SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE
RATES ARE FOR 1 COTTAGE: IF YOU WANT MORE THAN THAT, JUST MESSAGE ME AND THE RATES ARE JUST MULTIPLIED TIMES THE NUMBER OF COTTAGES YOU WANT, SO IF YOU WANT THREE FOR EXAMPLE, JUST MULTIPLY THESE RATES TIMES 3. Thanks!
4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) with only a 4 minute walk (no major streets to cross) to the #1 Beach in the USA: Siesta Key. First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!
Rent all four (8 Bed/8 Bath sleeps 24 for a family reunion / wedding etc.! The open aired free Siesta Key Breeze Trolley goes right by the properties to take you all over the island! Full service real estate management company servicing the property 24/7. Free washer / dryer in each house. During certain months the minimum stay can vary up to a 7 day minimum. Please message me for specific date requests. If there is a 7 day minimum during the time period you request there might be more flexibility the closer to the dates. So please don't hesitate to message me and it's possible we can work something out. Thank You! NOTE: The homes can be rented separately or 2/3 or 4 together. Please note that the calendar reflects available with at least one cottage. Renting all four at the same time will not be possible if just one of the cottages is already booked. So if you see availability on the calendar that doesn't necessarily mean that all four are available. Please inquire about availability as to how many cottages you are looking to rent and the dates. I respond pretty quickly via the messaging system. Siesta Key ges very busy as do these properties so please the more notice you can give the better! Thanks!
The Cottages are in the perfect location: The beginning of the famous Siesta Key Beach in an area called Crescent Beach, which I believe is the most beautiful part of Siesta Key. Also, on your way you'll find that after driving over the draw bridge to Siesta Key, you get to turn left instead of right and that helps you avoid most of the traffic! Another quarter of a mile and you are there! The cottages have 15 free parking spots within a few feet of your front door! Everything is only one story: No stairs / Easy access. No physical keys are required. We give you the electronic door code prior to check-in. The kitchen is stocked with all the tools/pots/pans etc. you will need if you prefer to stay in and cook and you also have your own gas grill with an outside seating area. Also included is your own washer and dryer (washer pods and dryer sheets too) and a storage area filled with beach toys, chairs, bicycles. The pools are heated year-round at 87 degrees (including a wading area where you can relax and have a drink while being submerged in only a few inches of water) and have plenty of seating. There is free beach yoga close by several days a week on Siesta Key. The Cottages are in walking distance from the South Village, which has plenty of delicious restaurants, bars and shops, including a new coffee shop (coffee there is amazing!). Also in walking distance is the new “Daiquiri Deck” (Several stories high so you can have a cocktail while watching the sunset from the upper deck) and “Miguel’s” family restaurant (one of the best around and family owned for over 40 years!) among many others. “Ophelia’s on the Bay” is down the street on Siesta Key towards Turtle Beach and thought my many (including myself) as one of the best restaurants on the planet! We know the people at both of these restaurants and would be happy to connect you and make sure they take first class care of your experience! We can also give you plenty of other recommendations for restaurants and other “stuff” to do on Siesta Key and around town. In addition, we include helpful information in your welcome packet which will get you started! The beach is very close and easy to get to from the Cottages: Only a four-minute walk on a quiet street. If you want to go to the north Village on Siesta Key and don’t feel like taking the bike, you could drive (only 2 miles away) or take the free Siesta Key Breeze Open Air Trolley: It drives right by The Cottages continuously!
Cottages can be rented separately or together. Everything in the property is accessible to customers. There are 4 cottages, 2 pools, 2 hot tubs, and 2 outdoor gyms. Those with at least two cottage rentals will have exclusive access to their own pool, hot tub, and outdoor gym. Those with one cottage might have to share a pool, hot tub and outdoor gym with the other cottage.
Minimum stay of 2 nights will vary: During high season a minimum stay of one week will be required. Please inquire for more specific dates / information.
Save Money at the Cottages (and other additional benefits)!
No rental fees for bikes or beach equipment (chairs, umbrellas, toys)!
No beach transportation fees: The beach is a 4 minute walk on a quiet street!
No parking fees: Free parking right in front of your cottage!
No chance to lose your keys: Cottages have digital key pads
No steps to climb to get into or around the cottages
Thank You!
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Siesta Key
Located in Siesta Key, this holiday home is near 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.
