Vacation Rentals By Owner In Longboat Key, FL

$182.62

DIRECT Gulf Front view from the 4th floor condo at Tiffany Plaza

Longboat Key, Florida, United States

Looking to work remotely during the summer and fall Why not consider working right on the beach Direct Gulf Front Rental available for August through to November 2023 along with the month of March 2024. Gorgeously renovated custom condo, 2 bedrooms, 2 baths. The renovated kitchen is complete with marble countertops and a wine refrigerator! This beach retreat has everything you need to get away from it all. The master bedroom has king accommodations, closets.The guest room offers queen accommodations with a desk overlooking the Gulf of Mexico. In unit washer/dryer and high speed WI FI complete the picture. You will love sitting on the Lanai overlooking the turquoise waters of the Gulf for morning coffee or sunset cocktails. This stellar location is close to dining, shopping and cultural venues, either north or south! (Two minutes north of Publix). The community amenities include a lovely sheltered heated pool, BBQ grills, club room with ping pong table, lending library. One covered parking space included, and plenty of guest spaces. Bayfront Park is also just a short stroll south and has fitness classes, yoga, tennis and pickleball courts, basketball, playground and is a great place to watch the sunrise!

2

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2

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5

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$478.62

/ Nightly

Private Vacation Home

BOOK NOW - BEAUTIFUL HOME NEAR BEACHES

Longboat Key, Florida, United States

ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighborhood. Enjoy the nearby pristine and serene beach, local park, kayaking and finest restaurants. Perfect for couples looking for privacy in splendid, tropical surroundings with resort style amenities. This immaculate home prefers longer rentals to guests who share a passion for refined taste. Your private oasis features a hot tub, heated pool, elevator, free wifi & garage.

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$556.19

/ Nightly

Condo

Sea Grape Inn #3 - Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. Check our online Reviews!brbr** Need to stay less than the minimum required nights Contact us **brbrThe Sea Grape Inn is a boutique-style resort complex, located 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 VIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbrThis first floor 2 bedroom 2 bath condo has a view of the pool and the Gulf of Mexico from the living area and screened in lanai. There is a flat screen TV in the living room. The kitchen is fully equipped. The primary bedroom suite has been upgraded and includes a view of the water and flat screen TV. The primary bath has also been upgraded with a new vanity, tile, tub and toilet. The guest bedroom offers two single beds, flat screen TV and has its own bath. 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 No-Show; No Refund Or Booking Credit will be provided.brSee house manual in rental

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Sleeps

$232.12

/ Nightly

Condo

Gorgeous Remodeled 2 Bedroom Longboat Key Condo with Stunning Bay Views!

Longboat Key, Florida, United States

Beautiful 2 bedroom/2 bath recently updated condo on Longboat Key looking over stunning Sarasota Bay. Top 3rd floor -with elevator.brLocated on the south end of Longboat Key. 10 minute drive to downtown Sarasota. Only a 4 minute drive to St. Armands Circle and short walk to Dry Dock and Chart House Restaurants. Dedicated covered parking for one vehiclebr2 month Minimum

2

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2

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4

Sleeps

Select Dates for Price

Condo

Arbomar 802 2/2 LBK Condo by FVC

Longboat Key, Florida, United States

Arbomar 802 – Longboat KeybrbrDirect Gulf-Front | Newly Renovated 2-Bedroom CondobrbrWelcome to Arbomar 802, an eighth-floor, direct beachfront condominium offering breathtaking, unobstructed views of the Gulf of Mexico. Currently undergoing a complete renovation, this two-bedroom, two-bath residence will soon unveil a fresh, coastal-modern design perfect for your next Longboat Key getaway.brbrThe open living area will feature all-new furnishings, flooring, and finishes, creating a bright and inviting space to relax and unwind. Large sliding glass doors open to a private balcony overlooking the beach, where you can take in endless sunsets and the soothing sound of the waves.brbrThe primary suite offers a comfortable king bed and en-suite bath, while the guest bedroom includes two twin beds and a second full bath, ideal for family or friends traveling together.brbrLocated Mid-Key, Arbomar places you close to the best of Longboat Key, just minutes from the island’s shops and dining, and a short drive to St. Armands Circle and downtown Sarasota.brbrGuests of Arbomar enjoy a heated beachfront pool, private beach access, a fitness center, and a welcoming community atmosphere.brbrPhotos coming soon!brBe among the first to stay in this beautifully updated Gulf-front retreat, professionally managed by Florida Vacation Connection

