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Featured Cottages in Siesta Key

Across The Street From #1 Beach- w/ Relaxed Cancellation Policy Thru 12/31/2020
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Situated by the ocean, this romantic cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are ...

5/5Exceptional! (124 reviews)
Sweet homecoming for me!

"I grew up just a few blocks from this immaculate beach cottage. We had such a delightful time riding bikes all around the island, golfing, walking the beach. Very romantic and well appointed property. Even though the cottage is right on Beach Road, it is very quiet. Plantation shutters in every room ..."…"

Reviewed on Dec 3, 2020

Across The Street From #1 Beach- w/ Relaxed Cancellation Policy Thru 12/31/2020
The Inn On Siesta Key
3.5 out of 5
515 Beach Road, Siesta Key, FL
The price is $199 per night from Dec 10 to Dec 11

With direct access to the beach, this Siesta Key cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell ...

5/5Exceptional! (66 reviews)

"Friendly staff and very welcoming. Great location and accommodations. This was not our first trip to Siesta Key and it won't be our last."…"

Reviewed on Nov 8, 2020

The Inn On Siesta Key
Heated Pool, Beach and Amenities, 2-3 min Walk
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Situated in Siesta Key, this cottage is within a 5-minute walk of Siesta Key Beach and Crescent Beach. Turtle Beach and Siesta Key Marina are also within 3 mi ...

4.6/5Wonderful! (37 reviews)
Convenient location - owner very responsive

"Close to everything - very convenient Owner was very responsive and accommodating. The AC unit broke during our stay and the owner was unable to get a repairman out in a timely manner for the 100 degree weather. He provided another unit next door that we were able to move to. Things happen - his ..."…"

Reviewed on Aug 25, 2020

Heated Pool, Beach and Amenities, 2-3 min Walk
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NEW Listing- Across From #1 Beach- w/ Relaxed Cancellation Policy Thru 12/31/20
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Situated by the ocean, this romantic cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are ...

5/5Exceptional! (26 reviews)
Perfect!

"We loved this cottage! The renovation was so nicely done with a great beachy vibe and comfortable furniture. The area is busy but the cottage is very quiet and in a perfect location; across from the beach and short walk to village. Couldn't have asked for better. We'll be back."…"

Reviewed on Nov 30, 2020

NEW Listing- Across From #1 Beach- w/ Relaxed Cancellation Policy Thru 12/31/20
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
The price is $158 per night from Dec 24 to Dec 25

Situated by the ocean, this cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are also within ...

4.4/5Wonderful! (9 reviews)
"COVID 2020" What a awesome Week!!!!

"We have a awesome time even with the growing concerns of covid 19!! We all got to enjoy a wonderful time and weather before they shut everything down!! Look forward to next year!!"…"

Reviewed on Apr 6, 2020

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Cleaned to new Standards: Two Beautiful Cottages Side By Side - Private Pool
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Situated by the ocean, this romantic cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are ...

4.9/5Exceptional! (23 reviews)
Relaxing getaway

"We had a great time in Siesta Keys. The cottages were well maintained and clean. The location was perfect, close to the beach and downtown. The street is quiet. The pool and hot tub were great. Cheryl thought of everything to be included. The beach carts, umbrellas and chairs made trips to the beach ..."…"

Reviewed on Nov 22, 2020

Cleaned to new Standards: Two Beautiful Cottages Side By Side - Private Pool
Cleaned to new Standards: Gorgeous Cottages Steps From Beach/heated Pool
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Situated by the ocean, this historic cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are ...

5/5Exceptional! (61 reviews)
Our stay at Sea Palm Cottages

"Whenever we can, we stay at The Sea Palm Cottages. They are extremely clean with all of the comforts of home. Cheryl, the owner can’t do enough to make our stay the best ever! We love it here! We’ll be back soon! Al and Brenda Peters"…"

Reviewed on Oct 7, 2020

Cleaned to new Standards: Gorgeous Cottages Steps From Beach/heated Pool
Cheap!!- Monthly Rental Only - Siesta Key , Florida
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Situated on the waterfront, this cottage is within 1 mi (2 km) of Irma Beach and Siesta Key Beach. Shell Beach and Bay Island are also within 3 mi (5 km).

