Home Vacation Rentals By Owner In Longboat Key, FL

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$318.88

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Arbomar 302 Gulf Front 2 BR by FVC

Longboat Key, Florida, United States

Beachfront Bliss on Longboat Key – Stunning Views & Modern Comfort brbrStay directly on the beach in this beautifully updated getaway, perfectly situated mid-island on Longboat Key. Wake up to breathtaking Gulf views, soak in vibrant sunsets from the living area, both bedrooms, and the open terrace, and enjoy the ultimate beachside retreat. brbrThis condo is professionally managed by Florida Vacation Connection, a trusted local company with over 25 years of experience on Longboat Key. brbrInside, the kitchen has been completely renovated with sleek quartz countertops and brand-new GE Profile appliances—a stunning space to prepare meals. Both bathrooms have been elegantly updated, and the living room features all-new furniture, a flat-screen TV, a DVD player, and WiFi for your convenience. Each bedroom also has a flat-screen TV for your entertainment. brbrStep outside and unwind by the resort-style beachfront pool, featuring a newly renovated deck and patio—just steps from the sand. Whether you're basking in the Florida sunshine or taking a dip in the Gulf, this is the perfect place to relax and recharge. brbrArbomar offers fantastic community amenities, including a fitness center, grilling area, a recreation clubhouse, elevators, and a 24-hour secured building. brbrBeyond the beach, you’ll have easy access to world-class dining, boutique shopping, and the vibrant arts and culture of downtown Sarasota. brbrNo matter the season, this beachfront haven is ready to welcome you. Come and experience the best of Longboat Key! brbrTown of Longboat Key RRR.00204.2023
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Exceptional(38)

$228.93

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Upscale Beachplace Condo...availability starting in May 2026....please inquire

Longboat Key, Florida, United States

LATEST NEWSFLASH FOR BEACHPLACE UNIT 4-404: br* 2025 and Winter season 2026 have been fully booked. First available dates start May 1, 2026. Please inquire for special discounts offered May - Nov 2026. brbr* Winter months (Dec-April) for any year are not available for booking online....sorry.brbr* For your safety, we continue to follow COVID cleaning and safety protocols as established by the American Hotels & Lodging AssociationbrbrALLOW US TO HOST YOU AND YOUR FAMILY FOR A BEACH HOLIDAY:brThis beautifully furnished beachfront condo on Longboat Key, Florida is the largest 2 bedroom unit available in the Beachplace complex...over 1500 sqft. We recently completed a total window replacement project, installing new windows and doorwalls throughout the unit. The views are spectacular....few rental units have this added luxury. We also upgraded the entertainment system in the living room with 60 wall-mounted Sony TV and soundbar....great for movies and sports. Xfinity cable box allows you to log into your Netflix or Amazon Prime accounts and also has DVR service. brbrThis two bedroom/two full bath condo was totally remodeled and renovated, floor to ceiling. It was gutted down to the cement frame and rebuilt with premium, high-end features (more details below). If you value cleanliness, this condo is immaculate....please see my guest reviews. Beachplace is very popular in the summer with European and Canadian vacationers with many families returning year after year.brbrLocated on Florida's Gulf Coast just across the bay from downtown Sarasota, this luxury unit is in the Beachplace complex (building 4, 4th floor) at the south end of Longboat Key. As an exclusive premium gated community, Beachplace has all the amenities including a large heated pool, hot tub spa, tennis courts, exercise gym, clubhouse, walking paths, wireless internet, and much more. But the real reason to come here is the private beach -- 9 miles of sugar white sand, crystal clear water, and plenty of peace and quiet. Stroll for hours, swim in 85+ degree water in the summer, hunt for exquisite sea shells, or fish from the local pier. brbrThis unit offers a King bed master suite, and two twin beds in second bedroom, large screen HDTVs, DVD players, wireless internet, all linens, dishes, etc provided. Washer and dryer are in the unit. The unit is 'turn key' - everything you need is there including fishing and tennis gear. Also there is a spacious furnished patio with views of the Gulf of Mexico to the right, and Sarasota Bay to the left. Enjoy spectacular sunrises or sunsets!brbrThe unit is located on the 4th floor (of 6) and is over 1500 square feet with covered parking included. Our renovation included completely gutting the unit down to the cement frame and modernizing everything with high-end features. Here are some highlights:br• New HVAC system in 2019, includes an ultraviolet disinfection system that kills airborne viruses and bacteria in the air. br• Beautiful kitchen with custom premium cherry cabinets, Brazilian granite counters and backsplash, stainless steel appliances, and porcelain tile floor br• New (2024) LG front loading washer and dryer in unitbr• Hardwood floors throughout - Amendiom Brazilian oak harvested under the principles of sustainable forest managementbr• Master bath with custom-built walnut spa vanity, Brazilian granite top, two graphite vessel sinks, charcoal porcelain tile, multi-head shower with stone tile surround and clear glass enclosure.br• Guest bath with custom-built cherry vanity, Brazilian granite top, patterned glass vessel sink, porcelain tile, Jacuzzi tub / shower with stone tile surround, custom glass sliding door.br• Open design and layout - removed walls, raised ceilings, created an open and bright floorplanbr• Bright lighting throughout with dimmersbr• Casablanca ceiling fans in both bedrooms, absolutely silent with infinitely variable speedsbr• Hunter-Douglas window treatmentsbr• New high-definition flat screen TVs (Sony) and Xfinity cable. On demand options plus access to Netflix, YouTube, Prime Video and more. brbrbrRates are shown below: brbrRATE INFORMATION (per month based on 28 nights.....not including taxes fees):br 2025 2026brJanuary - March............ $ 12300 $ 12500brApril & Dec......................$ 7200 $ 7300brMay - November........... $ 4950 $ 4950brbrAll rentals subject to $165 application fee, $200 cleaning fee & 13% state & local taxesbrbrDiscounts for 3 or more month rentals.....inquire for special quotes.brbr* Summer holiday vacationers from UK, mainland Europe, and Canada receive a special treat. Inquire for details.
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$243.55