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Sleeps

$264.51

/ Nightly

Condo

Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach

Longboat Key, Florida, United States

We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!br100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.brbrExperience 24/7 Live Customer ServicebrPrivate Beach AccessbrHeated PoolbrbrA Bayside tennis and residential community in the heart of Longboat Key, FL.brSunshine and warm breezes accent the well-appointed tri-level townhouses that surround Cedars Tennis Resort & Club. Some of our residents are full-time, some are seasonal, and some are even vacationers looking for a private getaway in paradise. Whatever your Longboat Key needs Cedars has a Club amenity or accommodation to meet it. One of the only full-service Clubs on the exclusive barrier island to Cultural Capital on Florida's West Coast, Sarasota, at Cedars you can enjoy the best of both worlds - a private island setting just a short drive to world-class activities. brbrEach unit in this village-like community has a spacious living area, a fully equipped kitchen with breakfast bar and a dining area. Most units feature a screened private patio that adjoins the living area – creating an open, airy feel where Florida breezes can flow freely. One- two- or three-bedroom townhouses are available for residence or rental and can accommodate a couple looking for a quiet getaway, or an entire family with spacious comfort.brbrEach townhouse is privately owned and therefore individual offerings and decor may vary - please visit our VACATION RENTALS page for specific unit rental details.brbr10 Har-Tru Tennis CourtsbrOur Club is proud to offer a selection of tennis amenities including professional instruction, daily clinics, round robins, seasonal tournaments and more - all on our soft-clay courts.brbrJr. Olympic Swimming PoolbrOur members and guests can enjoy our heated, Jr. Olympic sizes swimming pool complete with complimentary chaise lounge chairs and a seasonal Tiki Bar.brbr24/7 Fitness CenterbrA highlight for many of our members and guests, the Cedars fitness center is accessible 24/7 with secure access and modern equipment.brbrBicyclesbrNo matter the time of year, Longboat Key is a bicycle town. Gulf of Mexico Drive is often frequented with bikes of all kinds from beach-going families to competition cyclists. Cedars offers a selection of adult-sized bikes available to Members and guests (fees may apply) for daily use with advanced reservations.brbrMembers CenterbrThe Cedars Members Center is a relaxing place for Members and their guests to retreat after a rigorous match. Featuring coffee, lite bites, board games, a selection of books and TV’s - it is the perfect retreat. The Members Center is also available as a meeting space with advanced reservations.brbrPro ShopbrOur Pro Shop is open daily for tennis reservations and assistance and includes a selection of apparel and outdoor necessities.brbrSEASONAL Tiki BarbrThe Cedars Poolside Tiki Bar is open seasonally and is a great place to unwind at the end of the day, grab a drink and visit with local friends.brbrFishing PierbrStroll to the back of our community where the blue waters of Sarasota Bay reside. Our community fishing pier is complete with picnic tables for relaxing and plenty of fish for catching.brbrWooden BoardwalksbrCedars is broken up into three sections, the 500’s the 600’s and the 800’s, that connect through idyllic wooden boardwalks woven through picturesque mangroves. At night when the lanterns are lit it is a sight to behold.brbrWhat’s included in my stay brbr*With our continued desire to provide a superior guest experience, we offer all our guests a professional linen service which includes freshly laundered sheets, pillowcases, bath towels, hand towels, beach towels, washcloths, dishcloths, and bath mats.*brbrKITCHEN AND LAUNDRYbr• Spongebr• Dishwasher Tabletsbr• Dish Soapbr• Kitchen Cleaning Wipesbr• Laundry TabletsbrFULL BATHbr• Shampoobr• Conditionerbr• Body Lotionbr• Make-up wipesbr• Massage Body Barbr• Bath SaltsbrOur Lux packaging is made from recycled cardboard with matching tissue paper. Sealed with a Sojo sticker so guests know the products are unused.brSCENTSbr• White tea & coconutbr• Fresh citrusbr• LavenderbrADDITIONAL AMMENITIES br• 2 rolls toilet paper per bathroombr• 2 rolls paper towel per kitchenbr• 1 roll of 3 kitchen trash bagsbr• 1 roll of 5 room trash bagsbrBeach Chairsbr• Beach chairs are provided for every guest. brbrAdd-On Services provided by our Exclusive Concierge Service at a 10% discounted rate for all guests of Anna Maria Island Beach Rentals!brbr• Golf Cart Rentalsbr• Bike Rentalsbr• Kayak Rentalsbr• Paddle Board Rentalsbr• Beach Wagon Rentals br• Canopy Rentals br• Beach Toys Rentals br• Beach Cooler Rentals br• Children’s Life Jackets Rentals br• Corn Hole Rentals br• Skim Board Rentalsbr• Beach Cart Rentals br• Beach Wheelchair Rentals br• Crib rentalsbr• Highchair Rentals br• Child Safety Gate br• Children’s Car Seat Rentals br• Pack N’ Playbr• And more!