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 26 min drive
Restaurants
Panera Bread - 3 min drive
McDonald's - 3 min drive
Hooters - 4 min drive
Culver's - 4 min drive
Captain Curt's Crab & Oyster Bar - 10 min walk
Frequently asked questions
Does SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE on 4 Apr 2027 start from AU$632, 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 SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE pet-friendly?
No, pets are not allowed at this property.
How much is parking at SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE?
On-site parking is available at the property.
What time is check-in at SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE?
Check-in begins at 4:00 PM.
What time is check-out at SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE?
Checkout is at 10:00 AM.
Where is SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE located?
Situated near the beach, this holiday home is within a 10-minute walk of Point of Rocks and Crescent Beach. Siesta Key Beach is 1.1 mi (1.8 km) away.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Very nice accommodations with a variety of activities that create memories.
John P.
Stayed 6 nights in Jun 2025
Response from VrboOwner on 6 July 2025
Hi John. Thanks so much for your kind review. We do make every effort to make guest stays special. Hopefully you can make it back to stay with us in the future. Take care. Marc and Dave
The cottage is wonderful. The pool is great though small. Our family really enjoyed it. Dave was great to deal with.
Heather G.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 17 Mar 2025
Hi Heather. Thanks so much for your kind review. Great that you and your family had a good time. We do hope you can return in the future!!! Marc and Dave
Wonderful cottage in a nice quiet area, close to beach.
We had a wonderful time, thank you to Dave and Marc for a very easy check in/out process. Cottage had everything we needed for a fantastic mini get away. Siesta Key is a very nice laid back island to spend a few days or a week, a lot to do and beaches are clean and beautiful!. Will stay here again.
Barbara H.
Stayed 2 nights in May 2024
Response from VrboOwner on 8 May 2024
Barbara. Thanks so much for your kind review. We are very happy that we could make your stay enjoyable and hope to see you again. Take care!! Marc and Dave
Fantastic experience. Lots to do and the hosts took great care of us. Everything you could need for a relaxing weekend, especially the pool and kids toys
Nicholas T.
Stayed 3 nights in May 2024
Response from VrboOwner on 28 May 2024
Hi Nicholas. Thank you for your kind review. We try to create an enjoyable experience for every guest. So happy you had a good time here. You are welcome back anytime. Marc and Dave
We had such a great time in Siesta Key and staying at this property. Marc the owner was great to deal with. David, who managed the property was an awesome guy. He was easy to reach and took care of anything we needed. His daughter was also so nice. We would definitely stay here again.
Anita B.
Stayed 3 nights in May 2024
Response from VrboOwner on 5 June 2024
Hi Anita. Thanks so much for your kind review. We are so happy that you had a great time here. Hopefully you can return in the future. Take care! Marc and Dave
Fabulous stay at the Cottages. Perfect location to walk to the beach and restaurants! Our host Dave was amazing! If we needed anything he got it for us, even a bike! Great stay❤️. Returning next February.
Deborah G.
Stayed 4 nights in Feb 2024
Response from VrboOwner on 3 Mar 2024
Hey Deborah. Thanks so much for your great review and very happy you are returning next year. You will be back before you know it. Take care!!
Marc and Dave
We enjoyed the cottage and all of the amenities offered to us. Property management was attentive and went out of their way to offer customer service. We are thankful for the opportunity to stay in Siesta and explore a new area of Florida!
Leslie T.
Stayed 4 nights in Jun 2024
Response from VrboOwner on 9 June 2024
Hi Leslie. Thank you for your kind review. We try to make every guest's stay a great one. So happy that you had a great time here. Hopefully you can return in the future. Take care! Marc and Dave
This property was perfect for our beach trip! There were 4 couples, and we shared 2 of the cottages very comfortably. Marc and Dave were so responsive, courteous and friendly! The cottages were very well stocked and clean. We will definitely book again there for our next trip to Siesta Key!
Jennifer W.
Stayed 3 nights in Apr 2024
Response from VrboOwner on 23 Apr 2024
Hi Jennie. Thanks so much for staying with us. Very happy we could make your stay a great one. You are welcome back any time!
Marc and Dave
The cottage was great, most was new having been refurbished. Location was 5km from Siesta Village either an hour walk or accessible by trolley. Initial communication was quite sparse which if travelling from outside the US can be stressful but once there was fine. Beach was gorgeous and property provided beach chairs which was really appreciated. We were a party of 4, I think any more and the cottage would feel really cramped.
We had a wonderful time at the cottages. Quick walk to the beach. The cottage had everything we needed. Dave went above and beyond with any questions we had. We will definitely be back!