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Beachplace Living – Walk to Beach, Swim, Play & Unwind #11-303 Condo by RVA

Longboat Key, Florida, United States

RVA offers this comfortably appointed two-bedroom, two-bathroom condominium in the desirable gated community of Beachplace. Located on the Southern end of the property, at unit 11-303 you'll enjoy golf course views and warm Florida breezes from your private open-air patio - the two main ingredients needed for a true Florida getaway. Indulge in an array of amenities designed to enhance your stay and elevate your experience. From community beach access to a fitness facility, from tennis courts to a community pool, every aspect of leisure and recreation is meticulously catered to. brbrbrbrInside your unit, discover the convenience and comfort of a full-size kitchen, a washer/dryer for added convenience, assigned outdoor parking, wireless internet access to stay connected, and all the club amenities featured by Beachplace. Call today and ask for Beachplace 11-303.brbrbrbrAccommodations: Two-bedroom, two-bathroombrbrbrbrAmenities: Community Beach Access, Elevator, Private Deck, Grill, Community Hot Tub, Community Pool, Fitness Facility, Locker Rooms with Sauna, Full-size Kitchen, Tennis Courts, Washer/Dryer, Private Location, Wireless Internet AccessbrbrbrbrLocation: 1085 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 Queen, 2 TwinsbrbrbrbrView: Golf Course ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $165 Fee + Application; $25 Cancellation Penalty
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$581.38

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Private Vacation Home

Longboat Key Waterfront: Private Heated Pool w/ Soaking End & Luxury Hot Tub!