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$199.96

/ Nightly

Private Vacation Home

NEW HOUSE BOOK NOW LOW RATES

Longboat Key, Florida, United States

HOUSE HOLDS 8 GUESTS KITCHEN HAS NEW APPLIANCES FULLY EQUIPPED WITH UTENSILS DINING ROOM 4 BEDROOMS brbrROKU TV WITH FREE NETFLIX brbrKNOWN FOR WATER SPORTS, DAYTIME SUNSET CRUISES, BIKE RENTALS, KAYAKS AND MORE brbrFAMOUS DRUM CIRCLE FOR OVER 30 YEARS ON SIESTA KEY BEACH brbrNEW BACKYARD 2 BBQ 1 PROPANE OTHER CHARCOAL IS WITH ORIGINAL DESIGN OF PROPERTY brbrSHOPS AND RESTAURANTS SHORT DRIVE brbrPARK IS DOWN THE STREET FROM PROPERTY, WITHIN WALKING DISTANCE BAY SIDEbrbrLIGHTED BACK YARD FOR NIGHTLY ENJOYMENT brbrHARRYS FINE DINING, GROCERY STORE AND DELI ON SAME BLOCK HAS BEEN THERE FOR 30 YEARS brbrBEACH ACCESS ISA SHORT DRIVE YOU CAN USE ACCESS TO LEFT OT GO OVER BRIDGE AND ENJOY THE BEACH brbrSTREET IS VERY PEACEFUL AND QUITEbrbrRESTURAUNTS ARE WITHIN WALKING OR DRIVING SISTANCE

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Sleeps

$556.5

/ Nightly

Condo

Unit #218 Sand Cay Beach Resort Gulf Front

Longboat Key, Florida, United States

Enjoy this breathtaking Gulf-front, sunny unit with spectacular beach and sunset views.brAccommodation for up to 6 with 2 bedrooms, 2 bathrooms and queen sleeper sofa.brThe open floor plan of living room, dining room, kitchen and den offer full views of the sparkling turquoise water, blue sky and white sandy beach. The unit is newly re-decorated in natural, soothing tones of soft blues and tans that flow from the outside colors of the beach, water and sky that you see from all these rooms. There are new wood floors throughout and no carpet. The private balcony has panoramic views, shade cover and comfortable, new patio furniture. brThe spacious master bedroom feels very private, has beach view, king bed, flat-screen TV, en-suite bathroom with walk-in shower and large closets. Living room has beautiful, new pale blue leather sofas. Kitchen is well-equipped with many new items and beach views. The large utility closet is filled with inflatable beach toys, beach cart, games, puzzles, iron/ironing board, clothes drying rack/clothes pins, folding grocery cart, all for your use and convenience.br• Gulf Front, 2nd Floor (with elevator or stairs) on the beachbr• Fully air-conditioned with newly refurbished system as well as ceiling fansbr• Open Concept, Spacious, Light, Fabulous Views br• Full Kitchen with everything you could needbr• Wi-Fi internet; Blue tooth sound; Cable TV with 3 large, flat screen televisionsbr• Parking includedbr• Heated pool & tennis courtbr• Laundry on-site with free, multiple washer/ dryersbr• BBQ grills available on the property lawns next to the beach areabrWhy this property brThis is the perfect place to relax and recharge. The condo has everything you might need for a getaway— beach umbrellas, towels, coolers, paddle boards, tennis racquets, etc. brThe unit was recently refurbished with new wood floors throughout, beautiful new leather sofas. The fully equipped kitchen has gorgeous views of the gulf.brThe location provides easy access to a superb Publix grocery store, shops, numerous restaurants of all levels on Longboat Key and several beautiful nature parks.brIt's a short drive to St. Armand Circle shops and restaurants as well as downtown Sarasota.

