Clearwater, FL Vacation Rentals

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88 cottages

Charming Cottage in Clearwater

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 3

“Accommodations were very agreeable.” We were in Florida as a pre-anniversary trip and a nostalgia one having visited the Clearwater area for 13 years with our last trip being in 2013. Our main form of entertainment was to attend three spring training baseball games.

Responds fast! avg. 3 hours 1 minutes

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$79

Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.

Clearwater cottage

3 bedrooms / 1 bathroom / sleeps 10

“Best weekend to the end of the summer” The hideawy cottage was perfect for what we needed peacefully, quite and dog friendly that what was the best part! The staff was great and professional and helpful. This was a perfect getaway for my birhtday celebration. I am turly coming back to take another mini vacation it was all the comfronts of home. I would like to thank the staff at Blue Wave Condo Suites for a wonderfully experience and this will be my new vacation spot when I travel back to Clearwater Beach.

Responds fast! avg. 1 hour 39 minutes

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$411

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 39 minutes

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$182

Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 5

“A wonderful and Perfect Oasis in Clearwater Beach” Thanks so much to Teresa & Max for a fantastic week in Key Lime Sweet Cottage (which is a sister villa of Orange Blossom Cottage). We could not fault the Villa and landscaped gardens, pools in any way. The beautiful accommodation had more than we expected and the attention to detail was second to none. The Villa's have everything any family could need made all the difference. Many places have the bare minimum but the villa's had more than plenty of everything. Having the 42" TV & sports channels made all the difference to our lads especially during the basketball playoff's. Teresa and Max were excellent hosts looking after our very late arrival really make the difference which was very much appreciated.The grounds are beautifully landscaped and really well kept and with the 2 swimming pools just make it the perfect oasis for any family. And with the recreation Center just across the road was great as we could use the Gym, play basketball and tennis and large swimming pool was great. We just loved Clearwater Beach and we thought is was so beautiful, clean and well kept. The beach, the sunsets, the restaurants, shops and gave us all a wonderful experience and many happy memories to take back with us. Also all Teresa & Max's comprehensive emails and information before our trip was excellent and we just knew it was going to be somewhere special. They were great hosts during our stay with much good advise and information throughout. The location was just perfect in a quiet street at the end of the the town but yet very just 2 minutes from the beach and restaurants. We have no hesitation in giving 10 out of 10 and would and will highly recommend your Villa's to all. We have been on many family holidays together but this week ranks up at the very top. Again many thanks again to both Teresa & Max for a wonderful week in their wonderful oasis on Cyrus ave, Clearwater Beach, Florida. Gerry, Mary, Ronan, Conor & Sean White. Dublin Ireland

Responds fast! avg. 50 minutes

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$122

Cozy Cottage Clearwater

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 3

“Extremely Friendly and Accommodating Hosts!” Sharon was extremely helpful in accommodating us on very short notice. Her personal care and attention made us feel right at home, and we would definitely plan on staying at the cozy cottage in the future! The cottage is just across the bridge from the beach in Clearwater, with its amazing white sand and the warm Gulf of Mexico. Honeymoon Beach, Caldesi Island, Dunedin, and Indian Rocks Beach are all within a short (15-30 min) drive, making this a prime location for staying in the Clearwater area.

Responds fast! avg. 3 hours 11 minutes

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$134

Cottage Clearwater Bch, Heated Pool, 2/2 Tangerine Dream

Clearwater cottage

2 bedrooms / 2 bathrooms / sleeps 5

“Another great week!” My husband works for a travel company. We have access to many properties in Florida at greatly reduced rates but we continue to come to our favorite spot in Clearwater. This was our fourth year at Cyprus avenue Beach Rentals and we left knowing we would return again. Every little detail is covered. When we arrive we know that we will have everything we need and we will feel as if we are in our own little private resort. We love having the small pool right at our back door and the ability to walk to the beach in minutes. In the evenings we like to walk to Pier 60 for entertainment, dinner or ice cream. Afterwards we know we can return to our little private oasis. In the morning it is so relaxing sitting out back and enjoying the surroundings. Our kids love to swim first thing in the morning. The rooms are lovely, the beds are comfortable and the towels are soft. The owners, Max and Teresa, are meticulous and the property is well kept. We often laugh that a weed would not dare grow on their property. Clearwater is a great place for all ages and we will return soon.

Responds fast! avg. 50 minutes

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$145

Corner Cottage, 120 steps to the beach, Historic Beach House, sleeps 5, Pets ok

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 5

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

Responds fast! avg. 1 hour 39 minutes

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$205

Pink Dolphin Cottage 100 Steps to the Beach Sleeps 7, Pets Okay, Value

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 39 minutes

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$286

Hidden Treasure Private Cottage Gem in North Clearwater Beach

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 6

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$97

New Listing! Hidden paradise 2 blks from water, ez parking, great location.

