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
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. ...
Property Type
Longboat Key Condo
Key Amenities
About this property
60 Day Minimum Required. Beachfront Condo offers great views to the gulf from the 7th floor living room and bedroom. This unit is freshly remodeled. Enjoy the oversized balcony with two ceiling fans as you relax and watch the full beauty of nature.Association requires a minimum of 60 days. Direct ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
Beautiful beachfront 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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
You will be captivated by the majestic ocean views the moment you step foot into the unit. Step out of this 1st floor unit and in just over 100 steps you be dipping your toes in the water. Whitney beach is pristine and private with wonderful people who own and rent. Enjoy the beachside pool and 4 ...
Property Type
Longboat Key Condo
Featured review
Wonderful. Great location. Great facilities. Well equipped. Wonderful for families. Beach is gorgeous.
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Distance to beach: 5 feet to Just outside your door & window
Key Amenities
About this property
Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful!No need to fight any traffic or an overcrowded public beach. Beautiful view of the turquoise waters of the Gulf of Mexico. It is very private and peaceful. The ideal spot for a relaxing getaway ...
Property Type
Longboat Key Condo
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 ...
Distance to beach: 150 yards to Gulf Of Mexico
Key Amenities
About this property
Ground Floor Villa Condo- 1 Bedroom- Sleeps 2 - walk 4 min to beachBeautiful end unit attached villa in the charming walkable community of St. Judes on Longboat Key. Just a short 4 minute walk to the private beach access and a 3 minute walk to the 32 acre Joan Durante Park FULL of fabulous tropical ...
Property Type
Longboat Key Villa
Featured review
This place was clean and had everything you would need. The bed was the most comfortable bed I have ever slept in. The beautiful beach was just a short walk away and they provided beach chairs too. The ...
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
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
About this property
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 ...
Property Type
Longboat Key Villa
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 ...
Distance to beach: 0.1 miles to Across Gulf of Mexico Dr
Key Amenities
About this property
TOTAL FULL DIRECT BAY VIEW in the front and Canal view in the back!!!! This 2 BR 2 BATH comfortable coastal beachy condo will delight and impress both inside and out. The primary bedroom has a king bed and en-suite and the 2nd bedroom has a queen size bed. Previous reviews have all been 5 star on other ...
Property Type
Longboat Key Condo
Key Amenities
About this property
Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for ...
Property Type
Longboat Key House
Key Amenities
About this property
Nestled in a serene enclave, this charming one-bedroom cottage is the perfect island oasis. Combining timeless elegance with modern amenities, it features high vaulted ceilings, a contemporary kitchen, & cutting-edge conveniences including high-speed internet, a reverse osmosis water system, & ...
Property Type
Longboat Key Cottage
Featured review
We had an unforgettable time in Longboat Key! The cottage we stayed in was perfect for what we were looking for. It’s located directly in between the bay and the gulf where we could easily walk from ...
Key Amenities
About this property
Last minute fall getaway special!Just a short 0.3-mile stroll to Whitney Beach! This charmingly renovated cottage is tucked away in the back corner of a spacious, gated lot. Ideal for a romantic getaway for two: queen Tempurpedic sofa (no uncomfortable mattress bars!) and a cozy daybed to also accommodate ...
Property Type
Longboat Key Cottage
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: 500 feet to Private access
Key Amenities
About this property
Private BEACH Access! [2 Units Available Turquoise Gem and Turtle Walk CONTACT ME Turtle Walk MAY BE AVAILABLE] *Designer Renovation* Single level, 4 minute Walk to Bright White Quartz Sand, Welcome to UPGRADED BEACH PARADISE Featuring - NEW Full Stainless-Steel Kitchen, NEW Cabinets and Granite Countertops. ...
Property Type
Longboat Key Apartment
Key Amenities
About this property
We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and walk trails and bay lookouts nearby. EASY ACCESS VIA a new, fully enclosed ELEVATOR, beside the GARAGE TO ALL THE LIVING AREAS! Over an acre of lawns joining to 35 acres of park ...