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Sleeps

$241.56

/ Nightly

Condo

Updated, Adorable, Close to Beach and Shops

Longboat Key, Florida, United States

Cozy coastal beach retreat a short walk to the beach and shops.brComfy furnishings, fully equipped kitchen, beach essentials and other amenities.brPrivate backyard with gas grill, patio and outdoor furniture.brWelcome to your coastal oasis on Longboat Key, where relaxation meets sophistication in this beautifully updated 2 bedroom, 2 bath vacation rental just steps away from the pristine shores of the Gulf of Mexico.brAs you step inside, you'll be greeted by the inviting open floor plan, adorned with warm hues of gray, blue, white, and beige, perfectly capturing the essence of coastal living. Sink into the plush comfort of the sectional sofa in the living area, where a large SMART TV awaits for cozy movie nights after a day of beach adventures. Adjacent is the dining area, featuring a charming round glass table and chic bar stools at the kitchen counter, ideal for casual dining or entertaining.brThe kitchen is a chef's delight, boasting granite counters, stainless steel appliances, and crisp white cabinetry, fully stocked with everything you need to whip up delicious meals and refreshing beverages. Whether you're brewing your morning coffee or preparing a gourmet feast, this kitchen has you covered.brRetreat to the primary bedroom, where a sumptuous king-sized bed beckons for a restful night's sleep. Relax and unwind as you catch up on your favorite shows on the flat-screen TV, or take care of business at the convenient desk and chair. The ensuite bathroom offers a touch of luxury with a sleek glass walk-in shower and granite vanity, providing the perfect sanctuary for pampering moments.brThe guest bedroom is equally inviting, featuring another king-sized bed adorned with plush linens and a tall dresser for your belongings. The guest bathroom is appointed with a shower and tub combo, along with a granite vanity and soft towels, ensuring every guest feels pampered and refreshed.brStep through the French doors from the living space onto the enclosed screened-in lanai, where you can soak up the gentle sea breeze and bask in the sunshine. Complete with outdoor furniture and a closet full of beach essentials, this space is perfect for enjoying al fresco meals or simply lounging with a good book.brVenture into the quaint private backyard, where a charming brick patio awaits. Gather around the mosaic stone table and benches for intimate dinners under the stars, fire up the grill for a barbecue feast, or simply relax in the comfortable chairs surrounded by lush local landscaping.brWhether you're seeking adventure or relaxation, this Longboat Key vacation rental offers the perfect blend of comfort and convenience for your coastal getaway. Experience the beauty of the Gulf Coast from your own slice of paradise.brLongboat Key LifebrOnce a vacation land of the Timucuan and Caloosa Indians, Longboat Key is a quieter gulf-side retreat located between Lido Key and Anna Maria Island along Florida's southwest coast. The barrier island is surrounded by the beautiful Gulf of Mexico and Sarasota Bay. The island's eastern shoreline is covered in mangroves with hidden canals and marinas. On the western shoreline, you can walk for miles on the white sandy beaches and swim in the gentle gulf. Imagine spending your days beachcombing, snorkeling, kayaking, paddle boarding, fishing, sailing, golfing, or cycling along the island's winding bike path.brLongboat Key is known for its abundance of dining options. With the Gulf and Sarasota Bay in its backyard, many restaurants focus on serving local, fresh seafood while visitors enjoy amazing waterfront views.brJust south and across the bridge is bustling St. Armand's Circle, a popular destination filled with boutiques, cafes, restaurants and tropical landscaped courtyards. Head north on Longboat Key, cross the Longboat Pass bridge, and find yourself on Bradenton Beach, Anna Maria Island and Holmes Beach. This area offers gorgeous, white sandy beaches, crystal clear water, fun waterfront bars, restaurants and a variety of shops.brbrTown of Longboat Key: RRR-01189.2024

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Sleeps

$777.87

/ Nightly

Private Vacation Home

Luxurious beachfront house on exclusive LONGBOAT KEY. Directly on the beach!