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 4

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$61

Fun Baywatch Loft , Pets OK, new renovated beach loft, beach block

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 39 minutes

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$160

A perfect place for a couple, Mango Tango Cottage

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 2

“Very clean and nice.” Very nice location. We walked everywhere. Had a nice relaxing vacation. Two pools in the complex, and you could use either pool. Beach was also within walking distance.

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$98

Restored Beach Cottage , Beach Block, Pets Okay, Sleeps 6, Tiki Hut

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 6

“Great pet friendly place!!” The place was awesome!! Very short walk to the beach and a very cozy place. We brought our two dogs with us and they loved the place. The location was great. There is a park close by where we could walk our dogs. We were also close enough to the center of the beach so that we could walk to the shops.

Responds fast! avg. 1 hour 39 minutes

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$240

Seaside Beach Cottage Steps to the Beach

Clearwater cottage

4 bedrooms / 3 bathrooms / sleeps 11

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$242

Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 33 minutes

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$126

Coconut Cabana 2/1 Cottage, sleeps 4, Two heated pools, Walk to Beach

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 31 minutes

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$109

Exclusive Quiet Beach Cottage - Monthly rental

Clearwater cottage

2 bedrooms / 3 bathrooms / sleeps 6

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$229

Great rentals within 20 miles that match your search

One Bedroom Cottage in Rainbow Village RV Resort in Vibrant Largo

Largo cottage

1 bedroom / 1 bathroom / sleeps 4

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$75

Gulffront Cottages Sandy Shores/PATIO

Indian Rocks Beach cottage

1 bedroom / 1 bathroom / sleeps 4

“Family vacation” Wonderful place gorgeous views comfortable and relaxing you couldn't ask for more in a vacation spot great location.

Responds fast! avg. 1 hour 28 minutes

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$144

Quaint and charming studio cottage by the beach

Madeira Beach cottage

/ 1 bathroom / sleeps 4

“Great place” We enjoyed our vacation in this cozy cottage very much. It is well supplied, clean and comfortable. Love the high ceiling and the Murphy bed which gives a more spacious appeal to the small space. Appliances are good. The heated pool is deep and fabulous on warm days and the beach is just across the street and always gorgeous. There are many close restaurants and places to shop. The managers are nice and helpful. I highly recommend this place and would gladly stay here again.

Responds fast! avg. 34 minutes

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$86

Blue Heron Cottage

Indian Rocks Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

“Wouldn't stay anywhere else on Gulf Blvd.” My family has stayed at Blue Heron Cottages many times. What keeps us coming back is the fact they are sooo pet friendly. Our dogs are part of the family and are always welcome at Blue Heron. Cindy is just the best and after one stay she felt like an old friend. It is the perfect location on Gulf Blvd. close to Clearwater as well as St.Pete. Plus easy access to Tampa. Also the heated pool is the best ever. Can't wait for our next get away. Soon I hope !!!

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$149

Gulffront Cottages Sandy Shores/Garden

Indian Rocks Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 28 minutes

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$137

Gulf Views from this Beachfront Studio Apt

Indian Shores cottage

1 bedroom / 1 bathroom / sleeps 2

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$189

Cottage By The Water With Boat Dock

Tarpon Springs cottage

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 16 minutes

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$86

Serenity By The Sea Cottage

Indian Shores cottage

2 bedrooms / 1 bathroom / sleeps 5

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$205

Starfish Cottages One Bedroom

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$99

The Yellow Cottage with heated pool

Indian Rocks Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 31 minutes

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$229

Ready for a vacation?

Madeira Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

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$159

"Carson's Surf Shack" Quaint! Cool! So Cute! Old Florida Style Cottage!

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 30 minutes

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$98

Wyatt Beach House

Treasure Island cottage

2 bedrooms / 2 bathrooms / sleeps 5

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$213

W22- Cozy St Pete Beach House 2ndfl. w/Bikes&Wifi

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 4

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$161

The Flamingo Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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$172

Serenity By The Sea Suite B

Indian Shores cottage

1 bedroom / 1 bathroom / sleeps 4

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$125

REDINGTON BEACH COTTAGE 1

Redington Shores cottage

2 bedrooms / 2 bathrooms / sleeps 4

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$205

(N22)Island Beach House 2ndfloor w/ Wifi & Bikes

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 4

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$186

The Flip Flop Inn Two Bedroom with Heated Pool

Indian Rocks Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 31 minutes

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$189

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$138

Charming studio cottage at Gulf Gardens Resort in Madeira Beach

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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$92

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