Longboat Key, Florida, United States

Newly renovated, this beautiful home features a split floor plan with generously sized bedrooms and walk-in closets, all enhanced by a charming coastal flair. The kitchen—truly the heart of the home—is fully equipped with everything you need to prepare delicious home-cooked meals. Enjoy your morning coffee or an evening cocktail in the cozy coffee-bar area.brbrStep outside to the brand-new pool and spa. One end offers a shallow sun-shelf perfect for soaking or sunbathing before you slip into the refreshing deep end. The expansive stone pool deck provides plenty of space to relax on the lounge chairs and soak up the Florida sunshine.brbrWelcome to peaceful Buttonwood Harbour, a community of just 50 homes located in one of Longboat Key’s most established and desirable neighborhoods. Perfectly situated in the center of the island, you’ll be within walking distance to Publix, the Shoppes of Bay Isles, tennis courts, the post office, and CVS. The neighborhood is known for its friendly atmosphere and natural beauty, making it a favorite for outdoor enthusiasts.brbrBoaters and fishermen will appreciate access to the BHA boat ramp, the ability to dock a boat at the home during your stay, and available kayak storage if you choose to rent them. With no bridges between Buttonwood Harbour and the open waters of Sarasota Bay, getting out on the water is easy. Bayfront Park is just 1.4 miles away and offers a 1,350-square-foot indoor recreation center, playground, basketball court, shuffleboard, multipurpose open field, three dedicated pickleball courts, a tennis court, picnic areas, restrooms, and convenient parking for the public beach access across the street. There`s also a dog park for your furry companions.brThere must be a minimum of (2) adults overbrthe age of 30 as named tenants. We do not lease to young adults without adults over the age of 30 on the premises.brbrRefundable damage deposit of $2000
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Exceptional(80)

$754.65

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Luxurious Beachfront Jr. Suite by FVC

Longboat Key, Florida, United States

Proudly offered by Florida Vacation Connection, this beautifully updated 650-square-foot Beachfront Jr. Suite is your ticket to paradise on Longboat Key.brbrWake up to the soothing sound of waves and panoramic views of the turquoise Gulf waters right from your bed. Step onto your private lanai to sip morning coffee, watch dolphins play, or enjoy al fresco dining as the sun sets over the horizon.brbrInside, every detail has been designed for both comfort and style. The King-sized bed is dressed in soft coastal linens and fluffy pillows. Updated vanities, spacious closets, and floor-to-ceiling mirrors add a touch of elegance and function to the dressing area, while a safe provides peace of mind for your valuables. The bathroom offers a spa-like retreat with Italian porcelain tile and an onyx-inlaid tub and shower.brbrThe fully equipped kitchen is as functional as it is beautiful, featuring sleek cabinetry, granite countertops, stainless-steel appliances, and stylish lighting. Dine indoors at the granite table for four or step out to the lanai, where a second dining table and a chaise lounge invite you to relax and unwind.brbrStay connected—or unplug completely. A 55” smart TV with cable, complimentary Netflix, high-speed secured Wi-Fi, and web TV options are included. Additional conveniences such as a copier/printer, washer and dryer, ceiling and table fans, hair dryer, iron, and ironing board ensure a seamless stay.brbrWhile resort amenities such as golf, dining, tennis, fitness center, and room service are reserved exclusively for resort guests, our renters enjoy access to the stunning private beach, pool, and hot tub area—all at a significantly reduced rate compared to booking directly with the resort.brbrPlease note: No transactions take place on property, with the exception of beach umbrella rentals available through the Concierge.brbrLocated behind the gates at the coveted southern tip of Longboat Key, the suite offers a peaceful and prestigious setting—just a short drive to the vibrant shops and restaurants of St. Armands Circle and the cultural delights of downtown Sarasota.brbrSorry, no pets permitted.brbrCome experience the charm and elegance of this Beachfront Jr. Suite and discover the special magic of Longboat Key.brbrTown of Longboat Key RRR-00140.2023
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Exceptional(13)

$468.57

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Wonderful beach condo, heated pool, peaceful location Longboat Key

