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    Beach Resort Retreat

    5.0 (1 review)
    Open Open 24 hours

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    2 years ago

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    Island Paradise Cottages & Apts of Madeira Beach - Sparkling Pool!  Authentic Tiki Hut & More

    Island Paradise Cottages & Apts of Madeira Beach

    5.0(3 reviews)
    6.7 miMadeira-Redington

    Awesome stay! Highly recommended!…read more We needed a quiet, relaxing vacation where we could bring our dog. Island Paradise delivered. The couple who owns them is super nice and so helpful with our visit. The cottages are nice and you can tell some well-thought effort went into updating them. Everything there was quiet. The pool was nice and the tiki hut made for a nice place to chat with fellow relaxers. The beach is a short five minute walk. With a less-than ten minute walk, you're at John's Pass with shopping, restaurants and bars. We had planned on going to other places while visiting, but we barely left the radius around the cottages.

    We had chosen to go to Florida on vacation with our two kids (aged 8 months and 3,5 years) for some…read moreweeks vacation and were so lucky to find this place. The villas are perfect for staying for a longer time and everything you could wish for in a kitchen is there. It is extremely clean, very beautifully decorated and just perfect. The hosts (june and Bill) are so friendly and helpful that we felt like family when we left. The other people staying there were also extremely nice and the atmosphere was wonderful. This was supported by the tradition that everybody staying there would gather for a glass of wine or a drink at around 5 in the afternoon in the tiki-hut. Even though we were the only ones with children we felt so welcome. I would love to go there again and I am sure that we would feel just as welcome the next time. We stayed in Villa Paradiso, which was the largest of the villas, but I also saw the inside of some of the other villas and they looked just as nice. The beach was a short 3 min walk from the cottages and John's Pass was around 5-10 minutes away when walking.

    Legacy Vacation Resort Indian Shores - Laundry Facilities

    Legacy Vacation Resort Indian Shores

    4.4(14 reviews)
    1.5 miMadeira-Redington

    The Legacy vacation club (we aren't owners) can be rented for nights/weeks or traded into with RCI…read more We booked this 2 bedroom 2 years ago planning to have a party, but Covid 19 had different plans for us! Nevertheless, we had a great time here on our own with a spacious condo on the canal and intercoastal waterway in Indian Shores. We walked to the beach everyday to get a power walk for an hour. The temperature was cool in the mornings. We hung by the pool for a little while each day, usually walked to lunch at the many restaurants nearby. One day, we took the free trolley to lunch. This property is conveniently located on Gulf Blvd. The trolley stops are close, and you can head south towards St. Petersburg or north to Clearwater with stops along the way. The condos were completely remodeled recently and the pier out back was also partially rebuilt. You can fish or pull up a boat to the pier. There are grills out there and tables to have a picnic on the water. Grocery stores are not that close....we borrowed a car from my sister for our grocery visit. It was about 3 miles to a Publix in Largo that had everything! We didn't use the workout room or game room, but they have those. They have a few snacks and drinks in the main office. Check-in with Petra was easy. They even gave us our condo early. I even received a call from "G" prior to our trip to find out if we needed anything or had any concerns. It was nice to know that they were expecting us! The kitchen was modestly equipped, but no kitchen shears. They had a toaster, coffee maker and blender, some sharp knives, kitchen utensils, wine glasses, coffee mugs, plates, glasses and silverware. I think if you aren't planning to do major cooking, you will be fine. The freezer has an ice maker, but if you need ice right away, just buy a bag while the machine catches up! The soaps are all supplied. The showers have dispensers for shampoo, conditioner and body wash. There is no lotion, so bring that. The bedrooms both had small decks with two chairs. There was one small table to put in between the chairs. It was great to have coffee out there in the morning. They have laundry baskets in the rooms, but you have to go to the laundry room to do laundry. The soap is free, but the washer and dryer are not. The TV's are huge! We had 3 flat screens, one in main area and one in each bedroom. The furniture in the living room wasn't super comfortable, but was fine. The dining table had 6 chairs. All in all, very home-like and spacious. The people were very nice. The employees always asked how we were doing and if we needed anything. The early check-in was so nice. There is covered parking for all guests. Certified B corporation/recycling We would stay here again and hope to stay here again!!

    Absolutely beautiful resort. Very friendly staff, and very accommodating too! They are up to code…read morewith all the Covid regulations, and made my wife and my anniversary one to remember! Will definitely be staying here again! Best value for money in all of the Indian Shores/Indian rocks area. They even have indoor parking! The rooms were spotless, spacious, and very well designed, and we were within 1 min walk to the beach. Couldn't be happier with my stay, and I'm recommending to all my friends and family.

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    Legacy Vacation Resort Indian Shores - Pool

    Pool

    Legacy Vacation Resort Indian Shores
    Legacy Vacation Resort Indian Shores - Pool

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    Tommy's on the Beach - Tommy's on the Beach, an original beach front cottage

    Tommy's on the Beach

    5.0(2 reviews)
    2.2 mi

    We stayed last minute in the North Unit May 26-June 1, 2020. Patrice was so amazing and so…read moreaccommodating to our family from Ohio. We had been restrictively locked down and needed a fresh breath and mental break. This quaint cottage provided just that and more. The view and beach access was more than awesome. The fun and cute backyard was perfect for our family to enjoy a beachside fire, twinkle lights, shuffleboard, lawn games, kayak, paddleboards etc. It was fully stocked with everything you'd ever want for the beach - beach bag, umbrellas, chairs, toys, fishing poles, nets, floats etc. The free on site laundry and laundry supplies was such a generous offering. The cottage was clean, well kept, fully stocked with kitchen and bathroom essentials and then some extra. We brought our Shiba Inu and he loved being able to watch out the back glass to see us at the beach! The back deck and views are magnificent. Our beds were clean and comfy. The shower had perfect water pressure for thick haired families like ours. The French bakery in front had the most delicious pastries and quiche offerings. We absolutely loved Tommy's on the Beach and can't wait to return very soon.

