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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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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...
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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...
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This 7th floor Islander Club condo was completely rebuilt in 2016 by the project of renowned Boston designer. Modern kitchen with stainless steel brand new appliances opens to spacious living room/dining area with oversized sofa and 55-inch HDTV. Master bedroom with king size bed offers beautiful view...
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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...
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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...
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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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3 Bedroom and 2 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...
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Stunning angled Beach View and Sunset view. This home located in the sought after Seaplace community has a very personal feel to it and has a balcony with a side view that highlights the Gulf of Mexico. This unit is perfect for a person or couple that wants to enjoy the beach and pool and stay in a friendly...
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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,...
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Sought after beachfront unit on the 5th floor of building 9 and an end unit. 2 bedroom, 2 bath unit with stunning views and very well appointing furnishings.Beachplace is one of Longboat Key's premier vacation rental locations on the island!Amazing Gulf Views and private parking.This...
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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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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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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....
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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
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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...
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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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Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and...
Distance to beach: 100 yards to Whitney Beach
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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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**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...
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Spacious 2 bedroom condo in Beachplace gated complex. King in Master 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...
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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...
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This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity that comes along seldom. This impressive home is your rental opportunity to live your best life and indulge in the finer things. As you step inside, prepare to be awestruck by the stunning...
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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...
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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...
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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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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...
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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...
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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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...
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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-
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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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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...
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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....
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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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...
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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...
Distance to beach: 0.0 miles to Whitney Beach
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Step into coastal luxury with this beautifully renovated, ground-floor 1-bedroom condo mere steps from the sparkling shoreline of Longboat Key. From the moment you enter, the panoramic beach view draws you in like a wave—open the sliding glass doors to feel the gulf breeze, hear the soothing rhythm...
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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...
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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
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
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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ISLAND PARADISE ON LONGBOAT KEY. This 3 bedroom, 3 bath home sits just 300 feet of the sugary white sands on Beer Can Island, located on Longboat Key. Walk down to the beach, or hang out on the lanai, playing ping pong or use the semi private pool located with an entrance located just steps from the back...
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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...
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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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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
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 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
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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...
Key Amenities
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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....
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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