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Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

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Tucked beneath the palms—your private oasis awaits with a sparkling pool just steps from the shore.
Steps from Crescent Beach and moments to Siesta Key Village—welcome to your island escape.
Surrounded by swaying palms and coastal charm—Topsail Cottage is your private slice of paradise.
Fire up the grill, pour a cold drink, and settle into the breeze—this balcony was made for sunset dinners and slow, golden afternoons.
Unwind in spa-like serenity—a deep soaking tub, walk-in shower, and calming tones create a private retreat made for total relaxation in bedroom 2's ensuite.

Reviews

9.8 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 123349 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Rooms & beds

4 bedrooms (sleeps 12)

Bedroom 1

1 King Bed and 1 Double Sofa Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed and 1 Double Sofa Bed

Bedroom 4

1 King Bed

Common Space

1 Double Sofa Bed

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Kitchen
Kitchenette
Balcony
Separate dining area
Dining area

About this property

Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

🌴 Topsail Cottage | Gulf Views + Walk to Crescent Beach

💖 Why You'll Love This Home
Wake up to sea breezes and panoramic Gulf views from your private rooftop crow's nest. Topsail Cottage is a luxury beach retreat where indoor-outdoor living, four private king suites, and designer touches create the perfect coastal escape.

👨‍👩‍👧 Perfect For
Couples, multi-gen families, or small groups looking for a walkable Siesta Key location with upscale amenities and beach gear included.

🎞️ Imagine This
You arrive, step inside, and feel the soft coastal breeze drift through the open living space. Your family gathers in the sunlit kitchen, laughing over fresh drinks while dinner simmers nearby. Upstairs, the rooftop crow's nest draws you up with a glass of wine in hand—where Gulf waters glisten in every direction. Later, the kids splash in the heated pool while you prep dinner on the outdoor grill station. As the sun dips below the palm trees, you realize: this is exactly how vacation should feel.

🛌 Where You'll Sleep
- Bedroom 1: King Bed + Twin Chair Sleeper, Ensuite Bath, Main Floor, TV
- Bedroom 2: King Bed, Ensuite Bath, Second Floor, TV
- Bedroom 3: King Bed, Ensuite Bath, Second Floor, TV
- Bedroom 4: King Bed + Twin Chair Sleeper, Ensuite Bath, Second Floor, TV
- Living Area: Queen Sleeper Sofa, TV

📍 Explore the Area
- 0.2 miles from Crescent Beach
- Short Drive or Bike to Siesta Key Village and South Siesta's Dining and Shops

⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection, so you arrive at a pristine, hotel-quality home every time.

🔎 Need To Know: This home is located in an HOA with a shared pool. This pool is heated from November 15th to April 15th. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

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Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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  • Kitchen
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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
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

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 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 in the city centre and 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Sarasota, FL

What's nearby

  • Crescent Beach - 5 min walk - 0.4 km
  • Siesta Key Marina - 11 min walk - 1.0 km
  • Siesta Key Beach - 18 min walk - 1.6 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.) - 41 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Culver's - ‬4 min drive
  • ‪Hooters - ‬4 min drive
  • ‪Five Guys - ‬4 min drive
  • ‪Taco Jalisco - ‬4 min drive

Frequently asked questions

Does Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach! have a pool?

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

How much does it cost to stay at Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!?

As of 12 Mar, 2026, prices found for a 1-night stay for 2 adults at Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach! on 30 May, 2026 start from S$1,029, 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 Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!?

On-site parking is available at the property.

What time is check-in at Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!?

Check-in begins at 4:00 PM.

What time is check-out at Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!?

Checkout is at 10:00 AM.

Where is Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach! located?

Located in the heart of Siesta Key, this holiday home is within a 5-minute walk of Point of Rocks and Crescent Beach. Siesta Key Beach and Turtle Beach are also within 3 miles (5 km).

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. 36 out of 41 reviews
Rating 8 - Good. 4 out of 41 reviews
Rating 6 - Okay. 0 out of 41 reviews
Rating 4 - Poor. 1 out of 41 reviews
Rating 2 - Terrible. 0 out of 41 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Joel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay here. This cottage was beautiful - very clean and spacious. The staff were very responsive, and got back to us normally within minutes about any request. Best of all, it was about a 5 minute walk to the beach! I would 100% stay again, as we all absolutely loved it!
Stayed 7 nights in May 2025

10/10 Excellent

Sharon A.

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

Beautiful home great neighborhood!

Home was simply amazing, clean and comfortable. Definitely will consider again next trip!
Stayed 4 nights in Feb 2025

10/10 Excellent

Julianne I.