Longboat Key, Florida, United States

On the beach! Wonderful 2 BR condo brThis large and airy 2 bedroom condo is right on the beach. It is a corner unit on the ground floor and it is very private and peaceful. No stairs - just step right outside. The ideal spot for a relaxing getaway and memorable sunsets. brbrThis easy access ground floor unit offers two-bedrooms, two-bathrooms, a spacious living room, a full-size kitchen, washer/dryer and a private lanai. brbrThe master bedroom has a king size bed and a queen bed. Flat screen tv. The second bedroom has a queen size bed. Free wireless high speed internet and cable. Linens and towels are provided. This roomy condo is 1 600 sq. ft. or 150 m2.brbrYour private lanais overlooks the turquoise waters of the Gulf of Mexico. The long white sandy beach is just steps away. Chaise lounge chairs available for your convenience. There is a heated pool and tennis/pickle ball courts. Beautiful grounds with tiki huts, barbeque and shuffle board. Bike path along the entire length of Longboat Key. Close by you have Bay front park with open play pickle ball courts.brbrGreat restaurants and shopping nearby. Across the street you'll find Whitney plaza. A quaint little plaza with several places to eat, a bar, a liquor store, a hair salon, a 24 h gym, pilates studio, a kayak and stand up paddle board rental, a design gift store, and more.brbrThe barrier isle Longboat Key has been voted one of North America’s top islands by Condé Nast Traveler’s readers. Whitney Beach is located on the north end of the island. brbrApproximately 15-30 minutes from downtown Sarasota and the famous St. Armand’s Circle with restaurants, shopping and culture. brbrLongboat Key is your perfect paradise. brbrThere are activities and attractions for all age groups. Fishing, boating, jet skiing, para sailing, kayaking, biking, golf, tennis, snorkling, scuba, shelling, turtle watching and much more…brbrMote Aquarium, St. Armand’s Circle, Marie Selby Botanical Gardens, Van Wezel Performing Arts Hall, John and Mable Ringling Museum and Salvador Dali Museum. Busch Gardens in Tampa and only a two-hour drive to Orlando's theme parks.brbr30 minutes from Sarasota-Bradenton Airport and about an hour and a half from Tampa International.brbrWelcome to truly paradise on exclusive Whitney Beach, Longboat Key!brbrOccupancy and rate may be for less than 30 days.brbrAdjacent 1 BR condo also available for rent. Please see VRBO Listing # 682995brbrWhether you're seeking a peaceful escape or an adventure-filled getaway, our beachfront condo offers the perfect blend of comfort and convenience. Indulge in the beauty of Longboat Key and create lasting memories during your stay.
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$314.49

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Private Vacation Home

Tennis & Beach Retreat – Cedars East #804 by RVA

Longboat Key, Florida, United States

Escape to Paradise at Cedars East Tennis Resort – Longboat Key Luxury Townhome by RVA Resort VacationsbrbrbrbrWelcome to Cedars East Tennis Resort, your exclusive Longboat Key vacation destination by RVA Resort Vacations. Nestled along Florida’s stunning Gulf Coast, this luxury townhome resort offers the perfect balance of relaxation, recreation, and refined comfort. Whether you’re here for a romantic getaway, a family vacation, or a tennis-filled retreat, Cedars East invites you to experience the best of coastal living on Longboat Key.brbrbrbrStep inside your spacious, fully furnished vacation townhome, thoughtfully designed for both style and comfort. Each residence features bright, open living spaces with coastal-inspired décor, a full-size kitchen with breakfast bar, a separate dining area, and—available in select units—a private screened lanai for morning coffee or evening sunsets.brbrbrbrEvery detail has been curated to make your stay effortless, from modern appliances and wireless internet to plush bedding and private parking. Discover your Longboat Key getaway at Cedars East Tennis Resort Unit #804, a luxurious 2-bedroom, 2.5-bathroom townhome tucked away in the exclusive Preserves area. Enjoy the perfect mix of Gulf Coast serenity, modern comfort, and resort-style amenities—designed for both relaxation and recreation.brbrbrbrBedroom Details:brRelax in comfort with thoughtfully designed sleeping arrangements ideal for families or couples. Master Bedroom: Features a plush King bed with premium linens, offering the perfect retreat after a day of sun and island adventure. Second Bedroom: Includes two comfortable Twin beds, ideal for children or additional guests.brbrEach bedroom is tastefully furnished with coastal décor and ample storage, creating a serene and restful atmosphere during your Longboat Key getaway.brbrbrbrResort Amenities That Redefine Relaxation - At Cedars East Tennis Resort, every day feels like a vacation. Enjoy access to a full suite of resort amenities designed to inspire activity, leisure, and connection.brbrbrbrTennis and Pickleball Courts – Play on 10 Har-Tru (soft-clay) courts, with access to professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts are also available.brbrbrbrPro-Shop – On-site shop offering tennis and pickleball gear, apparel, and help with court reservations.brbrbrbrJunior Olympic-Sized Heated Pool – Relax or swim laps in the resort’s expansive heated pool, complete with complimentary chaise lounges and a seasonal Tiki Bar.brbrbrbrFitness Center – Work out anytime in the modern 24-hour fitness facility with secure access.brbrbrbrBicycles for Guests – Complimentary adult-sized bikes are available for exploring the scenic Gulf of Mexico Drive and nearby attractions.brbrbrbrHugo II Restaurant – A seasonal European Fusion dining experience featuring German, Czech, and Italian-inspired dishes with specialty Prosecco cocktails. Private dining memberships are included for Cedars Club guests.brbrbrClubhouse and Social Spaces – Enjoy social gatherings in the Clubroom and bar area, or relax in cozy communal lounges.brbrbrbrFishing Pier and Mangrove Boardwalks – Stroll along charming boardwalks through the mangroves leading to a serene fishing pier, ideal for picnics, watching marine life, or taking in sunset views.brbrbrbrBeach Access and Island Adventures - The Gulf of Mexico shoreline stretches endlessly along Longboat Key, offering soft sand and sparkling turquoise waters. Guests of Cedars East are welcome to enjoy the beach via designated Public Beach Access points clearly marked along Gulf of Mexico Drive.brbrFor even more adventure, take a short drive to St. Armands Circle and downtown Sarasota for fine dining, boutique shopping, art galleries, and live entertainment.brbrbrbrAmenities: Wireless Internet, Full-Size Kitchen, Private Lanai, 1-Car GaragebrbrbrbrLocation: 804 Evergreen Way, Longboat Key, FL 34228brbrbrbrView: Garden and Partial Bay ViewsbrbrbrbrWhether you’re here for the world-class tennis, resort amenities, or simply the peaceful coastal ambiance, Cedars East Tennis Resort by RVA Resort Vacations offers everything you need for a luxury Gulf Coast escape.brbrbrbrBook your stay today and discover why Cedars East remains one of the most sought-after Longboat Key vacation resorts on Florida’s Gulf Coast.brbrbrbrMinimum stay requirements apply
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$163.47