Longboat Key, Florida, United States

This exclusive beachfront house is located on the water's edge, directly on the Gulf of Mexico on sought after Longboat Key. A gem of mid-century modern architecture with a spacious floor plan and vaulted ceilings. When you step onto the rear deck, you walk out onto a pristine private beach and into the warm waters of the Gulf. This modern 4 bedroom, 2 1/2 bath, luxury property has all the amenities, including high end furniture, 4 flat screen TV’s, high speed fiberoptic internet and direct Gulf of Mexico views from nearly every room. brbrThe kitchen is fully equipped, all bedding, linens, towels and beach chairs are provided. This very spacious property is all on one level. A spectacular great room with floor to ceiling sliding glass doors opens up to a large, screened deck and adjacent open outdoor dining area, allowing you to kick back and relax and enjoy gulf front living at its finest. The house's western orientation gives you spectacular sunsets from nearly all rooms, patios and decks.brbrWhat’s better than your own private paradise You are close to all the amenities of Longboat Key, including local restaurants, the Avenue of The Flowers (Publix) shopping center, the Longboat Key tennis center and the Longboat Key Club with its two 18 hole golf courses. If that weren't enough, St. Armand’s Circle, known for its restaurants and boutiques is less than 10 minutes away and downtown Sarasota, with its culture and amenities, is only 15 minutes away! 30 minutes to IMG Academy!brbrMeticulously maintained and one of the only free-standing beach front houses available on Longboat Key.brbrKeywords: Luxury Beachfront House

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Sleeps

$756.06

/ Nightly

Villa

One-of-a-Kind Villa in Beach Castle Direct Views of the Bay, Walk to Beach

Longboat Key, Florida, United States

Hidden gem in Beach Castle Resort on Longboat Key. The only 3 bedroom, 3 bathroom with a two private parking spaces.brDirect bay front views with floor to ceiling windows. Brand new fishing dock with boat slips.brPrivate beach access with loungers, umbrellas, outdoor shower, grill and table to enjoy a sunset meal.brbrEscape to the idyllic shores of Longboat Key and experience the epitome of waterfront luxury at Bayside Hideaway. This exquisite vacation villa is located in the popular Beach Castle Resort. This unparalleled gem offers direct bay front views from numerous rooms within the home, making it a truly unique and one-of-a-kind villa in this small complex. With a two-car garage and a private white picket fenced front area, complete with a charming gate leading to the front door, this villa exudes coastal comfort vibes with its tastefully adorned tropical decor.brUpon stepping into this lavish oasis, you'll be greeted by the spacious interior that boasts not one, but two inviting living rooms and two elegant dining areas, ensuring ample space for relaxation and entertainment. The gourmet kitchen is a chef's dream, featuring modern appliances, sleek countertops, and an open layout, making it perfect for preparing delectable meals while socializing with your guests.brWhat truly sets this villa apart are the floor-to-ceiling windows that adorn the open living area, providing breathtaking views of the lush lawn and the serene waters of Sarasota Bay. These windows not only flood the interior with natural light but also create a seamless connection with the pristine outdoor surroundings.brThe primary bedroom, a secluded sanctuary, occupies the entire second floor. It features a luxurious king-sized bed, a flat-screen TV for late-night entertainment, and an ensuite bathroom that includes a large walk-in shower. The highlight of this room is undoubtedly the panoramic bay front view, allowing guests to wake up to the tranquil beauty of the bay and bask in the glow of morning sunrises.brFor guests on the first floor, two equally inviting rooms await. The first guest room features a comfortable queen-sized bed adorned with plush linens, an ensuite bathroom with a spacious walk-in shower, and direct access to the screened-in lanai. This cozy nook is perfect for sipping your morning coffee or enjoying an evening cocktail while taking in the refreshing bay breeze.brThe second guest room on the first floor is equally delightful, boasting two queen-sized beds, providing ample sleeping space for friends or family. It also offers captivating views of the bay and its own ensuite bathroom, complete with a tub and shower combo, ensuring a relaxing experience for all visitors.brOne of the highlights of the villa is the Mexican-tiled screened-in lanai, where you can unwind in style. Furnished with a large outdoor dining table, comfortable chairs, and sun loungers, it is an excellent spot to savor meals alfresco, bask in the warm Florida sun, or gaze out at the ever-changing bay views. Phenomenal sunrises off the bay paint a daily masterpiece that you can admire from the comfort of your villa.brThis villa's allure extends beyond its opulent interior; it boasts direct access to the resort’s private fishing dock and a convenient gas grill right outside your doorstep. Imagine catching your dinner just steps away from your vacation haven and then grilling it to perfection while watching the evening sky over the bay.brFor those who are water enthusiasts, a boat slip is available, allowing you to explore the surrounding waters at your leisure. Whether you're into fishing or simply cruising along the tranquil bay, the options are endless. In this vacation villa, you have the privilege of experiencing the true essence of beachfront living and savoring the beauty of Longboat Key in unparalleled comfort and style.brAbout Beach Castle ResortbrEscape to the timeless allure of Beach Castle Resort, a family-friendly community nestled on picturesque Longboat Key, offering an enchanting blend of Old Florida charm and modern comfort. The resort boasts a range of accommodation options, including 1 and 2 bedroom condos, and this unique 3 bedroom villa. Each are meticulously designed to provide a cozy and inviting atmosphere for your stay.brImmerse yourself in the essence of relaxation at our community heated pool and hot tub, surrounded by comfortable chairs, umbrellas, and tables, perfect for unwinding under the warm Florida sun. For the active traveler, we offer tennis and pickleball courts to indulge your competitive spirit.brIf you're a fishing enthusiast, our private boat dock with a convenient fishing table awaits your catch of the day. Savor the outdoors with a bayside gas grill, ideal for cookouts, and enjoy your meals at the adjacent table and chairs.brExploration is at your doorstep, with a leisurely stroll to nearby restaurants and shops. And when you're ready for some beachfront bliss, our private beach access welcomes you with sun loungers, umbrellas, and a beachside patio featuring a table, chairs, and a gas grill for seaside picnics. Rinse off the salt and sand in our outdoor shower after a day in the waves.brAt Beach Castle Resort, you have the flexibility to enjoy a short getaway or an extended stay, making it one of the rare resorts that cater to your vacation preferences. Discover a tranquil haven where memories are made and cherished amidst the beauty of Longboat Key's coastline.brLongboat Key Life Once a vacation land of the Timucuan and Caloosa Indians, Longboat Key is a quieter gulf-side retreat located between Lido Key and Anna Maria Island along Florida's southwest coast. The barrier island is surrounded by the beautiful Gulf of Mexico and Sarasota Bay. The island's eastern shoreline is covered in mangroves with hidden canals and marinas. On the western shoreline, you can walk for miles on the white sandy beaches and swim in the gentle gulf. Imagine spending your days beachcombing, snorkeling, kayaking, paddle boarding, fishing, sailing, golfing, or cycling along the island's winding bike path.brLongboat Key is known for its abundance of dining options. With the Gulf and Sarasota Bay in its backyard, many restaurants focus on serving local, fresh seafood while visitors enjoy amazing waterfront views.brJust south and across the bridge is bustling St. Armand's Circle, a popular destination filled with boutiques, cafes, restaurants and tropical landscaped courtyards. Head north on Longboat Key, cross the Longboat Pass bridge, and find yourself on Bradenton Beach, Anna Maria Island and Holmes Beach. This area offers gorgeous, white sandy beaches, crystal clear water, fun waterfront bars, restaurants and a variety of shops.

