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Welcome to your perfect beach getaway on Longboat Key! This charming first-floor unit offers breathtaking views of the Gulf the moment you arrive. Just over 100 steps from your door, you'll find yourself on the soft white sands of Whitney Beach, one of the most pristine and peaceful stretches of...
Featured review
Wonderful. Great location. Great facilities. Well equipped. Wonderful for families. Beach is gorgeous.
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Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. The sunsets are breathtaking. You will love the beach views and fast Wi-Fi. This is a luxury rental. Condo has a single unit washer/dryer in one. There is a Islands West is the ideal...
Distance to beach: 0.0 miles to Longboat Key Beach - Condo is on the beach!
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The Beachcomber building and heated pool are located directly on the white sandy beach of Longboat Key! Suite 501 has an island view of Longboat Key with a partial view of Sarasota Bay from the 5th floor. Unit 501 is located ten steps to the elevator and 10 steps to the heated pool located directly on...
Featured review
Great location and staff,very clean and comfortable.Being on beach store was across street.Very quite at night so glad we didn't stay at Anna Marie Island to busy.Staff very professional, getting back to...
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Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot. Coveted lifestyle and location on a deep water canal in the heart of Longboat Key. This waterfront home has 125ft of seawall docking for a boat up to 30 ft. boat plus a jet ski lift and room for other water toys....
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Beautiful beachview unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors.The online system...
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Recently updated 2-bedroom, 2-bath canal-front villa on Longboat Key. This home offers modern finishes, water views, and easy access to the beach just a short walk away. Located in a quiet residential area in a small 2-unit coastal home (duplex).Features:Updated kitchen with new appliances Hurricane-impact...
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7th floor corner unit with balcony offering wide, sweeping view of the beach and Gulf. Both bedrooms offer clear view of Bay and downtown Sarasota. The unit has been newly updated and professionally decorated complete with tile floors, quartz countertops, high end furnishings and remote blinds. Living...
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Escape to a sparkly clean and relaxing beach getaway in this beautifully updated 2-bedroom, 1-bath condo, perfectly located in the heart of Longboat Key. Just a short stroll to the beach, local restaurants, grocery stores, and more, this unit is ideal for couples or families seeking comfort and convenience.The...
Featured review
This is not so much a review as it is an update for people concerned about the aftermath of Hurricane Milton. The city of Longboat Key has done an impressive job at cleaning up the hurricane’s mess....
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Live life on the beach---Private parking included!Beachplace is one of Longboat Key's premier vacation rental locations on the island!With amazing direct Gulf-front views, this sophisticated and chic 4th floor condo with balcony has it all!This condo has modern updates throughout including...
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Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Steps away from the longest stretch of private beach on Longboat Key and located on 30 acres of manicured grounds, Beachplace is one of the island’s most beautiful...
Distance to beach: 150 yards to Gulf Of Mexico
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Ground Floor Villa Condo- 1 Bedroom- Sleeps 2 - walk across the street to the beachBeautiful end unit attached villa in the charming walkable community of St. Judes on Longboat Key. Just a short walk to the private beach access and to the 32 acre Joan Durante Park FULL of fabulous tropical walking...
Featured review
This adorable rental was the perfect size for 2. It was very clean. I was so impressed how close we were to the beach
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For those who do not know Beachplace, it is more of a resort than it is a gated condo community. During the winter there are plenty of planned activities including a movie night once a week, a book club, pot luck dinners, tennis, pickle ball and more. This beautiful 5th floor corner unit has amazing...
Featured review
Arrived on the 1st of May what amazing place the Beachplace is right on the Gulf of Mexico the beach and the water was amazing. So many restaurants to visit and a Publix just down the road . Can’t recommend...
Distance to beach: 500 yards to Gulf of Mexico
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Little Palm on the bay in Longboat Key, Florida, a place to go when you want to relax and enjoy! Sunbathing, fishing, and boating right at your backdoor with the beach and pool only a short walk away! BOATERS, you can bring your boat or rent a boat to be available right out your back door. Don’t...
Featured review
I loved my month here. I would never have 5 people though. It is 600 sq. ft and 1 bath. There were two of us and it was fine. Lovely back area on a canal. Very quiet and nice people around. There...
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2 Bedrooms, 2 bathroom, gulf front, private beach, white sand, elevators. The condo is located directly on the beach waters of the Gulf of Mexico. The unit features a fully equipped kitchen, a dining room, a living room with sleeper sofa and 3 chairs, primary bedroom with king size bed with office...
