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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

  • Parking available
  • Air conditioning
  • Pet-friendly
  • Gym

Explore the area

Map
Sarasota, FL
  • Point of Rocks
    ‪5 min walk‬
  • Crescent Beach
    ‪5 min walk‬
  • Siesta Key Beach
    ‪3 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪26 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 Ed Smith Stadium 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

  • Point of Rocks - 5 min walk - 0.4 km
  • Crescent Beach - 5 min walk - 0.5 km
  • Siesta Key Marina - 13 min walk - 1.2 km
  • Siesta Key Beach - 3 min drive - 1.9 km
  • Turtle Beach - 4 min drive - 3.1 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. 99 out of 113 reviews
Rating 8 - Good. 12 out of 113 reviews
Rating 6 - Okay. 2 out of 113 reviews
Rating 4 - Poor. 0 out of 113 reviews
Rating 2 - Terrible. 0 out of 113 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

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

stahlwd@juno.com

Liked: Cleanliness, check-in, communication, location, listing accuracy
Siesta Key Cottage
Our stay was great. It was a short walk to Siesta key with a small pool outside. It had a washer/dryer which alllowed us to pack lighter. The furnishings were very nice. It was my four sons & I including one of my son’s wife & infant daughter. We had a nice time.
Stayed 9 nights in Jan 2025

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

William W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Little get away
This was in a great location. Property was stocked with everything you needed. Dave was supper nice and helpful. Highly recommended checking out the Spear Grill, Jake’s Ice Cream. All within walking distance.
Stayed 4 nights in Sep 2024

10/10 Excellent

Jessica b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place
Such an amazing property! Can tell the care the love and care that goes into the place! Exactly what we were looking for! So grateful we chose Marc’s place!
Stayed 2 nights in Sep 2024

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

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

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

Jeheira A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A Gem in Siesta key!!!
We rented three cottages for our family vacation (14 of us) and had an amazing trip. Perfect spot to be together but still have your own space. Great communication and service. From booking to check in, everything was smooth and easy. The family loved everything! Great location within walking distance to the beach, restaurants, etc. All the beach gear you may need and our own pool. Special thanks to Dave and his team for such great service and hospitality! He went above and beyond! We'll definitely be back!
Stayed 6 nights in Jun 2024

10/10 Excellent

Suzanne G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Grad Trip 2024
We were excited to rent all 4 units as we had multiple families. It was perfect space and location. Dave was awesome! Great response, thoughtful of things we may need or want. Really enjoyed our stay!
Stayed 7 nights in Jun 2024

10/10 Excellent

Maite R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family
My family and I were looking for a plan away from home and this was just the prefect place we had an amazing time and the service was great the owner was very attentive and overall the experience was excellent my family and I are definitely looking forward to return
Stayed 2 nights in May 2024

10/10 Excellent

GINA A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property and service!
Perfect family getaway. We rented 3 cottages. 5 adults in each. The rooms were very clean, cozy and beds comfortable. The pull out in the living room, a full/queen size futton, is more comfortable than a sofa bed (which is what I was expecting). The kitchen is clean and well stocked with everything you need. So are the outside closets (beach chairs, wagon, bikes, balls, etc). The pool and jacuzzi were clean and so were all the patios. Kudos to the cleaning crew! Most importantly, the communication with the property manager, Dave, was exceptional! From the time of booking until even after we left! Would give them 10 stars if that was available. We had an amazing experience and will make this place our Sarasota getaway home.
Stayed 2 nights in May 2024

10/10 Excellent

Kelly S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank You!!
My family and I were in town for my son's wedding on beautiful Siesta Key Beach. From booking to check out Marc and his amazing team, Dave and Amber, made our stay comfortable and perfect! The cottage was bright, cozy and clean and the outdoor space offered the perfect flow from sunshine to shade with beautiful, local foliage all around. The bikes were super fun, the amazing beach was just a short walk away...it was perfect! We will definitely be returning in the future. Thanks for making our stay and my son's special day the best it could be!
Stayed 4 nights in Apr 2024

10/10 Excellent

Mia J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Retreat on the beach!
We had a mix of friends & spouses together for a long weekend and we LOVED our stay! We rented all 4 cottages which had everything we needed. The beach is a very short walk down the street and the cottages have wagons filled with beach supplies like chairs, umbrellas, and beach towels stocked in the cottages. Two attached pools and hot tubs along with a shared courtyard, which was perfect for our group! We had a rental car which we enjoyed having but there’s also a trolley that takes you into town area! Highly recommend and we would love to book again
Stayed 3 nights in Apr 2024

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

Dana A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
little slice if heaven
great property, short walk to beach. property manager Dave very attentive and friendly. I wanted for nothing. would book again!
Stayed 3 nights in Apr 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

Nancy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A good Florida-style getaway
We thoroughly enjoyed our stay here. The property is well laid out: the pools and outdoor space are so pleasant. A little dated. The walk to the beach is a bit farther than we had hoped for, but it's not bad, and the beach cart provided was very helpful. Pros: pool & hot tub, location, bikes Cons: time to update indoor furniture and beach lounge chairs Pros: lovely pool and breezeways, plentiful supply of towels, beach cart, good bikes, welcoming & helpful host
Stayed 5 nights in Mar 2024

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

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

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

Patricia B.

Liked: Check-in, communication, location, listing accuracy
Perfect Location
The cottage was perfect for my stay with my two sisters.We were very comfortable. Easy walk to the beach. Although we did not use them, the rental had bikes and beach equipment. We enjoyed the pool and hot tub each night.The free trolley is only a few blocks away and we used almost every day. The unit is aging and needs some updates. Dave and his daughter were very responsive and made sure we had what we needed. Very quiet neighborhood.
Stayed 3 nights in Jan 2024

10/10 Excellent

Julie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family gathering
This was the perfect place for my family. We had a 4 cottages and we had the best time. The lay out was perfect. We used the fire pits every night. Perfect location to everything we needed. The host Dave was so kind and answered my many questions and was available during our stay if we needed anything. He checked in with me during our visit and I thought he went above and beyond.
Stayed 3 nights in Jan 2024

10/10 Excellent

Stephanie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful week!
Our family (teens, adults, grandparents) had a wonderful week at Siesta Key Crescent cottages. The property manager Dave was amazingly attentive and responded to any question we had throughout the week. We rented two cottages which was more than enough room for our 7 older teens/adults, and the outdoor spaces were phenomenal. We ate meals both indoors and outdoors, walked to the beach daily to spend the day or see the spectacular sunset, enjoyed the pool and hot-tub, and our teen son enjoyed using the outdoor workout equipment. The area has a ton to see and do for both warm and cooler weather days (and a nice road with sidewalk for runners or bikers - we don't normally bike but we greatly enjoyed the complimentary bikes on the property). Highly recommend this place! We hope to be back soon :)
Stayed 6 nights in Dec 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!