5/5Exceptional! (3 reviews)
Amazing rental

"We have been staying at this amazing place for four years. You cannot beat the location and the views, the gulf from the living room and the deck. It is a short walk to the private beach with a fishing pier, and a 5-10 minute stroll to the Village for shopping and dining. The owners are so accommodating ..."…"

Reviewed on Apr 3, 2019

Cheap!!- Monthly Rental Only - Siesta Key , Florida
Crescent Beach Side - Clean, Cozy & Convenient!
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Situated by the ocean, this cottage is within a 5-minute walk of Crescent Beach and Siesta Key Beach. Turtle Beach and Siesta Key Marina are also within 3 mi ...

4.6/5Wonderful! (20 reviews)
Great rental!

"Second time staying here. Perfect location. Perfect place for a couple or small family. Minutes from great food options, bars, live music, ice cream and of course the beautiful beaches. Enjoyed the stay thoroughly. Owners great with communication. Everything needed for the beach ptovided. Love this ..."…"

Reviewed on Oct 29, 2020

Crescent Beach Side - Clean, Cozy & Convenient!
Incredible Cottage in Paradise Walk to the Beach or Village - Very Convenient
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Situated in Siesta Key, this romantic cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are ...

4.5/5Wonderful! (2 reviews)
Beautiful and convenient to all the island amenities.

"My wife and I loved this rental. It was absolutely perfect for our needs and gave us direct access to Siesta Beach and the village. Clean, comfortable and private. We will be staying at this property again if possible."…"

Reviewed on Sep 8, 2020

Incredible Cottage in Paradise Walk to the Beach or Village - Very Convenient
Sea Club II Cottages by Beachside Mgt
3 out of 5
5955 Midnight Pass Road, Siesta Key, FL
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Offering direct access to the beach, this Siesta Key cottage is within a 15-minute walk of Siesta Key Beach and Crescent Beach. Siesta Key Marina is 1.1 mi (1.8 ...

3.7/5Good! (10 reviews)

"The property is comfortable and quaint -- sort of like Siesta Key back in the day. The amenities are very good, the screen porch is delightful, and the trees make it cool. Pool is great, benches on the ICW, and access to beach across the street."…"

Reviewed on May 28, 2019

Sea Club II Cottages by Beachside Mgt
Flip Flop Cottages
3 out of 5
8254 Midnight Pass Road, Siesta Key, FL
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Situated in Siesta Key, this cottage is within 2 mi (3 km) of Turtle Beach, Siesta Key Beach, and Crescent Beach. Siesta Key Marina is 1.9 mi (3 km) away.

3.8/5Good! (6 reviews)
Cute and charming

"Very cute. Pool was a bit small"…"

Reviewed on Jul 7, 2017

Flip Flop Cottages
Cleaned to New Standards: Gorgeous Cottage Steps From Beach
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Situated in Siesta Key, this cottage is within 3 mi (5 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Irma Beach and Shell Beach are also within ...

4.9/5Exceptional! (50 reviews)
Siesta cottage

"Wonderful cottage. Great area and 1 block from the beach and walkable to Siesta Village ships and restaurants. Everything you need for a getaway to the beach. Owner excellent to work with and available if needed. We thoroughly enjoyed our time"…"

Reviewed on Aug 1, 2020

Cleaned to New Standards: Gorgeous Cottage Steps From Beach
Foxtail Cottage 1 Bedroom 1 Bathroom Cottage
3.5 out of 5
1032 Point of Rocks Rd, Siesta Key, FL
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Situated in Siesta Key, this cottage is within a 5-minute walk of Siesta Key Beach and Crescent Beach. Turtle Beach and Siesta Key Marina are also within 3 mi ...

