciate you sharing your experience! We hope to host you again in the future! 05/27/2025
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 5 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. 04/03/2025
Excellent vacation! Kip 5 Hi Kip! We are so glad that you enjoyed the view at Mainsail, please come back and visit us again soon! 01/12/2025
“Over the top”!!! Sallie 5 Thank you for your review! 12/02/2024
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 5 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! 09/16/2024
Very nice property for family get together. Ages 10-84 did well!!! ANdrea P. 5 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! 🏡❤️ 07/07/2024
We enjoyed our visit. The house was beautiful! Joanne 5 Happy to hear you had a great time! 😃 The house is indeed beautiful. Hope to host you again, Joanne! 🌸🏡 06/07/2024
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. 5 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. 05/15/2024
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. 5 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! 03/23/2024
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. 5 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! 02/16/2024
Beautiful Open Space with Dolphins Swimming by the Deck. Amazing Location Great Support Andrew H. 5 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. 01/12/2024
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. 5 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! 10/09/2023
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. 5 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! 04/01/2023
Excellent week at the house! Very relaxing! Gots all the amenities! Great views! kawveh n. 5 Thank you for taking the time to share your experience with us, Kawveh. We are glad you enjoyed your stay and hope to host you again soon! 03/21/2023
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. 5 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! 02/11/2023
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. 5 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! 01/13/2023
What an amazing place, didn't even wanted to leave to go anywhere. Got everything for you to stay there and enjoy your vacation. What stood out the most is the kitchen, has everything for you to cook for a big family. Hot tub works great, amazing view. Will be planning to come back 100% Julian 5 Julian, thank you for taking the time to share your experience with us. We are thrilled to hear you enjoyed the home, kitchen, and hot tub. We can't wait to host you again! 11/30/2022
Amazing property, very comfortable and views are incredible. Would highly recommend. Kaveh 5 Kaveh, thank you for taking the time to share your experience with us. We are happy to hear you had a comfortable stay and enjoyed the property. You were a wonderful guest, and we would love the opportunity to host you again in the future! 09/22/2022
My friends and I loved staying here for my friend's birthday! Lots of space for everyone to enjoy especially since it was raining half the time. The pool is spacious and great for a big group too. They are stricter on noise complaints even before the noise ordinance at 10pm-7am but still had a great time. We may make this an annual thing. Rachael 5 Rachael, we are thrilled to hear you and your friends enjoyed the house and pool. You were fantastic guests, and we look forward to hosting you again! 09/11/2022
The renting experience was easy and great. Maribel H. 5 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! 09/09/2022
The house was even better in person! Our family enjoyed our weekend getaway! Each bedroom on first and second floor has their own bathroom. So if you have a group of 10 like we had, the people in the bedroom by the pool will have to wait for people from one of the bedrooms with full bathroom to take a shower. But there is an half bathroom by that bedroom and another half bathroom by the living room and kitchen area. The house was immaculate. There’s everything that you can possibly need in the kitchen to cook. Nice big fridge. Very modern appliances. Big screen TV everywhere. The view is outstanding at every level in the house. Very quiet neighborhood. If I could, I would return every month! Marie-Irvine B. 5 Marie, 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! 08/29/2022
Great location to relax with a group Michelle M. 5 Michelle, we are happy to hear that you enjoyed your stay. We hope to host you again in the future! 08/10/2022
A great property - beautiful views, pristine condition, perfect for our family of 4 with room to spare. Craig S. 5 Craig, we are so happy to hear that you had such a great stay! We hope to host you again in the future! 06/09/2022
This is an amazing property and the manager was great. We loved all the things to do on the key and in Sarasota. They were super helpful and we will defiantly book again. Candace W. 5 Candace, thank you for taking the time to share your experience with us. We are glad you enjoyed your stay and communication with our team. We hope to host you again sometime soon! 01/25/2022
Very clean and fantastic location. Verified traveler 5 We are glad you enjoyed your stay and hope to host you again sometime soon! 01/02/2022
This house is just perfect. We watched dolphins playing right in front of us. We had plenty of luxurious house to accommodate three generations and everyone enjoyed the kayaks, biking to the beach,bbqing, and relaxing all together. The kitchen was well stocked with everything we needed to make meals together and the master suite is really gorgeous! Will definitely return. Catherine 5 Dear Catherine,

Thank you so much for your glowing review of our 'Mainsail' property! We're so delighted to hear that the home was enjoyed by all ages, and that the miraculous views of the Intracoastal were made that much better by the dolphins passing through! We are also happy to hear that the home, and all of its amenities, made for a well enjoyed family vacation. It was an absolute pleasure to host you, and we hope you come back to visit us again in the future!

