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SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE

Photo gallery for SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE

Beach
Exterior
Interior
Pool
Terrace/patio

Reviews

9.8 out of 10, Loved by Guests
Top 10% based on
4 bedrooms4 bathroomsSleeps 7

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
Sarasota, FL
  • Place, Crescent Beach
    ‪6 min walk‬
  • Place, Siesta Key Marina
    ‪9 min walk‬
  • Place, Siesta Key Beach
    ‪17 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪31 min drive‬

Rooms & beds

4 bedrooms (sleeps 7)

4 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

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!
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Sarasota, FL

What's nearby

  • Crescent Beach - 6 min walk - 0.6 km
  • Siesta Key Marina - 9 min walk - 0.8 km
  • Siesta Key Beach - 17 min walk - 1.5 km
  • Gulf Gate Mall - 4 min drive - 2.8 km
  • Lido Beach - 24 min drive - 17.4 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 26 min drive

Restaurants

  • ‪Panera Bread - ‬3 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Culver's - ‬4 min drive
  • ‪Hooters - ‬4 min drive
  • ‪Five Guys - ‬3 min drive

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 28 Mar 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 17 May 2026 start from £277, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 32 reviews
Rating 8 - Good. 4 out of 32 reviews
Rating 6 - Okay. 0 out of 32 reviews
Rating 4 - Poor. 0 out of 32 reviews
Rating 2 - Terrible. 0 out of 32 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Vicky E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay! Awesome location. Very relaxing. Host was very informative! Would highly recommend.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

John P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location is perfect for going to the beach. Great communication from our host. Nice, clean unit. Highly recommended.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

John P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Florida getaway close to the beach

Very nice accommodations with a variety of activities that create memories.
Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

Heather G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place

The cottage is wonderful. The pool is great though small. Our family really enjoyed it. Dave was great to deal with.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Lisa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta key’s vacation

We loved it here!! Very clean!! Great location!!
Stayed 4 nights in Mar 2024
Verified

10/10 Excellent

Barbara H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Nicholas T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Easy getaway

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
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Anita B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

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.
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Leslie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sweet stay

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!
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Deborah G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mother’s Birthday Celebration!

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.
Stayed 4 nights in Feb 2024
Verified

10/10 Excellent

Kristen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous rental!

We loved the property! The communication was great and we really enjoyed being there. It has everything you could need! We will def be back.
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Kattrina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short but sweet

Cute little cottage close to all the fun in Siesta. Great communication by property manager!!
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Jennifer W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday trip

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!
Stayed 3 nights in Apr 2024
Verified

8/10 Good

Sarah M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely cottage and stay

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.
Stayed 10 nights in Jan 2025
Verified

10/10 Excellent

Meg H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun in the sun

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!
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Anita T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta Key as it used to be.

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.
Stayed 7 nights in Jan 2024
Verified

10/10 Excellent

Diana C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely Perfect!

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!!
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Dennis C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic

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!
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Jenny H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Jan 2024
Verified

10/10 Excellent

Courtney P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely Brilliant

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!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Rob M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The perfect anniversary weekend!

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.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Alison M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

70th birthday in Siesta Key

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!!
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Katie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend get away

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!!!
Stayed 2 nights in Apr 2023
Verified

10/10 Excellent

Annette A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and coozy cottage!

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!
Stayed 2 nights in Dec 2022
Verified

10/10 Excellent

Todd B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and I would stay there again

All around excellent
Stayed 7 nights in Apr 2022

About the host

Hosted by Marc Wolff

Host profile image
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!
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