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Beachview 2 BR / 2 BA Beachplace condo by FVC

Longboat Key, Florida, United States

Beachplace 5-402 | Pond & Beach Views | Florida Vacation ConnectionbrbrWelcome to Beachplace 5-402, your serene getaway on the southern end of Longboat Key! This beautifully appointed 2-bedroom, 2-bath condo offers the perfect blend of coastal comfort and stunning views—overlooking both a peaceful pond and the sparkling Gulf of Mexico.brbrStep inside to a bright, open living space designed for relaxation. The private balcony invites you to unwind with morning coffee or evening cocktails while enjoying gentle sea breezes and picture-perfect sunsets. The fully equipped kitchen makes meal prep a breeze, and the dining area is ideal for both casual breakfasts and family dinners.brbrThe spacious primary suite features a king-sized bed, en-suite bath, and direct access to the lanai—perfect for waking up to tranquil water views. The guest bedroom offers two comfortable twin beds, making this a great option for families or friends traveling together.brbrLocated within the gated community of Beachplace, you'll have access to resort-style amenities including a heated pool and spa, tennis courts, fitness center, clubhouse, and private beach access just steps away.brbrWhether you’re lounging by the pool, strolling along the shoreline, or simply soaking in the views from your balcony, Beachplace 5-402 offers the ideal Longboat Key escape.brbrManaged by Florida Vacation Connection – your local experts in luxury vacation rentals.brTown of Longboat Key RRR-00168.2023
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$631.76

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Sea Grape Inn #1- Beachfront Property

