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Oldsmar Cottages

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    ₹ 11,576 Average
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    21 Matching Rentals in the Oldsmar AreaView all 705 rentals
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    The following rentals are within 15 kilometres of Oldsmar.
    Cottage On The Water With Boat Dock1 / 18
    (2)Excellent
    Tarpon Springs
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach1 / 17
    (56)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    One bedroom Renovated Beach Cottage, Beach Bungalow, Luxury Beach Cabin,B&B1 / 36
    (1)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.1 / 49
    (8)Excellent
    Clearwater
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    Wow! What can i say?!!!Reminds me of my chuldhood in Florida. Lush tropicals and white powder sands within a short barefoot walk. Chairs & bicycles provided for guest at...
    Reviewed 26 April 2015
    We had my daughter's first birthday here. We planned on being out on the deck for the party but the hideaway was the perfect size for everyone. The staff was great and it really...
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    About this property
    Hideaway Large Beach Apartment sleep up to 10 Guests (7 is standard occupancy) with Two Queen Beds,one Full Bed, children's bunk beds , and full size sleeper sofa. Great value for large family or two families with children and pet .. This is not an upscale fancy Condo, but for way less than...
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    Clearwater, Florida 33767
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    Corner Cottage, 120 steps to the beach, Historic Beach House, sleeps  5, Pets ok1 / 34
    (35)Very good
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2018
    We stayed as a family in the hideaway cottage, pictures are same as in person. 7 adults 3 children had plenty of room. Nice beach decor, with nice counter tops and new...
    Reviewed 31 January 2018
    The picture above is indeed the cottage. Updated inside with hard surface counters, all necessary appliances and cooking needs. All tile floors. Fit our needs to the...
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    About this property
    Beach lovers have enjoyed Clearwater Cottages since the 1920;s. The Blue Corner Cottage is 150 steps from the beach with no streets to cross. 2017remodel with granite countertops, Stainless steel appliances, cute and cozy. Feature high vaulted ceilings with hand made wood beams, and original...
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    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Cottage Clearwater Bch, Heated Pool, 2/2 Tangerine Dream1 / 16
    (43)Excellent
    Clearwater
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    My family has stayed at this property numerous times and plan to return as often as possible. It is very well maintained and everything is as described. One of the best...
    Reviewed 10 May 2018
    Teresa and Max are great people to rent from. Their houses are kept well cleaned and maintained. We love the pools and the short walk to the beach. Once you are poolside it is...
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    About this property
    Our 2/2 Tangerine Dream vacation rental is part of a family friendly cottage resort located on the quiet Cyprus Avenue behind the Chapel by the Sea Church on the Island of Clearwater Beach. These beautiful homes are landscaped together in a tropical garden, with 2 heated pools, patio, and all...
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    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Charming Cottage in Clearwater1 / 46
    (7)Very good
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Shared Garden
    • Outdoor Dining Area
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2015
    The cottage was exactly as pictured and the owner was very quick to respond to all of our needs in the booking process. Check in was simple and the cottage was clean. My only...
    Reviewed 21 September 2014
    Very cute little cottage. Close to the beach.Perfect for one or couple looking to be out of typical hotel scene. Lovely garden and surroundings.Would definitely rebook.
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    About this property
    Charming cottage in a quiet neighborhood near many attractions. 5 miles from Clearwater Beach and 1 miles to delightful downtown Dunedin! Full kitchen-Stove, fridge, sink, microwave. Generously stocked with cookware and servingware. The cottage has it's own private driveway with room for...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pink Dolphin Cottage 100 Steps to the Beach Sleeps 7, Pets Okay, Value1 / 32
    (5)Very good
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We are from Iowa and do not get down to Florida very often but my husband was recently deployed for a year and is now home. We wanted to take a family vacation which started in...
    Reviewed 3 November 2018
    Arrived to find our original booked cottage Pink Dolphin already in use so Capt Al upgraded us to the Captains House.This is not your usual corporate box accommodation. The...
