Search Cottages in Siesta Key

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (179)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The price is HK$1,638
HK$2,143 total
includes taxes & fees
22 Jun - 23 Jun
The Inn On Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Terrace/patio

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

10.0 out of 10, Exceptional, (4)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is HK$981
HK$2,386 total
includes taxes & fees
22 Jun - 23 Jun
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is HK$1,170
HK$3,952 total
includes taxes & fees
22 Jun - 23 Jun
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor pool

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (75)
"We loved everything about this rental! There are so many fun restaurants and bars within walking distance! There's also the convenience of the trolley stop right across the street for trips into the Village. The pool was nice and the beach was very close. We'd definitely recommend this location and we hope to be back next year!"
The price is HK$777
HK$2,348 total
includes taxes & fees
6 Jul - 7 Jul
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Nook Cottage Across street from beach and Heated Pool
Terrace/patio

Nook Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
Nook Cottage Across street from beach and Heated Pool
Lookout Cottage Across street from Beach and Heated Pool
Terrace/patio

Lookout Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (1)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
Lookout Cottage Across street from Beach and Heated Pool
#3 Small house walking distance to Warm Mineral Spring
Exterior

#3 Small house walking distance to Warm Mineral Spring

8.8 out of 10, Excellent, (5)
"Very clean, had everything i needed !!"
The price is HK$432
HK$1,177 total
includes taxes & fees
22 Jun - 23 Jun
#3 Small house walking distance to Warm Mineral Spring
#4 Charming cottage across of warm mineral springs great for 2 person
Exterior

#4 Charming cottage across of warm mineral springs great for 2 person

8.8 out of 10, Excellent, (5)
"Excellent place for what we was looking for The host was very friendly and always helpful Thank you so much "
The price is HK$389
HK$1,128 total
includes taxes & fees
30 Jun - 1 Jul
#4 Charming cottage across of warm mineral springs great for 2 person
Charming cottage for 2 across warm mineral springs park
Fridge, microwave, stovetop, coffee/tea maker

Charming cottage for 2 across warm mineral springs park

9.0 out of 10, Wonderful, (8)
"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 "
The price is HK$432
HK$1,177 total
includes taxes & fees
1 Jul - 2 Jul
Charming cottage for 2 across warm mineral springs park
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Outdoor dining

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (89)
"Beautiful sunsets and loved walking out to the back patio and onto the beach. Great place for 2 people. "
The price is HK$3,517
HK$6,052 total
includes taxes & fees
22 Jun - 23 Jun
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Terrace/patio

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (55)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is HK$3,909
HK$6,744 total
includes taxes & fees
22 Jun - 23 Jun
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Pool Beach Supplies Outdoor Shower PingPong Table
Fridge, microwave, oven, stovetop

Pool Beach Supplies Outdoor Shower PingPong Table

10.0 out of 10, Exceptional, (6)
"This was a super cute house, the property was just as great. Everything was super clean and nice. We had a wonderful stay!"
The price is HK$2,473
HK$4,942 total
includes taxes & fees
29 Jun - 30 Jun
Pool Beach Supplies Outdoor Shower PingPong Table
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Fridge, microwave, oven, stovetop

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (30)
"Fun stay, great location"
The price is HK$1,177
HK$1,955 total
includes taxes & fees
20 Jun - 21 Jun
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
The "Grouper"
Interior

The "Grouper"

9.6 out of 10, Exceptional, (29)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is HK$777
HK$1,656 total
includes taxes & fees
22 Jun - 23 Jun
The "Grouper"
Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9
TV

Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9

2.0 star property
8.0 out of 10, Very good, (1)
"We have stayed at this property at least 20 times before but always booked through the hotel. The property and location are terrific for what we want from Anna Maria Island. However booking through this agency was more expensive and while it worked out OK, the idea that at this price you can only have one trash bag, two roles of toilet paper, and two dishwasher pods seems a bit extreme and showed a lack of good will we thought."
The price is HK$1,374
HK$3,985 total
includes taxes & fees
6 Jul - 7 Jul
Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Holidaying with your group in Siesta Key is a cinch at The Inn On Siesta Key. With conveniences including a nearby beach and WiFi, you're sure to feel comfortable at this 3.5-star cottage. Flip Flop Cottages is another family-friendly stay where you and your squad can escape the hectic pace of the city. This cottage has a 3-star rating and amenities including a picnic area and a barbecue grill. After checking in and kicking back together in your cosy new digs, it's time to head out and explore the sights. Siesta Key Beach and Lido Beach are popular family-friendly attractions in Siesta Key.
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.