Longboat Key, Florida, United States

BEACH FRONT Condo- 1st Floor of Beach Front Property, 2 BDRM/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. br**Need to stay less than the minimum required nights Send us a message!**brCheck out our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex, located beachside, on the shores of the Gulf of Mexico, on Longboat Key. Sea Grape Inn offers 8 beautiful condos in a beachfront location and personalized service, with amenities that cater to an array of travelers. A perfect beach getaway!brbrBEACH FRONT Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbrUpdated stunning BEACHFRONT condo, boasts the prime location at the complex - located on the 1st floor at the very front of the building with the closest direct beach access. brbrThe unit has recently been updated with all the modern conveniences of home, in a luxury vacation rental. The living room area has a flat screen TV, two sofas (1 sofa bed), and updated decor. An expansive screened-in lanai virtually doubles the living space of this condo, complete with a comfortable teak patio table and a seating area - with gorgeous front-row views of the ocean and breath-taking sunsets. The primary suite offers a king bed, flat screen TV, and updated private bathroom. The second bedroom suite has two twin beds, a flat screen TV and an updated private bathroom. brbrCasual elegance in a tropical setting - make this unit your home for your next beach getaway! brbrThe Following *Required Fees are included in the total cost.br*Required $150 Departure Cleaning Fee. brbr*Required Conservation Fee of $10 per night will be charged due to Longboat Key Ordinances to protect Turtles.brbr*Required Damage/liability insurance fee $70 is mandatory and will cover any damages or missing items in the guest rental unit or property, as needed. This damage/liability enables The Sea Grape Inn to rent to guests without requiring a refundable damage deposit. brbrCANCELLATION POLICY:br~Cancel 91 days or more prior to arrival date, guest will receive a full refund less a $250 admin fee.br br~Cancel 31-90 days prior to arrival receive full reservation credit for a future booking valid for 1 year (less any booking fees). Original reservation pricing is not guaranteed. Guest will be required to pay the difference if there is a price increase for new booking dates.br br~Cancel 30 days or less prior to arrival, or a N0-Show; No Refund Or Booking Credit will be provided.brSee house manual in rental
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$318.55

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Float Above The Waves In Paradise - Beach Front, 2 Bed, 2 Bath

Longboat Key, Florida, United States

brPlease DO NOT try to book this property initially as there is an approval process including a background check which can take about a week. Simply Ask Owner A Question first, then once approved we can go to the Request to Book stage. brbrTake advantage of the beach at your back door and enjoy this stunning vacation condominium with spectacular views of the Gulf of Mexico, located on Longboat Key- an extraordinary 11 mile barrier island along the coast of Sarasota, Florida. brbrOur beautiful 7th floor condo has two spacious bedrooms and two bathrooms in the highly sought after Islander Club and provides you with full Gulf views from every room! The outdoor patio is the length of the entire condominium and ideal for enjoying outdoor dining, warm Gulf breezes and the most unforgettable sunsets. From the 85 foot balcony, enjoy panoramic views that include downtown Sarasota all the way to Siesta Key.brbrThe living room combines with the dining area to provide an expansive open living space, including a pull out sofa for guests. Fall asleep listening to the mesmerizing sound of the surf from the spacious master suite which includes a king sized bed, large walk-in closet and private bath. The spacious and bright guest bedroom offers one queen and one twin bed, plenty of closet space and stunning beach and water views.brbrSituated on the south end of the Key, the Islander Club is just steps from the water's edge. Location, location, location! 4 miles from St. Armand's Circle, directly across from the Long Boat Key Club Golf Course and walking distance to the new Publix and CVS. During the day, utilize private beach access to swim in the Gulf or to fish off the pier. You can also enjoy lounging on the grand waterfront patio which offers a beautiful swimming pool. Your stay includes access to spectacular amenities at the Islander Club including an Olympic-sized heated pool, sauna, Har Tru tennis courts, library, billiard room, recreation room, Gulf front fitness room, secured lobby and on-site management.brbrThis barrier island is filled with beaches, boating, water sports, tennis, and two championship golf courses located at the Longboat Key Club. The Islander is conveniently near St. Armand's Circle and downtown Sarasota where you will find an abundance of upscale shops, fine dining and attractions, including museums, art galleries, entertainment and cultural activities.brbrThis island paradise could provide the perfect setting for your tranquil beach vacation year after year.brbrSTRICTLY No Smoking ANYWHERE in the Islander Property. No pets allowed in the building.brbr90 Day Minimum brbrSubject to Owner/HOA Board Approval. Rental subject to minimum lease requirements.brbrhttps://my.matterport.com/models/FCtcagccoZF cta_origin=last_created_space&organization=q16XknXHLAZ
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Home Most popular vacation rentals in Longboat Key