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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.
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Beach views from kitchen through living room and master bedroom, 3 bedroom, 2 bathroom condo on beautiful Longboat Key. Second floor unit in 3 floor complex, easy access within complex and beach, walking distance to great dining. Complex complete with pool, beach chairs, barbeque grill and tennis / pickleball...
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Seaplace is a gulf-front community that sits on 42 acres. Enjoy a half mile of beachfront and 1-mile walking trail in addition to two heated pools and three Har-Tru tennis courts.This home located in the sought after Seaplace community has a very personal feel to it and the beach is steps away from...
Key Amenities
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Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows...
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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...
Distance to beach: 100 yards to Whitney Beach
Key Amenities
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Discover this 3-bedroom gem in Longboat Key.Wake up to the sound of waves and enjoy direct beach access just a few feet from your door. This bright and inviting first-floor 3-bedroom, 2-bathroom condo on Longboat Key offers 1,500 square feet of comfort, convenience, and coastal charm, the ideal place...
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Key Amenities
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Beautiful and spacious 2-bedroom, 2-bath beachfront condo on Longboat Key. Sleeps 6. Enjoy direct beach access, beautiful Gulf views and spectacular sunsets. Recently renovated with a fully equipped kitchen, washer/dryer and all. the comforts of home. Relax by the heated pool or spend the day on the beach...
Key Amenities
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3 Bed | 2.5 Bath | 1,662 Sq Ft Manatees, dolphins, pelicans... oh my. Designer renovated bayfront townhouse with private garage. Spectacular views of bay, Ringling Bridge and downtown Sarasota. King-size bed in master bedroom with 2 walk-in closets and a glass enclosed shower that looks out onto Sarasota...
Key Amenities
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Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very rare find.Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Oceanfront views, this top floor unit boasts a double balcony....
Key Amenities
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Updated top-floor 2 Bedroom + Den with a pullout sleeper with stunning water views from nearly every room. Enjoy the private beach just steps away, featuring 750’ of Gulf frontage and renowned sugary white sand. The open concept layout is perfect for coastal vacationing, complemented by two spacious...
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,...
Featured review
Spent a full month and it truly felt like a home away from home. The condo had everything you needed for the beach, umbrellas, beach cart, great beach towels & even kids toys. The kitchen was exceptionally...
Key Amenities
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Experience Coastal Elegance at Beachplace PenthouseWelcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking...
Featured review
Dream island rd -great name ,great place Walk in the door and be greeted by an uninterrupted view of the ocean with cormorants ,pelicans and occasional dolphins playing , resting and feeding . The apartment...
Key Amenities
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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...
Key Amenities
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Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool...
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This is a Walkdown level fully remodeled condo. On the soft white sand beaches of Longboat Key, Beach Place offers 31 luxury acres and 1450 linear feet of beach. Resort Style Amenities include large community pool and exercise facility.New Listing! Perfect beach view elevated walkdown level fully...
Key Amenities
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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...
Key Amenities
About this property
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...
Key Amenities
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Located in a QUIET and relaxing AREA of the ISLAND, our guests love the location, where you can WALK TO the BEACH entrance, some of the island’s best RESTAURANTS, COCKTAIL SPOTS, a MINI MARKET, and even a nearby BIKE SHOP. Our condo has been recently REMODELDED and features BRAND-NEW APPLIANCES,...
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....
Distance to beach: 500 yards to Gulf of Mexico
Key Amenities
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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
We had a wonderful month stay at Little Palm and truly enjoyed our time there. The location was a huge win for us. It was easy to walk to restaurants and the park, and just a quick bike ride to the beach,...
Key Amenities
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NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...
Featured review
Great location on Longboat Key…out of the crowds with great beaches. Windward Bay where this is located, is a lovely larger condominium community with excellent amenities. The pickleball group is awesome....
Key Amenities
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Welcome to Sapphire Palms on the Canal, a beautifully renovated waterfront villa on Longboat Key designed in crisp whites and calming sapphire blues.Natural light fills the open living space, where sliding glass doors frame peaceful canal views and swaying palms. The interior blends clean coastal...
Key Amenities
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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: 0.5 miles to Longboat
Key Amenities
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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....
Key Amenities
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Come enjoy the Beach - Private parking included. Beautiful beachview 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 sought after unit with shiplap wall in living room and master bedroom, great...
Key Amenities
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Charming Sarasota Retreat with pool and putting green in Gulf Gate Welcome to your perfect Sarasota getaway! Nestled in the desirable Gulf Gate neighborhood, 2921 Captiva Dr. offers a relaxing retreat just minutes from world-famous Siesta Key Beach. This beautifully appointed vacation rental features...
Key Amenities
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Beautiful unit on the 5th floor with lake/pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit.The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access...
Key Amenities
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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.
Key Amenities
About this property
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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Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning JUNE 1, 2026.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 and...
Featured review
The property owners are terrific. The apartment was impeccable and met all needs and beyond. Would definitely return
Key Amenities
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**Welcome to our beachfront Longboat Key condo!If you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos...
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...
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...
Key Amenities
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Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible panorama! This luxurious condo offers a king-size master bedroom with stunning bay and skyline views, and a comfortable second bedroom with a queen bed.The open-concept kitchen,...
Key Amenities
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Beautiful beachfront unit on the 2nd floor with lake view and partial Gulf. This is a beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. It just feels like home. It was decorated by Anne Folsom Smith. It has many custom features, including hand crafted furniture, unique kitchen backsplash...
Key Amenities
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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...
Distance to beach: 0.3 miles to Whitney Beach
Key Amenities
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Charming one-bedroom guest house featuring floor-to-ceiling windows, high vaulted ceilings, & an open kitchen. Furnished 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...
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
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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...
Key Amenities
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2 Bedroom and 2 Bath condo located in the resort community of Beachplace. Faces the golf course with limited Gulf view and has access to the boardwalks to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. All NEW furnishings throughout this...
Key Amenities
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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: 400 yards to Gulf Beach - Private Owner Beach Pavilion
Key Amenities
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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...
Key Amenities
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Beautiful renovated condo unit with 3 sleeping rooms, at-home office set-up. New marble flooring t/o, new bathrooms, new interior doors, renovated kitchen with new Quartz counters, built in wine refrigerator, two lighted cabinets, fully stocked with all new stainless appliances, range/oven with built-in...
Key Amenities
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On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.Beautiful beachview unit on the 2nd floor with lake view...
Key Amenities
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Beautiful Beachplace beachfront unit on the 3rd floor spectacular Gulf and beach view. Has brand new windows and doors and is an end unit in building 3 with glass sliding doors on 2 walls of the living room. This is the closest building to the pool. It has 2 parking spaces. One is covered. Beautifully...
Key Amenities
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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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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...
Key Amenities
About this property
2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico....
Key Amenities
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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...
Key Amenities
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Rental located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the...
Key Amenities
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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...
Key Amenities
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Spacious 2 bedroom condo in Beachplace gated complex. King in Primary bedroom. Come enjoy your time at the Beach. This is a great condo for you to call home for a month or more. Condo is meticulously clean and well cared for. Owners have upgraded the furnishings including large smart TV's One month...
Key Amenities
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Beautiful beachfront unit on the 5th floor with lake view and partial Gulf. Beautifully appointed 3 bedroom, 2 bath unit with a real feel of home. King Bed in Master, Queen Bed in 2nd Bedroom and 2 twins in 3rd bedroom.RRR-00586.2023Come stay a month or more! The well-maintained and gorgeous...
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...
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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