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    About this property
    Restored Beach Cottage, daily rentals, Private wood deck Tropical Backyard Just remodeled 1925 beach cottage 100 steps from the beach. Pink Dolphin Cottage features Samsung Smart Stainless Steel appliances, granite countertops with white beaded pine cabinets. Families have enjoyed these cute...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Coconut Cabana 2/1 Cottage, sleeps 4, Two heated pools, Walk to Beach1 / 14
    (14)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Porch
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2018
    Tom and I wanted to thank you for another great stay in orange blossom it is always clean and i love the access to the 2 pools and the washer and dryer Thanks again for your...
    Reviewed 24 August 2018
    We loved our stay the pools was fun there place is clean and close to everything we walked everywhere lol and her and her husband are down to earth good people we will be going...
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    About this property
    The Coconut Cabana is a fully equipped and supplied, 2 bedroom, 1 bath vacation rental. This cottage has central A/C, WiFI, complimentary W/D and more. The cottage has a living room, flatscreen cable Smart TV, full kitchen, table, two bedrooms, each with queen bed, closets, ceiling fans, bathroom...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A perfect place for a couple, Mango Tango Cottage1 / 12
    (25)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Porch
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2018
    This is a fantastic place. Easy walking distance to the beach, restaurants, and shopping. The pools are great. Just the right size to float in or just sit and relax. There are...
    Reviewed 21 February 2018
    Mango Tango Cottage is small but perfect for one person or a couple. Owners Teresa and Max are very helpful and the property is well maintained. Cottage has a well stocked...
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    About this property
    What a great place for a couple. Our tropical Mango Tango, one bedroom, one bathroom vacation rental is part of a cottage resort complex located on the quiet Cyprus Avenue behind the Chapel By The Sea Church. These beautiful homes are landscaped together in a tropical garden, with palm trees and...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Restored Beach Cottage , Beach Block, Pets Okay, Sleeps 6, Tiki Hut1 / 26
    (1)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Value for familiy, 2 adults , up to 4 kids and pets, Beach side , 1925 Real Beach Cottage just 200 steps to the sand, Clearwater Beach, 5 blocks walk to Pier 60, in quiet historic part of Clearwater Beach called Clearwater Cottages, where there are several beach houses. 2016 remodel White...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Seaside Beach Cottage 16 Steps to the Beach1 / 29
    (2)Very good
    Clearwater
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2017
    Its an older house that has been very nicely renovated. Husband and myself stayed in poolhouse and kids and grandkids in main house. We loved the pool. Washer and dryer was...
    Reviewed 15 August 2017
    Overall we had a lovely time at this unit and it is within walking distance of the main hub of clearwater which is great. The beach is also just out the front door and the pool...
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    About this property
    Military Discount!! As a thank you for serving our country and protecting our freedom we would like to offer a Military Discount of 5% fr all Active Duty, Retired Military and Veterans of All Foreign Wars from September 2nd 2017 through December 18th 2018 \'excluding holidays\'. Please inform the...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
    • Parking
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 New Attic Loft Remodel. . Very beachy feel with all white beaded pine walls and distressed wood floors. Everything is brand new with quality bedding and fun, funky decor; Teaser view of the Gulf of Mexico from window. Great for family with lots of kids. No kitchen, but does have oudoor...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Pelican Cottage: A Tropical Paradise1 / 21
    (5)Excellent
    Tarpon Springs
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    Pelican Cottage, Tarpon Springs, FL. We completely enjoyed our two week stay and felt very much at home. Everything was neat,clean and tastefully decorated. It was set up so...
    Reviewed 17 February 2017
    Nice and close to the sponge docks. Clean and comfortable-everything we could need. Our dog had her own private fenced yard. Would stay there again.