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PENTHOUSE, DOUBLE BALCONIES, breathtaking wide sweeping straight on views of the Gulf and Bay make our Beachplace condo a true paradise on Longboat Key. This sought after resort is gated on the south end of the island close to the famous Saint Armands Circle, Publix’s and many highly rated restaurants....
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Newly renovated & furnished 1/1 second floor condo with wonderful view of Bishops Bayou on the uncrowded north end of Longboat Key. Whitney Beach has a beautiful natural stretch of beach as well as many amenities including tennis / pickleball courts, swimming pools, shuffleboard & boat docks...
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Spectacular Gulf Views and Breathtaking Sunsets – Renovated Beachfront Condo Relax and unwind at our newly renovated 1-bedroom, 1-bath condo on the pristine beaches of Longboat Key. With sweeping 180° Gulf views, modern upgrades, and easy beach access, this is one of the best values on the...
Featured review
This is an absolute must stay!! You have your own private beach, and everything is so close. The view from the balcony is breathtaking., by far the best place to have your coffee in the morning! The host...
Distance to beach: 50 yards to Our own private beach!
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Relax in this privately owned, Old Florida Charm, “coastal themed” ground floor condo located on the Southern Gulf side of Florida. The condo offers views of the Sarasota Bay, a community heated pool, hot tub, boat dock, and a three minute walk to the private beach with turquoise waters on...
Featured review
The condo was very very clean the amenities were excellent. You can walk to so many great eating places. The people we meet were all so friendly. Will be coming back.
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Views from every window 2 Bedroom/2 Bathroom (no one living above) corner end unit with access to a rooftop deck directly above this sunny and bright unobstructed panoramic view of Sarasota Bay with deeded beach access to one of the most pristine stretches of pearly white Gulf of Mexico sand directly...
Featured review
Lovely place with a great view of the bay. Well set up with all of the things you need. Owner very accomodating
Distance to beach: 500 yards to Whitney Beach
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Looking to step back in time to enjoy the "Old Florida Lifestyle''? Located in the quaint historic village of Longbeach on the northernmost end, is a lovely cottage steps from Sarasota Bay and 2 1/2 blocks from Gulf of Mexico with its own relaxing courtyard surrounded by beautiful lush...
Featured review
The cottage is in a great location on Longboat Key. It is small but having the outside patio was nice extra space to use. Quick walk and view of the bay, and not a long walk to the beach.
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Cedars East (0.6 mile walk) offers monthly memberships for tennis/pool/fitness center. The living area, kitchen and half bathroom are downstaris. Upstairs is the master bedroom with king bed and guest bedroom with 2 twins. The crib in the pictures has been removed and replaced with a desk & chair....
Featured review
We just spent 2 months at Tim’s condo and can’t speak highly enough about it! The location is perfect, mid island, walk to beach, on the canal which is just beautiful!! It’s great to have 2 floors...
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***CANAL VIEW HOME/WALK TO THE BEACH/NEWLY FURNISHED***Dreamed of living on an island? Look no further! Nice and quiet residential street in beautiful Longboat Key. This 2 bedroom, 1.5 bathroom sits on a water canal. Newly remodeled and furnished with a farmhouse coastal decor offering two bedrooms...
Featured review
We spent the holidays and January in this wonderful and well-appointed condo on LBK. Our daughter from St. Pete joined us for Christmas and a few other weekends. We couldn’t have been more comfortable....
Distance to beach: 5 feet to Just outside your door & window
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Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful! Located in very well-maintained and updated Longboat Harbor Towers.The barrier isle Longboat Key is a quiet, non-touristy location voted one of North America's top islands by Conde Nast...
Featured review
We enjoyed our stay & owners were very helpful for helping us when needed! Beautiful view of the Gulf! Unit was sparkling clean & well equipped & comfortable. We are returning next year as well. The property...
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Welcome to Longboat Key - you've stumbled on a unique hidden gem tucked away on the upper Gulf Coast of Florida. Small, private, and quiet - the key vacation that really makes you get away from it all. Our condominium in Bayport Beach and Tennis Club is a beautiful private retreat with unobstructed...