Spacious, well supplied and extremely clean cottage environment surrounding a landscaped courtyard with two small but inviting pools. Excellent communication and accommodation through the whole stay. Short walk to Crescent Beach or a short drive to Turtle Beach with plenty of parking. Several nice Island-style restaurants and groceries nearby. Highly recommend.
Anita T.
Stayed 7 nights in Jan 2024
Response from VrboOwner on 4 Feb 2024
Thank you so much for your kind review. We thank you for allowing us to host you while in Siesta. Hope you come back soon!
Marc and Dave
The property was beautiful & the location perfect. Walking distance to the beach. It was super clean, the pool and hot tub were super nice. There was everything you needed and more. Marc and Dave were great! Dave was super helpful,kind,caring and made our trip so much easier! We will definitely be going back!!
Diana C.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 28 Oct 2023
Diana. Thanks for your kind review. So happy we could make your stay special. You are welcome back any time. Marc and Dave
This was a very nice place to stay.
We were there on business and this was very convenient to get in and out of. You CANNOT beat this location!
You don't need to leave this place as it has everything but if you do everything is easy to get to. Walk to beach, dining, etc.
Park your car and park yourself!
Dennis C.
Stayed 3 nights in Nov 2023
Response from VrboOwner on 7 Nov 2023
Hey Dennis. Thank you for the kind review. So happy we could make your stay enjoyable.
Marc and Dave
Great place to stay, A+ communication with manager
This is a great place to stay when visiting Siesta Beach area. It's not right in the middle of things so it's quiet and close to the beach, and shopping and restaurants are a short drive away. It's easy to find with lots of parking.
The place is a bit dated with older fixtures, furniture and linens that you don't see in the photos, but they are all clean.
Be aware the pool is a lap style pool, no deeper than 4 feet, but's it's clean, warm and there is a lovely hot tub as well.
The communication with the owner and property manager was A++. Friendly and accommodating.
This place has everything you would use in your own home. It was our very first time ever being in Florida and this place for sure made it worth it! I loved the little amenities that came with the property. It is GREAT for children and adults. I would highly recommend to anyone looking for a small little vacation. Also I wanted to say that the manager and owner took great care of us! They make sure you have everything you need and they answer back quickly. This is a lovely place and it made the 12 hour drive worth it. We will definitely be back!
Courtney P.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 13 Oct 2023
Courtney. Thank you for your kind review. So glad we could make your stay special. You are welcome back any time !! Marc and Dave
The property is just as advertised. We found the place very clean and the perfect fit for us and our weekend. Quiet, comfortable, close to the beach, nice pooln and good location. We took the trolley to Siesta Village for dinner and drinks which was a lot of fun.
The property manager Dave was awesome. No one was in the unit the day before us so we were given the opportunity to check in early and even offered a chance to check out late. Dave checked with us a couple times to see if we needed anything and gave us a couple tips Bout the area and the trolley. Great communication! We plan to stay here again and highly recommend the Cottages.
Rob M.
Stayed 3 nights in Aug 2023
Response from VrboOwner on 28 Aug 2023
Thank you for the wonderful review. So happy that we could help you enjoy your time here. You are welcome back any time! Marc and Dave
We stayed at the cottages and rented the two next to each other. We were celebrating my mom’s 70th birthday!! We loved being walking distance to the beach but also getting to enjoy the pool after we got back from beach days! Dave and Marc are amazing to deal with, both our great communicators and so helpful and accommodating! The best part of this place is the details: they have beach wagons to make it easier to get your stuff to the beach, there were pool floats and beach toys, bikes, beach towels, and even citronella candles for when you enjoy the patio! We loved that each unit had its own patio furniture and outdoor table and it is tucked back so it feels private from the other units. We would love to come back, was a great family weekend!!
Alison M.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 24 Oct 2023
Hi Alison. Thank you for your kind review. We are so happy that you enjoyed a very special mom's bday. Thanks again for staying with us. You are welcome back any time.
Marc and Dave
We spent two nights in the condo and were pleased with everything overall! The manager was super helpful with the check-in process; provided lots of details about the area; answered text questions promptly; and gave us a late check-out. The location was close to the beach, about a 7 minute quiet walk. There was a wagon, chairs and beach towels provided (the chairs were not low to the ground, they were more tall like bag chairs). We did not use the bikes, but they were in the process of putting some new ones together for our unit.
We enjoyed the covered porch area which had nice new furniture but we did not use the pool or hot tub area. The pool was very small and shared with another unit; it was located right outside the other unit and made us feel like we would be intruding their space.
