Cottages Siesta Key

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69 cottages

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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$171

Beach Place - Seahorse Cottage - Peak of the Gulf, 30 Seconds to the Sand

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 42 minutes

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$161

Walk to Beach, Fully Renovated with Highend Finishings, Wifi/Cable, Heated Pool,

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

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$134

Cute 2Bedroom/1Bath Cottage- Across from Siesta Key Beach Access-Cottage by Sea

Siesta Key cottage

2 bedrooms / 1 bathroom / sleeps 6

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$194

Rustic 2 Bedroom/ 2 Bath Cottage on the Bay at Sea Club 2 with Pool Access- 1A

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$217

Cute Siesta Key Cottage across from beach access!!-543

Siesta Key cottage

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$197

Incredible Cottage in Paradise ⭐Walk to the Beach or Village - Very Convenient

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 40 minutes

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$224

2 Bedroom/ 1 One Bath Gem Just Steps from Siesta Key Beach!!-Barefoot Bungalow

Siesta Key cottage

2 bedrooms / 1 bathroom / sleeps 4

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$171

Sea Club II Unit 2A - Amazing cottage on the bay!

Siesta Key cottage

3 bedrooms / 4 bathrooms / sleeps 10

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$283

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$228

NEW! Siesta Key ‘Casa Serena’ w/ Pvt Pool + Lanai!

Siesta Key cottage

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 35 minutes

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$201

Cute 2Bedroom/ 1Bath Cozy Cottage Steps from Siesta Key Beach!-Barefoot Bungalow

Siesta Key cottage

2 bedrooms / 1 bathroom / sleeps 6

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$171

Two Bedroom Two Bath Treehouse Cottage Located Near Siesta Beach!!Sea Club II 9A

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$171

NEW! Siesta Key Cottage - 4 Blocks to Main St!

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 3

Responds fast! avg. 1 hour 35 minutes

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$63

Siesta Key Beach Place - Starfish Cottage, Steps to the Sand, View of Pool

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$161

Darling Two Bedroom Two Bath Cottage Located Near Siesta Beach!!-Sea ClubII 8A

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$171

Cottage 15 SS

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$186

Great rentals within 20 miles that match your search

Anna Maria Island & Long Boat Key beaches a short walk away.

Cortez cottage

2 bedrooms / 1 bathroom / sleeps 4

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$135

SUNRISE HOLIDAY RETREAT

Sarasota cottage

/ 1 bathroom / sleeps 2

“Couldn't have asked for more!” Everything was perfect from the time we arrived until we left! The cottage was cute as can be and had absolutely everything one could want. I love that we had beach chairs, shelling net, buckets, cooler and towels to take with us to the beach.....what more do you need!? We enjoyed a lovely stroll to the beach the first day we were there. We could have walked everyday, but decided to drive and explore other close-by beaches. Can we talk about sunsets.....Wow! They are amazing here! The sand is amazing. The water is crystal blue/aqua.....amazing! Cynthia and her husband we at our disposal pretty much 24/7. Two of the nicest people you will ever met. I can honestly call them friends! As for the cottage.....B E A U T I F U L! Completely updated throughout. Everything you need to prepare a meal with and a wonderful patio to eat it on. We spent every night in the hot tub and between that and the big comfy bed; we slept amazing and woke up refreshed and ready for another day in Paradise! Thank you, Cynthia & Bruce You Will see us again!

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$111

2Bedroom Beach Cottage - 3 Miles to Siesta Key

Gulf Gate Estates cottage

2 bedrooms / 1 bathroom / sleeps 4

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$63

On the Beach Paradise d

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

“Absolutely beautiful!” Everything was perfect. Enjoyed coffee on the beach every morning and beautiful sunsets every evening. Can't wait to go back next year!

Responds fast! avg. 2 hours 19 minutes

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$206

HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!

Bradenton Beach cottage

4 bedrooms / 4 bathrooms / sleeps 15

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$148

Just 100 Steps Away from the White Sand of the World Renowned Siesta Beach

Sarasota cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$304

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

3 bedrooms / 2 bathrooms / sleeps 8

“Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of it. We will definitely be looking to rent from Tim again in the future.

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$119

" Fish Tales"- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$189

One Bedroom Cottage in Horseshoe Cove Resort, East Bradenton

Bradenton cottage

1 bedroom / 1 bathroom / sleeps 2

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$86

Charming Cottage #54548

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

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$173

PLAYA ESMERALDA/INNATTHEBEACH SUITES #2 BY BRIDE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 1 minutes

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$129

Cottage on walking Distance To Casey Key Beach

Nokomis cottage

1 bedroom / 1 bathroom / sleeps 2

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$92

PLAYA ESMERALDA/INNATTHEBEACH SUITES #4 BY BRIDGE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 1 minutes

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$124

Sarasota Pinecraft Cottage 2

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

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$172

One Bedroom Cottage on Vista Del Lago MH & RV Resort, 55+ Community

Oneco cottage

1 bedroom / 1 bathroom / sleeps 2

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$67

Sarasota Pinecraft Cottage

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

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$172

PLAYA ESMERALDA / INNATTHEBEACH SUITES # 1

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$114

Luxury Beach Cotttage

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

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Price per night from

$425

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$110

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$189

Las Brisas, Cottage on bay side of Island.

Bradenton Beach cottage

2 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$196

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cottages in Siesta Key

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