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SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE

Photo gallery for SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE

Beach
Aerial view
Interior
Exterior
Pool

Reviews

9.8 out of 10
Exceptional
8 bedrooms8 bathroomsSleeps 28

Popular amenities

  • Air conditioning
  • Pet-friendly

Explore the area

Map
Sarasota, FL
  • Crescent Beach
    ‪6 min walk‬
  • Siesta Key Beach
    ‪17 min walk‬
  • Point of Rocks
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪21 min drive‬

Rooms & beds

8 bedrooms (sleeps 28)

Bedroom 1

2 Single Beds

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

1 King Bed

Bedroom 6

2 Single Beds

Bedroom 7

1 King Bed

Living Room 1

4 Single Futons

8 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Bathroom 8

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

About this property

SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE

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, brand new inside (8 Bed/8 Bath sleeps 28 for a family reunion / wedding etc.) cottages! 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 were all fully renovated inside in December, 2024. Each cottage has 2 bedroom, 2 bathrooms (each with a heated bidet), and sleeps up to 7. 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!

Property manager

Marc Wolff

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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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

Events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site. Maximum attendees: 99
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Siesta Key

Located in Siesta Key, this holiday home is 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. Looking to enjoy an event or a game while in town? See what's happening at Stardust Event Center or Sarasota Kennel Club. Discover the area's water adventures with scuba diving, snorkelling and waterskiing nearby, or enjoy the great outdoors with cycling.
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
  • Turtle Beach - 4 min drive - 3.5 km
  • Lido Beach - 22 min drive - 20.5 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬10 min walk
  • ‪Hooters - ‬4 min drive
  • ‪Daiquiri Deck South Siesta Key - ‬11 min walk
  • ‪Culver's - ‬4 min drive

Frequently asked questions

Does SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE?

Check-in begins at 4:00 PM.

What time is check-out at SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE?

Checkout is at 10:00 AM.

Where is SIESTA KEY #1 BEACH USA: GROUP OF 4 COTTAGES CAN BE RENTED TOGETHER OR SEPARATE 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.
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Rating 10 - Excellent. 101 out of 115 reviews
Rating 8 - Good. 12 out of 115 reviews
Rating 6 - Okay. 2 out of 115 reviews
Rating 4 - Poor. 0 out of 115 reviews
Rating 2 - Terrible. 0 out of 115 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Kamil M.

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

Cozy cottages

Stay was great, very intimate cottage for families and a block from the beach. Will be coming back
Stayed 3 nights in Aug 2024

10/10 Excellent

Brenda S.

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

Great location

These cottages worked out well for us. We had 5 high school seniors in one cottage and we were a few steps away in another. Having our own pool and hot tub was great as well. It gave the guys a sense of freedom without parents in the space and I was happy not to have messy teens in my space. We also had a short walk to the great local restaurants. The only downside was a felt the kitchen was a tiny bit under stocked but truly manageable. Thank you for a great week.
Stayed 7 nights in Apr 2025

10/10 Excellent

tylerbpolk

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

Amazing Spot

The property was great. Awesome location! Dave was incredibly helpful throughout our stay. Highly recommend!
Stayed 7 nights in Mar 2024

10/10 Excellent

Jinell C.

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

Perfect stay

The Cottage was amazing and so was Dave! The cottage was stocked with goodies and beach supplies. Beach and restaurants were steps away. We will be back next year!!
Stayed 2 nights in Sep 2024

10/10 Excellent

Alysha S.

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

Great week!

We rented two cottages for our Spring Break visit. Check-in was easy and Dave was in constant contact with us. They have worked very hard since the hurricane in 2024 and the property is basically brand new. It was a quiet and safe spot and our kids loved playing football and Spikeball on the newly installed turf after easy visits to the beach and pool. The outdoor seating was great for sipping coffee in the morning or playing cards together in the evening. We will be back next year!!!
Stayed 7 nights in Mar 2025

10/10 Excellent

Rae N.

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

Cute Little Cottages - Perfect for Group/Multiple Families!

We rented 3 of the 4 cottages for a family wedding and had an absolutely wonderful stay! The location was perfect—everything we needed was just a short walk away, making it so easy for everyone to explore and enjoy our trip. The property itself was spotless, great design and had everything we needed (and then some!) A very important detail for us, was all of the parking! (we needed it!) Marc & Dave were absolutely wonderful to work with—super responsive, friendly, and went above and beyond to ensure our family had an unforgettable experience. We can’t wait to come back!!!
Stayed 5 nights in Jan 2025

10/10 Excellent

Shannon F.

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

A perfect holiday location!

Our large group rented all cottages and had a wonderful trip! The ease of going to and from the beach was perfect and the pool areas allowed for us to be outdoors together once the sunset. Thank you for sharing your property with us!
Stayed 7 nights in Nov 2023

10/10 Excellent

Adelle K.

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

Great place right near the beach!

Highly recommend. Fantastic location and has all beach amenities, as well as bikes. Property manager is super responsive with lots of tips for a great trip. We will be back for sure!
Stayed 2 nights in Nov 2023

8/10 Good

Sam C., Rochester

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

Great location

The cottages are located conveniently on the south end of Siesta Key, which makes traffic less of an issue. The beach is a short walk and the food in the area is amazing. We will be coming back next year.
Stayed 5 nights in Mar 2020

10/10 Excellent

Carrie D.