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Sleeps

$386.46

/ Nightly

Condo

Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

Longboat Key, Florida, United States

Discover Your Dream Escape at Cabana Beach Club Unit 9 on Longboat Key!brbrWelcome to your newly remodeled Gulf-side retreat, perfectly situated in the heart of charming Longboat Key. This lovely unit accommodates up to 5 guests and features 1 bedroom and 1 bathroom, making it an ideal choice for both romantic getaways and family vacations.brbrStep inside to find a fully equipped kitchen complete with modern appliances, a new fridge, and all the cookware and utensils you’ll need to enjoy meals together. The cozy master bedroom boasts a king-size bed, while the living room offers a sleeper sectional and a pullout chair, comfortably sleeping five in total. With linens and towels provided, you can focus on relaxing and enjoying your stay.brbrThe unit is beautifully decorated in a Florida beach theme, creating the perfect ambiance for your coastal escape. Enjoy entertainment with flat-screen smart TVs in both the living room and bedroom, along with high-speed internet and cable access. We also provide a starter supply of essential items, including paper towels, coffee filters, and laundry detergent for your convenience. Washer and dryer located inside.brbrStep outside to enjoy direct beach access, where you can soak up the sun on the soft, white sands or take a dip in the heated pool just steps from your door. For those looking to explore the waters, our boat and fishing dock is available, with rental slips offered at an additional fee.brbrLongboat Key is the crown jewel of the Gulf of Mexico, offering a tranquil setting to unwind and recharge. Go for a leisurely walk along the shoreline, catch breathtaking sunsets, practice yoga at sunrise, or enjoy a refreshing swim in the warm turquoise waters. Spend your days fishing or barbecuing on the beach while watching dolphins and manatees play nearby.brbrOur prime location places you just minutes away from a variety of restaurants, shops, and water sport rentals. Experience the vibrant nightlife and cultural events in nearby Sarasota, or visit the famous St. Armand’s Circle for shopping and dining.brbrMake Cabana Beach Club Unit 9 your home away from home on Longboat Key. Book your unforgettable beach getaway today!br

