Featured Cottages in Siesta Key

Estimated price for 1 night/2 adults

The Inn On Siesta Key
The Inn On Siesta Key
3.5 out of 5.0 515 Beach Road, Siesta Key, FL
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5.0/5 (80 reviews)

Loved our stay ... Place was spotless...short walk to a beautiful beach and the heated pool when the sun went down was a huge plus.... highly recommended

Reviewed on Jan 9, 2021
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 ...
Flip Flop Cottages
Flip Flop Cottages
3.0 out of 5.0 8254 Midnight Pass Road, Siesta Key, FL
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3.8/5 (6 reviews)

Very cute. Pool was a bit small

Reviewed on Jul 7, 2017
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.
315 Canal Rd- Awesome Village Location! 2 Bedroom Apts
315 Canal Rd- Awesome Village Location! 2 Bedroom Apts
3.0 out of 5.0 315 Canal Rd, #315, Siesta Key, FL
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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 ...
309 Canal Rd-awesome Village Location! 2 Bedroom Apts
309 Canal Rd-awesome Village Location! 2 Bedroom Apts
3.0 out of 5.0 309 Canal Rd, #81148, Siesta Key, FL
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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 ...
Aloha Kai - Unit 14a-close To Beach And Pool! 1 Bedroom Apts
Aloha Kai - Unit 14a-close To Beach And Pool! 1 Bedroom Apts
3.0 out of 5.0 6020 Midnight Pass Rd, # 14A, Siesta Key, FL
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Located in Aloha Kai, 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.
436 Avenida de Mayo-private Village Location 3 Bedrooms 2 Bathrooms Home
436 Avenida de Mayo-private Village Location 3 Bedrooms 2 Bathrooms Home
3.0 out of 5.0 436 Avenida De Mayo, Siesta Key, FL
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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 ...
Wild Plum Cottage Studio Bedroom 1 Bathroom Cottage
Wild Plum Cottage Studio Bedroom 1 Bathroom Cottage
3.5 out of 5.0 1035 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 ...
Sea Club II Cottages On the Bay
Sea Club II Cottages On the Bay
3.0 out of 5.0 5955 Midnight Pass Rd, Siesta Key, FL
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5.0/5 (1 reviews)

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
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.
White Wood Cottage 1 Bedroom 1 Bathroom Cabin
White Wood Cottage 1 Bedroom 1 Bathroom Cabin
3.5 out of 5.0 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 ...
Foxtail Cottage 1 Bedroom 1 Bathroom Cottage
Foxtail Cottage 1 Bedroom 1 Bathroom Cottage
3.5 out of 5.0 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 ...
Sea Club II Cottages by Beachside Mgt
Sea Club II Cottages by Beachside Mgt
3.0 out of 5.0 5955 Midnight Pass Road, Siesta Key, FL
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3.7/5 (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
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 ...
Siesta Beach House C, Minute Walk To Beach 3 Bedroom Apts
Siesta Beach House C, Minute Walk To Beach 3 Bedroom Apts
3.0 out of 5.0 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.

Alternative Accommodations - Cottages

Cottage rentals in Siesta Key

Looking to get away and find your own cozy little nook out of town? If you’re craving a home-away-from-home feeling on your next vacation, cottage rentals are the perfect answer to the call. Maybe you’ve been dreaming of warming yourself by a fire at lake cottage rentals or sorting through your beachcombing seashell haul at cottages for rent on the beach. Anything’s possible when you book weekend cottage rentals through AARP Travel.

 

Can you rent a cottage in Siesta Key?

Cottages for rent in Siesta Key can offer many of the amenities of home with the added benefit of being able to explore brand-new surroundings. You can wake up in your weekend abode with everything you need to get comfy and relax to the max. From sweet and simple to sprawling, you’ll find cottages to rent in all sizes and levels of luxury. Whether you’re just looking for an eat-in kitchen with easy access to a wine opener or want to book a cottage rental with a spacious balcony and vast views, there are cottages for rent in Siesta Key to fit the bill.

Unwinding in your cottage rental after a day of taking in the sights of Siesta Key is a breeze. With all the privacy and tranquility you need to relax, you can forget it all and take it easy in your own space with a glass of wine or a steaming mug of coffee. The bottom line? A cottage getaway in Siesta Key is a great low-stress way to explore the area while still having every comfort at your fingertips. 

 

How to find a cottage rental in Siesta Key

Taking in all Siesta Key has to offer in the coziest way is simple. When you book cottage getaways in Siesta Key using the AARP Travel Center Powered by Expedia, you can count on getting not just members-only discounts, but also the greatest deals from Expedia. No matter if you’re looking for beach cottages, lake cottages, or even rustic cottages brimming with charm, booking your stay through AARP Travel gets you the best rates around.

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Estimated price for 1 night/2 adults

Tropical Beach Resorts

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