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Looking for a luxurious coastal escape with a serene atmosphere? Our monthly rentals in Longboat Key, Florida, offer the perfect retreat for those seeking pristine beaches, stunning Gulf views, and a peaceful getaway. Whether you’re planning a winter retreat or a long-term vacation, Longboat Key provides an idyllic setting for relaxation and adventure.
Key Amenities
About this property
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: 0.1 miles to Private beach
Key Amenities
About this property
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....
Key Amenities
About this property
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...
Key Amenities
About this property
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...
Distance to beach: 0.3 miles to Gulf Of Mexico
Key Amenities
About this property
Bring your boat or just enjoy the view of the canal in this coastal townhome! It’s on the North end of LBK on a deep water canal with quick access to Sarasota Bay and the Gulf of Mexico. The location is ideal near Harry’s Restaurant and Store and just steps from the Deeded Beach Front, Durante...
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Key Amenities
About this property
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...
Key Amenities
About this property
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,...
Distance to beach: 500 yards to Whitney Beach
Key Amenities
About this property
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.
Key Amenities
About this property
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...
Distance to beach: 0.5 miles to Longboat
Key Amenities
About this property
Imagine waking up to dolphins playing just beyond your window. This exquisitely renovated Longboat Key luxury waterfront home offers breathtaking "Big Bayfront" views and unparalleled access to the Gulf of Mexico. Boater's Dream: • Direct access to the Gulf for fishing or cruising • Private...
Distance to beach: 450 miles to Whitney Beach
Key Amenities
About this property
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!...
Key Amenities
About this property
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...
Key Amenities
About this property
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...
Key Amenities
About this property
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...
Key Amenities
About this property
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
Key Amenities
About this property
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...
Explore a variety of monthly rentals in Longboat Key, including beachfront condos, canal-front homes, and pet-friendly options. Whether you’re seeking a private retreat or proximity to the beach, you’ll find the perfect rental to meet your needs. Enjoy the convenience of a long-term stay in this tranquil Southwest Florida destination.
Secure your ideal long-term rental in Longboat Key now. Browse our listings to find the perfect property for your extended stay. Whether you’re escaping winter or planning a summer retreat, Longboat Key offers endless opportunities to relax and unwind.
It’s never too early to book your next Longboat Key getaway. Reserve your preferred rental now to ensure availability during your desired dates.
Group-Friendly Rentals: Spacious homes with private pools and large living spaces make Longboat Key perfect for group vacations or family reunions.
Romantic Escapes for Couples: Enjoy beachfront views, quiet bays, and cozy condos ideal for romantic getaways.
Winter Retreats for Snowbirds: Longboat Key’s mild winter weather and welcoming community make it a favorite for snowbirds seeking a warm escape.
Reserve your winter retreat in Longboat Key today. Experience the sunshine, warm weather, and laid-back lifestyle that make Longboat Key a top choice for snowbirds and long-term visitors.
💰 Highest rates
January and February
🎉 Busiest month
March
🏠 Popular home types
Beachfront condos and private homes
🔥 Hottest months
July and August
❄️ Coldest months
January and February
☔ Rainiest months
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
January through March
🍂 Quietest months
September and October
🌊 Best beach months
April through June
🏌️ Best golfing months
November through April
🎨 Top cultural events
Longboat Key Art Festival (February), St. Armands Circle Craft Festival (January)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
January through March
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