Search Siesta Key Cottages

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Cottages in Siesta Key

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
Siesta Key
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
$268 nightly
The price is $303
Nov 11 - Nov 12
Total with taxes and fees
The Inn On Siesta Key
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key
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.
$305 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
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

Sarasota
9.2 out of 10, Wonderful, (176)
"clean, nice amenities and great location"
United States
Robert K.
$357 nightly
The price is $398
Nov 11 - Nov 12
Total with taxes and fees
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

Siesta Key
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.
$481 nightly
The price is $536
Nov 19 - Nov 20
Total with taxes and fees
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

Bradenton
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.
$246 nightly
The price is $274
Nov 11 - Nov 12
Total with taxes and fees
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

Warm Mineral Springs
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.
$140 nightly
The price is $156
Nov 9 - Nov 10
Total with taxes and fees
#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

Warm Mineral Springs
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.
$140 nightly
The price is $156
Nov 9 - Nov 10
Total with taxes and fees
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

Casey Key
9.2 out of 10, Wonderful, (68)
"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.
$429 nightly
The price is $478
Nov 9 - Nov 10
Total with taxes and fees
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
Nokomis
$148 nightly
The price is $165
Dec 1 - Dec 2
Total with taxes and fees
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
Bradenton Beach
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
$337 nightly
The price is $375
Nov 11 - Nov 12
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach
Exterior
The "Grouper"

The "Grouper"

Sunny Shores
9.2 out of 10, Wonderful, (40)
"Very clean and nice place ."
United States
Sherry S.
$191 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
The "Grouper"
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

2.0 star property
Sarasota
$319 nightly
The price is $356
Dec 4 - Dec 5
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

South Sarasota
$456 nightly
The price is $508
Nov 9 - Nov 10
Total with taxes and fees
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

Casey Key
9.4 out of 10, Exceptional, (104)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
$406 nightly
The price is $453
Nov 9 - Nov 10
Total with taxes and fees
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 Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"The room was wonderful , the Staff were very friendly and helpful . It's a great place ! "
Thomas 2-night trip
Posted 4 days ago
Siesta Key Beach Resort and Suites

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

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 vacationing 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-fueled day for travelers 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 vacation 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