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

Quiet Beach Getaway

This was great for a family get together. Walking distance to the beach with beach chairs and activities provided. There's a small pool great for winding down and ending the evening.
Stayed 4 nights in Dec 2022

10/10 Excellent

Gwen G.

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

Relaxing Long Weekend

We stayed over the weekend as our kids had a swim meet in the area. The accommodations were perfect as it allowed us to relax and unwind in our free time. We rented a golf card to add a little fun but enjoyed the pool, hot tub, quiet in the evening and walking distance to the beach. It was nice having the kitchen area so we could make our breakfasts, and the washer and dryer was a huge add on for us as we had lots of towels from the swim meet. We will defiantly be returning in the future.
Stayed 2 nights in Jan 2025

10/10 Excellent

Jessica B.

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

So perfect for us

We had a great time at our cottage. Zero complaints. Loved how close it was to everything. Would stay again, pool was ideal for small kids.
Stayed 3 nights in Jan 2023

10/10 Excellent

Tiffanie L.

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

Great time at Siesta Cottages!

Highly recommend! Mark and Dave were very accommodating. The property was beautiful with great location to the beach and trolley. Would highly recommend.
Stayed 3 nights in Aug 2023

10/10 Excellent

Michelle S.

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

LOVELY PLACE

Great property, very clean and had everything we need. Rented 3/4 properties for a big birthday weekend. Highly Recommend!
Stayed 2 nights in Aug 2019

10/10 Excellent

Nanci W.

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

Perfect getaway week

From booking to check out- this was perfect for us. Loved the keyless entry, plenty of beach equipment (some regular beach chairs , not just low ones which my knees appreciated) very clean and stocked with paper products- huge help. Loved how convenient the trolleys are. Communication was excellent!
Stayed 4 nights in Feb 2024

10/10 Excellent

Brittany O.

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

Family Spring Break

The proximity to the beach was fantastic! The communication was wonderful. We enjoyed a two cottage stay with 11 family members ranging in age from 4 to 69. There were accommodations for everyone. The beach gear on property is great to have access to use. We would stay here again!
Stayed 7 nights in Mar 2024

10/10 Excellent

Sheila O.

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

Great Place!!!!

We had an amazing stay at this property!!! The location was great, very close to the beach. The property was very clean and cozzy. Additionally, it went above and beyond in providing us with beach chairs, beach towels, beach cart, bicycles, etc. We will definintely be coming back!
Stayed 4 nights in Aug 2020

10/10 Excellent

Carolina B.

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

A great escape!

Was a perfect place for us to get away from Miami and enjoy the laid back life of Siesta! Families had fun, teens felt independent taking the trolley into town for shops and ice cream. We were four families so it was great that we could hang together but have our own independent spaces. The set up also makes it comfortable in case you do not know the other staying around you. Thank you for your support and the great stay!
Stayed 3 nights in Aug 2024

10/10 Excellent

Kathy W.

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

Great location

Great walking distance to beach, dining etc and trolley makes it even easier to get to villages. Cottages are nice bit could use a deep cleaning and some paint. Dave was great to work with, very available. We had a fun vacation!!
Stayed 3 nights in Dec 2022

10/10 Excellent

Eduardo V., Miami, Florida, USA

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

Great property to rent.

These cabanas are well located, well furnished, nearby the beach and have several furniture pieces inside and outside. The pool was very clean and a service person added chlorine as soon as we arrived. We will rent again!
Stayed 3 nights in Aug 2019

8/10 Good

CHERYL S.

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

Well equipped cottage

Equipped with everything you need, bicycles were a bonus. Host was very nice and responsive. Only concern was beach access close to cottage was within walking distance but public beach area was small.
Stayed 3 nights in Apr 2024

10/10 Excellent

Michael J.

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

Perfect Location to walk to the beach!

We enjoyed our stay on Siesta Key! The property manager welcomed us and made sure we had all that we needed. The weather was cool so we didn't enjoy the pool or hot tub, but they would be fun to use. The walk to the beautiful beach was less than three blocks.
Stayed 5 nights in Jan 2024

8/10 Good

Sharon R.

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

Crescent st

Comfortable ,manager friendly
Stayed 7 nights in Jul 2023

10/10 Excellent

Tammy H.

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

Great value

Everything was clean and we really appreciated all the convenient amenities, such as beach towels, chairs and umbrellas, along with a wagon to transport it all. I was concerned as it was our first time not staying on the beach but the walk was short and easy. Manager was attentive and very friendly.
Stayed 3 nights in Sep 2023

10/10 Excellent

Marsha B.

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

Family Oasis

We really enjoyed staying in these cottages. It was nice to be together and also have our own space. We spent a lot of time at the beach and in the pool. It was nice to have plenty of beach toys and wagons to use to make the short walk to the beach. The property manager was kind and made himself available to answer any questions we had.
Stayed 7 nights in Oct 2023

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 7) 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

A full service real estate rental management company will be there for you for whatever you need. They are first class and are there to accomodate your needs. Entry to each cottage is via electronic key pads so no need to carry any keys!