Search Siesta Key Cottage Rentals from CA $206

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Siesta Key cottages

Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $226
CA $511 total
includes taxes & fees
Apr 20 - Apr 21
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is CA $354
CA $1,047 total
includes taxes & fees
Apr 20 - Apr 21
Blue Dolphin Cottage steps from the beach
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key
Exterior

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is CA $136
CA $416 total
includes taxes & fees
Apr 28 - Apr 29
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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, (181 reviews)
"Very close to the village and we only had to cross the road to access the beach!! Loved it!!"
United States
Kim H.
The price is CA $385
CA $701 total
includes taxes & fees
May 10 - May 11
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is CA $373
CA $1,072 total
includes taxes & fees
Apr 20 - Apr 21
Yellow Palm Cottage steps from the beach
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is CA $373
CA $1,072 total
includes taxes & fees
Apr 20 - Apr 21
Pink Mango Cottage steps from the beach
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $862
CA $1,389 total
includes taxes & fees
Apr 29 - Apr 30
Siesta Heron 6 / Sunset
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
The price is CA $1,069
CA $1,472 total
includes taxes & fees
May 10 - May 11
Beach Road
Outdoor dining

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is CA $951
CA $1,655 total
includes taxes & fees
Apr 27 - Apr 28
Siesta Heron 7
Interior

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
Stylish Retro Vibes Private BBQ & Beach Access
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is CA $341
CA $750 total
includes taxes & fees
Apr 20 - Apr 21
Direct Beachfront 2BR Cottage on Casey Key!
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (58 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is CA $136
CA $293 total
includes taxes & fees
Apr 26 - Apr 27
The "Grouper"
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (6 reviews)
"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 CA $105
CA $374 total
includes taxes & fees
Apr 17 - Apr 18
Coastal Luxury 7mi to Anna Maria Private Cottage
Property grounds

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is CA $255
CA $820 total
includes taxes & fees
Apr 20 - Apr 21
Romantic Island Getaway! Just Steps from the Beach
Exterior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is CA $76
CA $206 total
includes taxes & fees
May 14 - May 15
Charming cottage for 2 across warm mineral springs park
Exterior

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.8 out of 10, Excellent, (3 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is CA $209
CA $486 total
includes taxes & fees
May 7 - May 8
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Property grounds

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (124 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is CA $434
CA $929 total
includes taxes & fees
May 4 - May 5
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is CA $179
CA $622 total
includes taxes & fees
Apr 23 - Apr 24
Lido Key Getaway - Bikes & Beach Gear
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (118 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveller
The price is CA $410
CA $803 total
includes taxes & fees
Apr 27 - Apr 28
Casey Key Beachfront Escape: Charming 1BR Cottage
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.
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Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Parking was very tricky, but worked out fine. It’s a lovely well care for resort resort. Don’t have a single complaint about it… The pool area was a gorgeous jungle and the beach was beautiful and the room was excellent."
Helen 1-night trip
Posted 4 hours ago
Tropical Beach Resorts

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
694
Accommodation
54 Cottages
Lowest Price
CA $206
Highest Price
CA $1,655

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-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 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?
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