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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
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Jacuzzi or hot tub
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DVD player
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Cot available
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Dishwasher
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Private outdoor pool (heated)
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Cribs
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Boat available
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Bicycles available
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Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
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Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
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61 cottages

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Brand New Renovation Sea Waves Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$492

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$343

Tarpon Tree House

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 41 minutes

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Price per night from

$378

Coquina Cottage A

Anna Maria cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 41 minutes

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Price per night from

$180

Great rentals within 20 miles that match your search

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.

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$403

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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Price per night from

$165

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$219

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$259

The Sunshine Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 48 minutes

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Price per night from

$173

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

Bradenton Beach cottage

4 bedrooms / 4 bathrooms / sleeps 15

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Price per night from

$296

On the Beach Paradise u

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$208

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!

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Price per night from

$208

March 19-26, 2022 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$691

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$374

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$141

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$339

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$316

Guest Cottage, clean, convenient and remodeled.

Sarasota cottage

/ 1 bathroom / sleeps 2

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

Responds fast! avg. 3 hours 47 minutes

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Price per night from

$201

Beachhouse-Rental kingbed w/2 bikes, WIFI, steps 2 beach

St. Pete Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$346

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$164

The Anchor- A two bedroom cottage minutes walking to beach.

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

“Lovely cottage with great location” Our time at Sea Stories was memorable. We enjoyed the location for the beach and the restaurants. The cottage was adorable with everything we needed. Wendy was so helpful in solving a problem we had with sleeping arrangements for three girls. We will come back to Anna Maria Island with Sea Stories in mind. Thank you Wendy for all your help!

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Price per night from

$373

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$210

Island Living! Steps 2 Beach w/bikes+parking

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$213

Comfortable Two Bedroom Cottage Just Steps To The Beach

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

“We would like to come back” I stayed here last year with my wife and two kids. I'm on the page again because I'd like to come back. Can't remember his name anymore but the guy at itrip was really good to work with. The place was spotless. The neighbor were quiet and virtually out of sight. The beach is maybe 150 yards from the house. It was a good experience for my whole family. Only and I mean only negative is that the surrounding area is old and a little run down. That doesn't mean it's a bad or rough area, either. We live on the other side of Pinellas. This place was a great place for a restful vacation - no tiring travel involved, right on the beach, and cheap rates. Like I was saying at the start, we'd like to come back soon at some point.

Responds fast! avg. 3 minutes

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Price per night from

$109

As Close to the Gulf as Allowed! The View from the Porch is Amazing. All Updat

Treasure Island cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

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Price per night from

$153

Fully Equipped Cottage Directly on the Beach! Comfort and an Unbeatable Locatio

Treasure Island cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

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Price per night from

$148

Perfection with a Total Renovation. A Private, Spacious and Modern Home Away Fro

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

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Price per night from

$134

Leave Your Troubles Behind. Relaxation, Value, and Peace in the Heart of Madeira

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

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$124

3 Min Walk to the Beach - Value & Comfort! Freshly Renovated, Free Wifi, Nice Ma

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

“Madeira Beach Cottage” Beautiful home located in a great location. Very responsive and receptive property owner. Would recommend to anyone seeking to visit the area

Responds fast! avg. 3 minutes

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Price per night from

$109

Steps to Sand - Standalone Beachfront Cottage w/ Picnic Area, Picnic Table & BBQ

Treasure Island cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

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Price per night from

$134

Viewing 38 of 61
cottages in Anna Maria

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Cottages Anna Maria

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61 cottages

Viewing 38 of 61cottages in Anna Maria

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Viewing 38 of 61
cottages in Anna Maria