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.
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Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse condo located on the 15th floor of Islands West Complex. You will love the beach views and fast Wi-Fi. Master bedroom with King bed has amazing views of the Bay and the Sarasota Downtown ...
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AS OF 9/29/24 WE ARE OPEN . No damage to unit DIRECTLY on the GULF. WITH PRIVATE BEACH Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ...
Key Amenities
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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 ...
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 ...
Key Amenities
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3 Bedroom and 3 Bath condo located in the resort community of Beachplace Association. Faces the golf course and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. End unit with lots of light in the living space ...
Key Amenities
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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 ...
Key Amenities
About this property
2 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course with limited Gulf view and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. All NEW furnishings throughout ...
Distance to beach: 0.3 miles to Gulf Of Mexico
Key Amenities
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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 ...
Key Amenities
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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 ...
Distance to beach: 0.1 miles to Private beach
Key Amenities
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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, ...
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
Beautiful, peaceful one bedroom / one bath condo on Longboat Key. Amazing view and breeze from the lanai. Private friendly gated community with great amenities. Four pools, tennis court, BBQ girls, shuffleboard, work out facilities, game room. Private beach access across the street with private bathrooms ...
Key Amenities
About this property
Come enjoy the Beach - Private parking included. Beautiful beachfront unit on the 3rd floor with a Beach and Lake view. Beachplace Building 3 unit 304. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. A beautiful unit with shiplap wall in living room and master bedroom, great flooring ...
Key Amenities
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Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades.The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs ...
Key Amenities
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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 ...
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
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 ...
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