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This beautiful ground floor modern quiet condo offers direct views of Sarasota Bay and just steps from the stunning gulf beach. Inside you will find a modern, renovated interior. The living space boasts abundant natural light. The kitchen is bright with up to date appliances, and a breakfast bar that's...
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Enjoy seeing sunrise from the lanai or on the dock, and also enjoy sunset on the beach, directly across the street. The unit is completely renovated, nicely furnished, and well stocked - designed for those who love to cook. This 2 bedroom, 2 bath first floor unit with fantastic bayou views its located...
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Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning OCTOBER 1, 2025.Bayport Beach and Tennis Club is a beach to bay tropical oasis situated on 27 lushly landscaped acres on Longboat Key, FL. The grounds are meticulously maintained and provide a tranquil...
Featured review
The property owners are terrific. The apartment was impeccable and met all needs and beyond. Would definitely return
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Situated on Longboat Key, this secured and gated 1st floor NEWLY RENOVATED condo boasts water views throughout, 2 spacious lanai, each with own walk-down steps to water and pool, across the street to private beach with cabanas, grills, restrooms, etc. Great room, fully equipped kitchen (including microwave,...
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This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is...
Featured review
What a beautiful development Long Boat Harbour is! My wife and I stayed in unit E104 for 2 months. Haley is a very gracious host to allow us to stay in her home. We had such a wonderful time, we did...
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Looking to step back in time to enjoy the "Old Florida Lifestyle?" Located in the quaint historic village of Longbeach is this cozy one-family house with two queen bedrooms and a third private space that sleeps two more. Two fulls baths accommodates all. Kitchen includes microwave, coffee...
Distance to beach: 450 miles to Whitney Beach
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Escape. Brand newly remodeled, featuring a fully equipped kitchen, blending modern comforts of an air fryer/convection combo with cozy charm. The loft-style layout includes comfortable beds, ensuring restful nights in a peaceful setting.The cottage is bathed in natural light, thanks to large, well-placed...
Featured review
I traveled cross country from Oregon and had no idea anything about Florida! I booked this place randomly without ever having been to this area or the East coast. Thank god it turned out the way it did!...
Distance to beach: 0.1 miles to Private beach
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This WATERFRONT condo is very spacious, beautifully updated. Perfectly located within a minute of a private sandy beach and right along the waters edge of a salt water canal and intra coastal waterway. Enjoy the great water views that span the full width of the ground floor condo. Fishing, kayaking,...
Featured review
First, we have vacationed on Longboat for the past 5 years. Longboat is a special place where you feel relaxed, enjoy the gorgeous beach and the laid back feel compared to more touristy places in Florida....
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This sublime oceanfront studio (We own two more in the same building, plus one down the road - email for more info!) is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean,...
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This fabulous, 2000-square-foot, fourth story, corner, direct beachfront, condominium features spectacular views of the gulf and bay. Hear the waves from the master suite and enjoy a dinner on the screened lanai while viewing one of Longboat's incredible sunsets. Sip a morning coffee on the back...
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Great beach house on Longboat Key. Over 55 community two person occupancy limit with allowances for guests, no pets, parking for one vehicle.Next availability. July, August, September 2025, January 2026Tropical paradise awaits you on Longboat Key. The folks at Twin Shores call this The Green...
Featured review
I rented this adorable beach tiny house for 2 years during the season. Dec 2022-Apr 2023 & Nov 2023-Apr 2024. I cannot say enough about the house, location, community and the landlord. 2 Bed, 2 BA (1...
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Charming one-bedroom guest house featuring floor-to-ceiling windows, high vaulted ceilings, & an open kitchen. Balcony enclosed with heavy curtains, perfect for peaceful mornings & nights. Kick back, relax, in this calm, stylish space, capturing the essence of Old Florida. Experience peaceful...
Featured review
This place is amazing. The location could not be more perfect. The beach and three amazing restaurants are all within five minutes walking distance. The grounds are impeccably kept and the owner is very...
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Discover this newly rebuilt hurricane-resistant home at 701 Broadway St, Longboat Key, FL 34228 . Perfect for couples or small families seeking a serene vibe.Property Features2 bedrooms, 2 bathrooms. 1 bedroom guest house above garage, just one flight up. Fully gated backyard with swimming...
Featured review
Absolutely loved our stay at this Longboat Key cottage! It’s perfect if you work from home — fast, reliable Wi-Fi and a dreamy window seat made it easy (and enjoyable) to stay productive. The location...
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