    If you're planning a fun, relaxing getaway in the Tampa Bay, Florida area, 'Tommy's On The Beach'…read moreoceanfront rental is a 'MUST DO'! This 3 unit rental located in Indian Rocks Beach, is the perfect place for a couple/family to experience a little piece of 'Paradise' with all the comforts and feel of an 'old Florida home'. My husband and I stayed in the 'South Unit', which offers 2 large bedrooms, full bath+, and beautiful open concept kitchen, dining and living room area. The unit is whimsically decorated with a fun Florida decor and is fully equipped with every ammenity needed to have a great vacation...all you need to bring is 'you'! The expansive courtyard that boarders the abundantly shelled beach, offers 2 grills, 3 umbrella dressed table and chairs, and a welcoming hammock under the palms. The frosting on the cake is the amazing view; from the courtyard and from the spacious deck. Every morning you'll awaken to the sights and sounds of the beach on the Gulf ~ pelicans, gulls, 'friendly egrets', an occasional dolphin swimming by ~ and in the evening you can watch the sunset and experience the awesome colors the sky presents as the evening goes on. If the moonlight isn't enough for you once the darkenss settles in, you may want to throw a log on the outdoor fire pit to brighten up your night! And for the kids??? 'Tommy's' provides every necessity for a young family from sand chairs, beach umbrellas, boogie boards, floats, fishing poles, socker balls, footballs, horseshoes and shuffleboard; to a highchair, strollers, and even a pack n' play! So no matter what your family size, 2 or 6, there's something for everyone at 'Tommy's'! With permission, 'Tommy's' is a pet friendly rental...no need to leave Rover behind! The location is perfect; a short ride north through Clearwater Beach, Dunedin, Tarpon Springs as well as a short ride south through Madeira Beach to St. Pete. The area is chuck full of wonderful restaurants and there's no limit to activities for all ages. So if you're thinking about where to spend your next vacation, I guarantee you'll make wonderful memories at 'Tommy's On The Beach'!

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    Tommy's on the Beach
    Tommy's on the Beach
    Tommy's on the Beach

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    Holiday Villas II - Plumlee Vacation Rentals

    Holiday Villas II - Plumlee Vacation Rentals

    3.8(4 reviews)
    1.6 miMadeira-Redington

    Beautiful beach behind condo. Fridge leaked on floor and ruined food, toilet kept running, garage…read more(bottom of condo) is deteriorating pretty bad, huge roaches. Definitely room for repairs. (Reported) Customer service was incredible and it was great renting the umbrella and chairs for only $70 for a week.

    My mom and I rented a 5th floor condo in September 2015 for a week and enjoyed our stay until the…read morelast day. The condo was beautiful and had a breath taking view of the beach from the balcony. It was spacious with two bedrooms and two bathrooms. The property was quiet and guests and residents were pleasant. The owners resided out of town and rented it out via online. There are designated parking spots with one spot per condo, otherwise you have to retrieve a parking pass from the office for an additional vehicle to park on the premises. The elevators and pool gate are operated by entering a code number. Unfortunately, the last day became a nightmare. Check out time was at 11am and we were running a little behind in leaving. From my past experience, most rental facilities will cut you a little slack on the check out time. It was about 11:45am and I had about 2 more trips of packing up the car before we left. As I was putting things in the car, a couple drove past slowly and rolled down the window and said check out time was 11am. I apologized and explained that we were running a bit behind in checking out and that I only had a couple of more things to pack up. The woman got out of the car and kept harassing me about check out time being at 11am and just kept antagonizing me. I continued to profusely apologize and I told her there was nothing else I could do. I was going as fast as I could. She then went upstairs and barged in on my poor mom who had no idea what was going on while the man parked their car in another spot. I happened to get on the elevator at the same time with him and he continued to harass me on the elevator and said "what part of 11am check out time do you not understand" and he said "they have a "blacklist" for people like us." Apparently, this couple lived locally and worked as housekeepers for the owners. He said the owners had a death in the family and were on their way to the condo and they needed to get it ready before they arrived. I told him I was very sorry for their loss and at that point, I was so upset I started crying and I could tell he then felt bad. My mom and I gathered the remainder of our belongings and as we were leaving the woman said she was sorry for her husband making me cry. I told them I was sorry for their loss and for the inconvenience we caused, but we would not be back. Those owners lost our business thanks to their rude and completely unprofessional housekeepers.

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    Holiday Villas II - Plumlee Vacation Rentals
    Holiday Villas II - Plumlee Vacation Rentals - Holiday Villa II Gulf Front vacation rental on Indian Shores, Florida.  Amazing sunsets every night!

    Holiday Villa II Gulf Front vacation rental on Indian Shores, Florida. Amazing sunsets every night!

    Holiday Villas II - Plumlee Vacation Rentals - Holiday Villa II, Indian Shores, Florida

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    Holiday Villa II, Indian Shores, Florida

    Beach Resort Retreat - vacation_rentals - Updated May 2026

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