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

Topsail stay

Had a fabulous time -the house is amazing!
Stayed 4 nights in Oct 2019

10/10 Excellent

Patricia K.

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

Perfect location for a family beach vacation!

This property was perfect for our multi-generational family gathering of 9! Easy walk over to Cresent Beach with no busy roads to cross. The kitchen was large with plenty of dishes, silverware and cooking/baking equipment.
Stayed 7 nights in Dec 2024

10/10 Excellent

Kami S.

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

Such a great stay

This VRBO was amazing! The house was beautiful, the supplies toiletries were great, and they even had a treat for us upon arrival. This house is so beautiful and close to the beach, shops, and restaurants. We also had the pool to ourselves through the week which was nice. The beach wagon/buggy that was supplied was also so helpful.
Stayed 7 nights in Jun 2023

10/10 Excellent

Verified traveller

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

Topsail cottage

Beautiful home. Great location. We came to the area for a high school baseball tournament and so glad we chose to stay at Siesta Key. The beach was amazing. The home had everything we needed for the beach. The kids also enjoyed the pool.
Stayed 8 nights in Jul 2023

10/10 Excellent

Rosemarie C.

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

Paradise

Beautiful house, perfect location. This house has everything you could possibly need and some...things you would never imagine. Just perfect!
Stayed 5 nights in May 2024

10/10 Excellent

JoAnne P.

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

Perfect privacy

Plenty of sleeping spaces. Fully equipped kitchen, great beach and beach accessories. Great location for walking to nearby establishments. Only negative was the bbq grill not having even heat. Would definitely consider this property again.
Stayed 7 nights in Feb 2024

10/10 Excellent

Mary H.

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

Beautiful Home - Great for Families / Groups!

Our group of 7 loved this house. All bedrooms have walk-in closets & full baths, so everyone had plenty of space. The kitchen is large and well stocked. The covered porch w/ outdoor kitchen is amazing - we spent lots of time there!! The pool is small but nice, and the ocean is about a 5 minute walk. We loved it!
Stayed 21 nights in Jan 2023

10/10 Excellent

Debra W.

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

Highly recommend!!!

Great property, location, this house has it all. 9 of us and we were all so very comfortable. The pool was awesome and the house was super clean. We enjoyed every minute. The Beach is just a short walk away with a beautiful sunset. Would definitely return!!!
Stayed 6 nights in May 2023

10/10 Excellent

Brenda J C.

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

Siesta Key 2021

We have stayed in several houses on the Key and other locations. This house was by far the nicest. There was plenty of room for the nine of us. The property and pool were well maintained. The kitchen had everything we needed and there was plenty of linens. A great house-thank you so much.
Stayed 7 nights in Apr 2021

10/10 Excellent

Luanne J.

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

1025 Crescent was very nice!

Great property and great location. Thanks for the custom cupcakes upon arrival! The only glitch was that the prior renters took the pool gate key/garage door openers with them, so we didn't get to use the pool as much as we would have liked. Otherwise, it was a wonderful stay!
Stayed 7 nights in Jan 2023

10/10 Excellent

Nestor M.

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

Home Away from Home

Coming to the Cottages for a much needed family get away before the school season and this was the escape we needed. The sheer size and amount of space to "live" in for the week was overwhelming. Truly a welcome experience. All the bedrooms had a private bathroom, the pool was essentially ours for the week, and the beach was right around the corner. I had such a chill time, I never made it to the downtown area, except to go the the market. Highly recommend a stay. Bonus fact: we needed an air fryer and we received an air fryer. Simply magic.
Stayed 8 nights in Jul 2022

10/10 Excellent

David C.

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

Fantastic Property

TopSail exceeded our expectations! I don't think the online pictures do it justice. House was beautiful and well laid out. It was extremely spacious and enabled our family of 8 to spread out. Great kitchen / dining area. Loved the semi-private pool and short walk to the beach. Felt very safe allowing our youngest (9) to walk back to the house from the beach. We used just about all of the 'extras' in the garage - bikes, beach chairs, coolers, etc. The 'rooftop' balcony is a little difficult to access up the narrow spiral staircase, but the view is worth the effort. I would highly recommend this property.
Stayed 7 nights in Mar 2021

8/10 Good

Jacqueline P.

A wonderful place for a family gathering

We thoroughly enjoyed our stay at Topsail Cottage. Even though our numbers ebbed and flowed, at one point reaching eleven people, we never felt crowded as the house is huge. The beach, restaurants and stores are close enough to walk easily. The pool area was wonderful. Having the cabana with bathrooms and a shower right by the pool was amazing. Very usual especially when you have young children spending hours in the pool. The elevator was great when unloading suitcases and groceries. We did have a few issues but they were resolved so quickly and painlessly that you hardly knew anything was amiss. All the people we delt with were polite and helpful. Especially Chris when he came over to hand deliver a bottle of wine!! Thanks again for a lovely two weeks.
Stayed 14 nights in Apr 2018

10/10 Excellent

Mark R.