Property Type
Longboat Key House
Distance to beach: 0.2 miles to Whitney Beach
Key Amenities
About this property
3 bedroom, 2 bath cottage close to Gulf and Bay Great 3 bedroom, 2 bath house with pool on the north end of Longboat Key. Longbeach Village is a neighborhood with 'Old Florida Charm' unlike most of LBK. You will be two houses from the bay (boat launch and pier), and 3 blocks from a fabulous ...
Property Type
Longboat Key House
Key Amenities
About this property
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 ...
Property Type
Longboat Key Condo
Featured review
Lovely place with a great view of the bay. Well set up with all of the things you need. Owner very accomodating
Key Amenities
About this property
Newly renovated 3 bedroom, 2 bath condo. Open kitchen, spacious living room and an integrated dining room. Office den, ideal for working or relaxing. Master bedroom features a private balcony to enjoy the ocean and spectacular sunsets. Laundry room with full size washer and dryer. Two oceanfront balconies ...
Property Type
Longboat Key Condo
Key Amenities
About this property
Newly remodeled charming 2 bed/ 1 bath beach condo located 5 min walk from beach, restaurants, groceries and more. Perfect place for a relaxing beach getaway!Nestled in a quiet residential complex and centrally located in Longboat key, condo features a fully equipped renewed kitchen with upgraded ...
Property Type
Longboat Key Villa
Featured review
This is a darling condo, that looks exactly as it is pictured, with all the needed items for cooking and beaching and enjoying a a very relaxing vacation. August is not the best month in Florida but the ...
Key Amenities
About this property
This Spectacular beachfront condo on Longboat Key is a 2 bedroom, 2 bath unit on the 6th floor of the Arbomar Condominium. An open concept floor plan includes a galley kitchen with SubZero appliances, dining room, and living room that exits to a spacious lanai overlooking the Gulf of Mexico. Take in ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Mobile Home
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 ...
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, ...
Property Type
Longboat Key Condo
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. ...
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 ...
Property Type
Longboat Key Townhome
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 ...
Property Type
Longboat Key Apartment
Key Amenities
About this property
Welcome to your amazing beachfront vacation. The apartment has a fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room ...
Property Type
Longboat Key Condo
Key Amenities
About this property
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 ...
Property Type
Longboat Key Apartment
Key Amenities
About this property
Available April 2025. Beautiful, newly remodeled condo with spectacular views of Sarasota Bay and private access to the white sand beaches across the street (few steps away). Second floor, end unit located in Pelican Harbour Condominium and Beach Club in Longboat Key. An extensive remodel was just ...
Property Type
Longboat Key Apartment
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 ...
Property Type
Longboat Key Condo
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 ...
Property Type
Longboat Key Condo
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, ...
Property Type
Longboat Key Condo
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 ...
Property Type
Longboat Key Condo
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 ...
Property Type
Longboat Key House
Featured review
What a location! Walk to beach and local restaurants. Beautiful little cottage! Plan to return in 2024. Love that it pet friendly.
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 ...
Property Type
Longboat Key House
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 ...
Property Type
Longboat Key House
Key Amenities
About this property
Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning JUNE 6, 2024.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 ...
Property Type
Longboat Key Condo
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
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 island ...
Property Type
Longboat Key House
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
***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 furnished with a farmhouse coastal decor offering two bedrooms on the second ...
Property Type
Longboat Key Condo
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. ...
Key Amenities
About this property
Discover a unique, remodeled 1920s bungalow near Whitney Beach and the bay, offering an open layout with high ceilings and modern appliances. This home features a heated pool, hot tub, and lush, private landscaping. Originally a post office, it has historical charm with a fully fenced yard, boat parking. ...
Property Type
Longboat Key House
Featured review
We stayed at this gem for 6 weeks while renovating our home and it was fabulous!!! The location is amazing, literally 3 blocks from Whitney Beach, fabulous dining options literally across the street (Mar ...
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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