Search Cottages in Siesta Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Cottages in Siesta Key and around

The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio
The Inn On Siesta Key
The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (188)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is €287
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is €278
includes taxes & fees
10 Nov - 11 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (176)
"clean, nice amenities and great location"
United States
Robert K.
The price is €363
includes taxes & fees
11 Nov - 12 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Pool
Nest Cottage Across street from beach and Heated Pool
Nest Cottage Across street from beach and Heated Pool
10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is €494
includes taxes & fees
19 Nov - 20 Nov
Nest Cottage Across street from beach and Heated Pool
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage
7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (2)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is €244
includes taxes & fees
11 Nov - 12 Nov
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
#3 Small house walking distance to Warm Mineral Spring
#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (8)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is €139
includes taxes & fees
7 Nov - 8 Nov
#3 Small house walking distance to Warm Mineral Spring
Exterior
Charming cottage for 2 across warm mineral springs park
Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"I'm currently working in the area and this place made it even easier being away from home I've enjoyed the area and the place "
United States
Andy B.
The price is €139
includes taxes & fees
7 Nov - 8 Nov
Charming cottage for 2 across warm mineral springs park
Exterior
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
9.2 out of 10, Wonderful, (67)
"We so enjoy this little property loved the beach and it’s coziness would definitely refer ones to it and would stay again found lots of shells and sharks teeth"
United States
Bobbie H.
The price is €427
includes taxes & fees
9 Nov - 10 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Outdoor dining
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
2.0 star property
The price is €152
includes taxes & fees
1 Dec - 2 Dec
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Exterior
Romantic Island Getaway! Just Steps from the Beach
Romantic Island Getaway! Just Steps from the Beach
2.0 star property
8.8 out of 10, Excellent, (3)
"Although there are laundry facilities on property, the area is kept locked and this unit is not permitted access. We were unable to do any laundry unless we traveled two miles to Holmes Beach to the Laundromat. This property IS very quiet. The trolley stops are literally at the end of the driveway, but there are no shops or businesses within close walking distance. Also, there were beach chairs and towels, but THERE ARE NO EXTRAS here, which is unlike any other Vrbo/AirBnb we have visited. There...
United States
Amy
The price is €335
includes taxes & fees
11 Nov - 12 Nov
Romantic Island Getaway! Just Steps from the Beach
Exterior
The "Grouper"
The "Grouper"
9.2 out of 10, Wonderful, (40)
"Very clean and nice place ."
United States
Sherry S.
The price is €190
includes taxes & fees
12 Nov - 13 Nov
The "Grouper"
Exterior
Gulf Gate Escape near Siesta Key
Gulf Gate Escape near Siesta Key
2.0 star property
The price is €314
includes taxes & fees
6 Dec - 7 Dec
Gulf Gate Escape near Siesta Key
Terrace/patio
5 star Guest House heated pool on the water!
5 star Guest House heated pool on the water!
The price is €453
includes taxes & fees
7 Nov - 8 Nov
5 star Guest House heated pool on the water!
Outdoor dining
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
9.4 out of 10, Exceptional, (103)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
The price is €404
includes taxes & fees
8 Nov - 9 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siesta Key Hotel Reviews

Siesta Key Beachside Villas

Siesta Key Beachside Villas

10/10 Excellent
"Cute little villa in the middle of everything. Easy access to the beach with carts and bikes available. Everios within walking distance which made it easy to get around and not having to worry about driving and parking. The villas are cozy and had everything we needed including a cooler bag, ice and beach chairs and towels. I would recommend this place and will look to return again. "
Joshua 3-night trip
Posted 12 hours ago
Siesta Key Beachside Villas

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
454
Accommodation
32 Cottages
Lowest Price
€152
Highest Price
€494

Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Many visitors needing a family-friendly cottage in Siesta Key choose The Inn On Siesta Key. With a 3.5-star rating and amenities including a nearby beach and laundry facilities, it'll feel like your home away from home. Another great option for holidaying families is Flip Flop Cottages. Laundry facilities and a barbecue grill help make this 3-star cottage a comfortable base for your Siesta Key trip. Siesta Key has lots of family-friendly attractions to visit that'll entertain the kids. Siesta Key Beach and Lido Beach promise a fun-fuelled day for travellers both young and old.
Why book your cottage in Siesta Key with Expedia?
Booking a cottage in Siesta Key is as easy as entering your travel dates and picking your ideal place for a holiday in the outdoors. From upscale retreats to inexpensive stays and cottages that offer perks like a pool, Expedia has something for all styles. As for terrific deals? We have them too!
How can I find cheap cottages in Siesta Key?
The simplest way to score cheap cottages in Siesta Key is with Expedia's user-friendly filter tool. Narrow down your search by star rating, budget and amenities to grab awesome rates with only a few clicks.

Explore a world of travel with Expedia