Beautiful Property and Fantastic Amenities 5-Stars

Had a fantastic time and this property is worthy of a 5 Star rating. First, the place is huge, everything from all living and dining areas to the closets and bathrooms are very large. Has every amenity from seeing the bicycles when you first drive in the garage to having your own pool with its own cabana. (2 bathrooms, kitchen with dining table) The best part for us, my wife uses a walker and the elevator could get her to all 3 levels with no problems. The staff was spot on, checking in to make sure all was good. Of course the wonderful cupcakes sitting in the fridge made our arrival extra special. Entrance to beach is only a few houses away, no need to drive anywhere. If we come back to town, for sure we would stay there again. I cannot think of one negative I could even say.

10/10 Excellent

Ricardo T.

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

Great property!!!

The property is as great as pictures described! Very close to beach access (3-5min walk) and the sea is AMAZING!! Warm, calm and clear water!! I don’t know how busy the swing pool can get but we had it for ourselves only for almost all the time just met 3 ppl there one day. Elevator was super helpful for elderly and to move bags up and down, otherwise we didn’t mind using the stairs! Overall a super nice experience and a super nice property!!! Just be aware that the beach access closest to the house you can’t park but the house is close enough to walk back after dropping your cooler/beach stuff! We rented a golf cart and used for this purpose but someone would drive it back to the house because couldn’t park it, which was not even an inconvenience for us! 5stars all the way!!
Stayed 6 nights in Jun 2023

10/10 Excellent

DAVID A.

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

Siesta Key

Great property with a short walk to the beach.
Stayed 7 nights in Apr 2022

10/10 Excellent

Joseph J.

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

Great House for large group

The house was great and accurately fit the description and photos. It was awesome that each bedroom had it's own full bathroom and large walk in closet. Pool area in back was very convenient and the beach is a short couple minute walk.
Stayed 7 nights in Apr 2022

10/10 Excellent

AMANDA N.

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

Amazing Vacation Home

We absolutely loved our stay here! Everything was clean and the house was well stocked. The beds were extremely comfortable. The beach was a short walk and they provided beach towels, chairs, cooler, caddy, and umbrella. We had the best time! They left cupcakes for our family bc we were celebrating a birthday while we were there. Best service! Highly recommend staying here.
Stayed 7 nights in Mar 2022

8/10 Good

Chris B.

Liked: Check-in, communication, location

Attention to detail is missing

Location was good. The shared pool was ok but the pool house was off limits to guests. Would have been nice to know
Stayed 7 nights in Mar 2022

10/10 Excellent

Rose M.

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

Beautiful property

There were 4 adults and 4 adult children. This property accommodated us perfectly. There was enough seating for all of us when we were all exhausted from a day of fun! We didn’t use the outside patio as much as I thought due to the humidity. We did use the pool everyday. Basically 1 block to the beach. I highly recommend Topsail 5!
Stayed 8 nights in Sep 2021

10/10 Excellent

Whitney M.

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

Fantastic!

We loved this property and all the amenities that came with it! The house is beautiful and the elevator came in handy way more than we anticipated. Would love to come back and stay again!
Stayed 7 nights in Aug 2021

4/10 Poor

JILL P.

Liked: Check-in, communication
Disliked: Cleanliness

July stay 2021

Nice spacious, house but floors were filthy and so were walls, windows and some of the leather furniture. The washing machine was also dirty. The kitchen is missing dishware and lacked large serving bowls and had a lot of mis matched aged dishes, containers, silverware and glasses. The pool was a huge let down it seems older than it is, small, dirty and not inviting.
Stayed 7 nights in Jul 2021

10/10 Excellent

Jan S.

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

Family vacation before 2 high school graduates go off to college!!

This was the perfect house for a family vacation with adults & 5 teenagers! They enjoyed walking or biking to nearby shops & restaurants! Unfortunately there wasn’t a whole lot of beach space!
Stayed 7 nights in Jun 2021

About the host

Hosted by The Cottages on the Key, Inc.

Host profile image

What makes this property unique

Welcome to Topsail Cottage, one of Siesta Key’s most luxurious vacation rental homes, with private heated pool and private elevator. Enjoy breathtaking views on your very own rooftop deck that features a gorgeous spiral staircase. This home is ideal

Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests
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