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    About this property
    Tucked neatly into the NE corner of our property, sun-drenched Pelican Cottage offers everything you'll need for a private, relaxing, quiet getaway within walking distance to the Sponge Docks, Spring Bayou, the Pinellas Trail & more in beautiful Tarpon Springs, Florida. The Space The 528 sq. ft....
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    Location Information
    Tarpon Springs, Florida 34689
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico1 / 20
    (42)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2018
    This is our 3rd visit to the cottages! We’ve stayed in 3 different cottages and loved each one! Location is wonderful, very close to beach and restaurants. All cottages are...
    Reviewed 5 May 2018
    Second year we’ve been there and we love it. Walking distance to everything in Clearwater Beach. Quieter part of the island. Teresa and Max are great and very responsive. Kid...
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    About this property
    Our 2/1 Banana Breeze/Lazy Lemon vacation home is part of a family friendly self-catering 7 cottage resort located on the quiet Cyprus Avenue behind the Chapel by the Sea Church, on Clearwater Beach Island. These beautiful homes are landscaped together in a tropical garden, with 2 new heated pools,...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Taylor's Tavern: 2 Blocks off Main Street!1 / 13
    (8)Excellent
    Safety Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2018
    Great spot, private and very clean. This adorable efficiency had just what we needed for our stay. You are a 2 minute walk from the cutest variety of shops & restaurants...
    Reviewed 1 February 2018
    Very quaint, cute, clean and perfect location. Convenience to lots of awesome restaurants and shopping.
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    About this property
    In the HEART of Safety Harbor, Florida, “Taylor's Tavern” is a charming 1 bedroom / 1 bath cottage, located on the grounds of a 1926 historical bungalow in the redevelopment district of downtown. It is decorated with romantic elegance and just 2 blocks from Main Street! It's a perfect get-a-way to...
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    Location Information
    Safety Harbor, Florida 34695
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy Cottage Clearwater1 / 30
    (3)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    We weren't sure what to expect when we booked our stay. We found it to be relaxing and comfortable. The shared backyard is nice for pets and we even learned about the...
    Reviewed 10 April 2017
    Sharon and John were wonderful hosts. The cottage was immaculate and well equipped. The bed was very comfortable. We especially enjoyed our morning coffee on the front, private...
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    About this property
    Centrally Located in a Beautiful Part of Clearwater, Florida minutes from the coast and award winning beaches. The Cottage offers a Fully Equipped kitchen with Full size appliances. Also included is High speed wireless internet and Brand New Flat Screened TV's. There is a separate bedroom with a...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Exclusive Quiet Beach Cottage - Monthly rental1 / 20
    (1)Excellent
    Clearwater
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like exclusive quiet beaches, this is it! This cute, 2 bedroom house is 2 blocks from a private beach in an exclusive area on north Clearwater Beach. There is a private entrance to the beach with a shower. The house has a private, fenced backyard and is located across the street from the...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Shades of Gray Cottage - Private Luxury in Dunedin1 / 19
    (1)Excellent
    Dunedin
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    Cozy relaxing cottage, tastefully decorated with everything you need. A quick drive or bike ride to downtown Dunedin or to the beaches, We are looking forward to another visit...
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    About this property
    Come enjoy our beautiful cottage in delightful Dunedin! You'll enjoy your own cozy and private little home with a full kitchen, private deck and artistic decor. You will be close to downtown Dunedin, the gulf of Mexico, fabulous restaurants and the world famous Honeymoon Island State Park and...
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    Dunedin, Florida 34698
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turned off by noisy concrete condos with stairs and bad parking? If so, this single-story cottage complete with a large outdoor space is ideal for you! Nestled in a quaint and quiet, residential neighborhood, Bertie's Nest is completely new inside and is the perfect place for turn-key, comfortable...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Clearwater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay ** All the sun and surf of Clearwater Beach awaits at this charming 3-bedroom, 2-bath vacation rental cottage - perfect for a family of 6. Just across the street...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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