Foxtail Cottage 1 Bedroom 1 Bathroom Cottage
Sea Club II Cottages On the Bay
3 out of 5
5955 Midnight Pass Rd, Siesta Key, FL
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Situated in Siesta Key, this beach cottage is within a 15-minute walk of Siesta Key Beach and Crescent Beach. Siesta Key Marina is 1.1 mi (1.7 km) away.

5/5Exceptional! (1 review)
Little piece of paradise

"I would highly recommend this place, I would love to come back some day. If you ever get a chance to get this place grab it. Thank you Sea Club!!! 😍😎🌴🌴"…"

Reviewed on Jun 29, 2019

Sea Club II Cottages On the Bay
Sea Club II Unit 3A Bayside Unit With Beach Access! 1 Bedroom 1 Bathroom Cottage
3.5 out of 5
5955 Midnight Pass Rd, Unit 3-A, Siesta Key, FL
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Situated near the bay, this cottage is within 2 mi (3 km) of Siesta Key Beach, Crescent Beach, and Siesta Key Marina. Point of Rocks and Irma Beach are also ...

Sea Club II Unit 3A Bayside Unit With Beach Access! 1 Bedroom 1 Bathroom Cottage
Siesta Beach House C, Minute Walk To Beach 3 Bedroom Apts
3 out of 5
5950 Midnight Pass Rd, Unit C, Siesta Key, FL
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Situated near the beach, this cottage is within a 15-minute walk of Siesta Key Beach and Crescent Beach. Siesta Key Marina is 1.1 mi (1.8 km) away.

Siesta Beach House C, Minute Walk To Beach 3 Bedroom Apts
436 Avenida de Mayo-private Village Location 3 Bedrooms 2 Bathrooms Home
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Located in Siesta Key Village, this cottage is within 1 mi (2 km) of Irma Beach and Siesta Key Beach. Crescent Beach and Siesta Key Marina are also within 3 ...

436 Avenida de Mayo-private Village Location 3 Bedrooms 2 Bathrooms Home
White Wood Cottage 1 Bedroom 1 Bathroom Cabin
3.5 out of 5
1131 Point of Rocks Rd, Siesta Key, FL
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Situated in Siesta Key, this cottage is within a 5-minute walk of Siesta Key Beach and Crescent Beach. Turtle Beach and Siesta Key Marina are also within 3 mi ...

White Wood Cottage 1 Bedroom 1 Bathroom Cabin
Blue Sage Cottage 1 Bedroom 1 Bathroom Cottage
3.5 out of 5
1131 Point of Rocks Rd, Siesta Key, FL
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Situated in Siesta Key, this cottage is within a 5-minute walk of Siesta Key Beach and Crescent Beach. Turtle Beach and Siesta Key Marina are also within 3 mi ...

Blue Sage Cottage 1 Bedroom 1 Bathroom Cottage
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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.

Other property types in Siesta Key

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
The price is $95 per night from Dec 6 to Dec 7
4.6/5Wonderful! (2,446 reviews)

"Everything was good. Very limited and not always convenient parking. Interior of room was somewhat worn but clean."…"

Reviewed on Nov 25, 2020

Tropical Beach Resorts
The Conclare Beach Resort

The Conclare Beach Resort

3 out of 5
6738 Sarasea Cir, Siesta Key, FL
The price is $87 per night from Dec 6 to Dec 7
4.5/5Wonderful! (57 reviews)

"Excellent low-key property, perfect for families. The beach is one only one minute away."…"

Reviewed on Dec 2, 2020

The Conclare Beach Resort
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
The price is $105 per night from Dec 6 to Dec 7
4.2/5Very Good! (986 reviews)

"This was a great location and nice units! Everything is within in walking distance! Great for families"…"

Reviewed on Nov 29, 2020

Tropical Breeze Resort
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.