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Sleeps

$409.63

/ Nightly

Condo

Longboat Key Beachfront - Beautifully Updated with Prime Location

Longboat Key, Florida, United States

Come enjoy this beautiful beachfront condo! brbrCompletely renovated and updated,, this condo is located at the desirable north end of Longboat Key on one of the most beautiful beaches on the West Coast: white sand, shells, no crowds. The complex has only 64 units in four, 2-storey buildings; all units have their own private outside entrance. This unit is on the second floor where the ocean views are spectacular, including gorgeous sunsets. The condo is done in soothing beach colors (light yellow, blue, white and coral). The living area and master have mirrored walls, enhancing the views, and both open onto a large screened lanai. The living area has a queen sleeper sofa, love seat, chair and ottoman. There is a large TV with DVD. The dining has a table that will seat 10 and a buffet/server. There is colorful art throughout. The kitchen opens onto the dining area to give a light, open feeling. There is a small den off the kitchen with a full-size sleeper sofa and a closet with washer and dryer. Completely furbished, the kitchen has service for 12, many serving dishes and extra appliances including a Keurig coffee maker and an electric wok. The master suite has a king bed, dresser and a flat screen TV. Open the sliding doors to listen to the ocean, or close the room-darkening blinds if you want to sleep late. There are both a dressing area and a bathroom with shower off the master suite as well as a walk-in closet. New cabinets and granite counters can be found in both bathrooms. The second bedroom has twin beds, a single sleeper chair, a flat screen TV and its own complete bath. The beachfront pool can be accessed from the beach or the parking area and there are 2 tennis courts across the street for the exclusive use by Cedars West residents and guests. A barbeque grill is available on site.brbr(Please note that the Cedars West Condominium Association does not permit rentals for fewer than TWO WEEKS).br brLongboat Key is close to both Bradenton and Sarasota, one of the cultural centers of the West Coast. Activities abound for everyone. Nearby are fine and casual dining, golf, parasailing, diving, kayaking, theater, movies, opera, night life. Kids can have fun at Jungle Gardens, Mote Marine or playing miniature golf. Go deep sea fishing and cook your catch in your own kitchen. Plan a morning shopping in the upscale shops on St Armand's Circle and have lunch at the Columbia or another of St Armand's fine restaurants. Rent a bike or take the free trolley up to Bradenton Beach to have a beachfront meal. This is the place for you if you are looking for a relaxing and fun stay at the beach. brbrKeywords: Beachfront, Beach, Longboat Key, Cedars West, Gulf Coast, quiet, calm, waterfront, tennis, Pool

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$190.62

/ Nightly

Condo

Stunning Canal Condo - Walk to Beach - Sleeps 4

Longboat Key, Florida, United States

***HOME WITH CANAL VIEW/WALK TO THE BEACH***brbrPleasant 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 décor offering two bedrooms on the second floor with a king sized bed and 42” TV in the master bedroom, and two twin beds in the second bedroom. The linen closet is stocked with an inflatable mattress and beach towels. The kitchen is equipped with a microwave, stove, oven, toaster, blender, coffee-machine and a brand new dishwasher, new sink and faucet.brbrThe living area and master bedroom feature sliding glass doors to the canal. Wake up and step out into the balcony overseeing the canal and breath in the tropical breeze while listening to the palms sway. Have morning coffee or tea in our patio table and keep an eye open for the marine life that tends to drift down the canal. The living room has a smart 65” TV and we offer 600 MBPS fast speed free internet perfect for working remotely. brbrTake a short walk to the white sandy beaches with crystalline waters in the Gulf of Mexico and catch the most breathtaking and very private sunsets. We include in our rental beach gear such as umbrella with chairs, small cooler, boogie board and paddles. You are welcome to use our beach wagon.