Sincerely,
Siesta Key Luxury Rental Properties
12/06/2021
The house was beautiful and perfect for a getaway weekend. Great location. Raelynn H. 5 Dear Raelynn, Thank you for reviewing your recent stay with us as a 5-star vacation! We are thrilled that our 'Mainsail' property suited you and your group so well and that you enjoyed the home's location and breathtaking views of the Intercoastal Waterway. Thank you for trusting us with your vacation and we hope to see you again soon! Best regards, Siesta Key Luxury Rental Properties 10/15/2021
The house is wonderul. Right on the bay and the amenities are all top of the line. I would rent it again. lance D. 5 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 10/04/2021
Amazing house and amazing location! george m. 5 George, Thanks so much for the 5-star review! We are so happy to know that you and your group enjoyed this beautiful home along the intercoastal waterway and it's convenient location to the beach and the amenities near the South bridge onto Siesta Key! It was our absolute pleasure to host you, please come back and see us anytime! Sincerely, Siesta Key Luxury Rental Properties 09/10/2021
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. 5 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 06/11/2021
We rented this house for my birthday and absolutely loved it. It is a very large property and for the two families that stayed there with infants - it worked out very well. If you want to go to the beach everyday, this probably isn’t the place for you but if you want a large house with calming views of the water and the boats, this will do just fine. We had a problem with the washer being broken but it was fixed within 2 days of getting to the property and the property manager let us use another property they own to do the babies’ laundries. Good communication throughout. Joonhyun K. 5 Joonhyun, Thanks for reviewing your recent stay with us! Our Mainsail property is truly a one-of-a-kind property, located directly on the intercoastal waterway and on a secluded and private residential street. I do apologize that the washing machine unexpectedly stopped working, but I am glad to know that our property management team quickly offered a solution and was able to fully repair the washer within 2 days! As you may or may not know, because of COVID and many business shutdowns, it has been extremely challenging to find parts and materials for appliances for our homes, so we are really happy this worked out this efficient. We are also really glad that our temporary solution to this problem, i.e. using another home’s washing machine instead, was something that worked for you and your travel companions. As always, we appreciate all of your feedback as it helps us to improve. We hope to see you in beautiful Siesta Key again soon, you’re welcome any time! Sincerely, Siesta Key Luxury Rental Properties 06/10/2021
We absolutely loved this property. There were 2 families with 10 people in total and everyone couldn't get enough. The pool and hot tub were fabulous and we loved watching the boats go by. It's a nice walk to downtown and we also took full advantage of the bikes and beach cart. We would definitely stay here again. Tara F. 5 Tara, Thanks so much for your 5-star review of your recent stay with us at our Mainsail property! We're so glad you enjoyed this home's amazing location along the Intercoastal and felt it was a perfect fit for everyone traveling in your group! We hope to have you return to stay with us again soon. Best, Siesta Key Luxury Rental Properties 04/24/2021
The house and amenities were great! We were able to spread out and enjoy different activities at the same time such as biking, fishing, sitting by the pool and cooking. We can’t wait to visit again next year! Sherri S. 5 Sherri, We can't wait to host you again next year! We are so glad that you and your family had a wonderful time here with us and that our home was the perfect place for your vacation! We apprecaite your feedback! Sincerely, Siesta Key Luxury Rental Properties 03/10/2021
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. 5 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 02/10/2021
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. 5 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 12/21/2020