We appreciated the air filter and the cold A/C inside, and liked the the white noise it provided. Our bed was comfortable and the bedroom closet was spacious with plenty of hangers. It was nice for each bedroom to have its own bathroom!! The kitchen seemed well stocked with essentials, though we did not cook or use the dishwasher (short trip…lots of dining out!). We liked the welcome basket of chocolates, potato chips and water in the fridge :)
It was about a 10 minute walk to the closest restaurant and bar area. There were maybe 4 restaurants, a couple little shops and a 7-Eleven. We did not use the trolley, since you had to wave it down on that part of the street and it didn’t seem to go by all that often. We did use the Frog Bus free transportation shuttle…saw the phone number on the bus and they were super quick to come get us. They work for tips and it was well worth it! We took it up to Siesta Key Village (not walkable from the condo) and it was about a 15 minute drive.
Overall we would recommend the condo, and would stay again. If you have a big group and could rent out all four units, it would be a great spot!!!
We loved the property. First off the communication from Dave was excellent. We told him we would be early and he rushed the cleaning so we could get in early. The unit is completely redone with great bathrooms and kitchen. Nice space. One of the best things is all the outdoor space nice covered patio with plenty of comfortable furniture. There is also a private back area with a gas grill, fire pit and more furniture. The beach is very close just a five minute walk and you are on the beautiful Siesta Key sand. Provided beach chairs and umbrella were great. You can walk to a few great restaurants. Would definitely stay again!
Claire C.
Stayed 2 nights in Apr 2026
Response from VrboOwner on 29 Apr 2026
Hi Claire. Thanks so much for staying with us and the great review. We do try to make guest stays special. Very happy you had a great time. Hope you can make it back our way in the future!!
Location was great, cottage had everything we needed inside and was spacious with lots of room. The pool was heated and the kids enjoyed it. Will definitely stay again!
Annette A.
Stayed 2 nights in Dec 2022
About the host
Hosted by Marc Wolff
Hello, I am the owner and president / CEO of a financial services firm and have been in the industry for 30 years. I also own some real estate around town. I am a marathon runner and for decades have run on Siesta Key Beach. Siesta Key has been rated #1 beach in the USA many times and even top 5 in the world several times. It's magical in many ways. The cottages are in my favorite area of Siesta Key, and when I ran by them one day and saw the for sale sign, I couldn't resist. I'm excited to share my love for this area with many guests in the future!
Why they chose this property
The 4 Siesta Key Cottages are vibrant, festive, newly decorated 2 BED/2 BATH (sleeps 6) pool homes. They are within 4 minutes walking distance to the gorgeous Siesta Key beach access (no major roads to cross). Point of Rocks, the closest area of the beach, is the most notable beach access for sunbathing, paddleboarding, kayaking, snorkeling and fishing because of the amazing natural limestone formation that juts out across a shallow soft sanded bottom.
Private porches and seating in the lighted, lush, tropical landscape are available for those quiet moments everyone needs. You’ll struggle with the decision to go down to the country’s #1 rated beach, chill in the pool, or go to the Village, all within easy walking or biking distance.
The cottages have exclusive access to the heated pools with a “sun shelf”. The interior consists of beautiful new décor, flat-panel, wall-mounted TVs in all bedrooms and living areas, Netflix, Roku, and Pandora entertainment. Fine linens, towels and everything else are truly “first-class” here. Private washers / dryers and barbeque grills are available for your convenience in each unit. Each cottage has their own “toy” closet filled with an array of complimentary bicycles and beach equipment. Free private parking is also included.
True Hepa/Carbon filter air purification unit standard in all cottages. Great for those with allergies. Enjoy clean air health benefits. Don't let dust, pollen, viruses ruin your vacation!
Thank You!
What makes this property unique
Private porches and seating in the lighted, lush, tropical landscape are available for those quiet moments everyone needs. You’ll struggle with the decision to go down to the country’s #1 rated beach, chill in the pool, or go to the Village, all within easy walking or biking distance.
The cottages have exclusive access to the heated pools with a “sun shelf”. The interior consists of beautiful new décor, flat-panel, wall-mounted TVs in all bedrooms and living areas, Netflix, Roku, and Pandora entertainment. Fine linens, towels and everything else are truly “first-class” here. Private washers / dryers and barbeque grills are available for your convenience in each unit. Each cottage has their own “toy” closet filled with an array of complimentary bicycles and beach equipment. Free private parking is also included.
Entry to each cottage is via electronic key pads so no need to carry any keys!