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Sleeps

$317.56

/ Nightly

Cottage

Historic Longbeach Village Cottage - Private Home

Longboat Key, Florida, United States

brAll repairs since hurricanes are now complete.brbr 'Sunny Side Up' is a restored beach cottage built in the 1950's located on the north end of Longboat Key in historic Longbeach Village. The feel of Old Florida with all the modern conveniences. brbrWall Mounted Flat Screen HDTVbrbrWifi internet can take you from the Beach to the 'Home Away From Home Office' in a breeze. Secluded in a private lush tropical garden with outdoor deck patio, you can also 'Get Away from It All'.brbr'Sunny Side Up' is a short stroll from waterside dining at Mar Vista Restaurant and Pub and Shore where you can watch the dolphins feed. Just minutes away is St. Armands Circle for loads of shopping and dining fun. Have I mentioned gorgeous Whitney Beach isbrjust a short walk away It is not uncommon to view dolphin and manatee if you watch carefully.brbrBuilt when they knew how to build featuring Gorgeous Southern Longleaf Pine Floors, Tongue and Groove paneling throughout, and large windowsbrto watch for peacocks.brbr3 Bedrooms with 1 King and 2 Twin over Full Bunk Bedsbrbr2 full bathrooms indoors - one updated with large step in shower, other has tub/showerbrbrFlat screen HDTVbrbrDVD PlayerbrbrSecured WIFI InternetbrbrPrivate Outdoor ShowerbrbrNewly Remodeled and Fully furnished kitchen with breakfast bar includes stainless appliances, cookware and dishware - opens to den featuring french doors.brbrLarge outdoor deck area with table for six and lounge seating area by gas grill.brbrAttached garage/screened in outdoor dining area.brbrFull Sized Washer / Dryer.brbrWe also provide Bikes, Beach Towels, Chairs and Umbrellas.brbrOutdoor activities abound with boating, fishing, kayaking, parasailing, jet ski, and bicycle rentals all nearby. Bike trails and sidewalks can take you the length of the island.brbrJust North over the bridge is Anna Maria Island with all itsbrrestaurants and beach shops.brHeading South you are a short bike ride or 2 mile walk from Joan M. Durante Park, Recipient of '1998 Outstanding Ecosystem Restoration Award' withbrwinding plank trails overlooking Sarasota Bay and a great kids playground. Mote Marine Laboratory invites you to observe Florida sea life including dolphins, manatees, and seahorses.brSarasota is just over the bridge from St. Armands Circle with theaters, opera, symphony, museums and art galleries, and, if you time it right, the Pittsburg Pirates train in nearby Bradenton.brHave I mentioned gorgeous Whitney Beach is just a short walk away brHope you can come and Enjoy!

3

Bed

2

Bath

6

Sleeps

$365.54

/ Nightly

Condo

Resort Style Gulf Front Living

Longboat Key, Florida, United States

Arbomar offers a perfect blend of classic Florida charm and modern coastal comfort. Set directly on the Gulf of Mexico, the property delivers a peaceful, boutique atmosphere with beautifully maintained grounds, lush tropical landscaping, and a private stretch of sugar‑white sand just steps from the building.brbrOne of the best views on the islandbrbr✨ What Guests Love About Unit 604br6th floor offers amazing views.brbrThe balcony sunsets are a nightly highlightbrbrThe unit is clean, modern, and thoughtfully furnishedbrbrEasy access to the beach, pool, and all community amenitiesbrbr✨ Interior HighlightsbrTwo Bedrooms and Two Bathrooms. The primary bedroom offers a King bed and the second bedroom offers a Queen bed.brbrSpacious open‑concept living area with abundant natural lightbrbrPrivate balcony with sweeping views of the Gulf and the Arbomar groundsbrbrUpdated kitchen with modern appliances, ample counter space, and a clean coastal designbrbrComfortable bedroom accommodations with generous storagebrbrWell‑appointed bathroom with contemporary finishesbrbrTasteful décor that creates a relaxing, beach‑inspired atmospherebrbr✨ Comfort & ConveniencebrHigh‑speed Wi‑FibrbrCentral A/CbrbrOn‑site laundry facilities on same floor no additional charge brbrSecure building entrybrbrElevator access to the 6th floorbrbrbrGuests enjoy a relaxed, resort‑style experience with amenities designed for both leisure and convenience. The heated Gulf‑front pool provides sweeping water views and plenty of space to unwind. A spacious sundeck, shuffleboard courts, and a community grilling area make it easy to enjoy outdoor living. Inside, Arbomar offers a fitness room, a welcoming clubhouse, and secure building access with on‑site management that keeps the property pristine.brbrLocated mid‑island, Arbomar sits minutes from Publix, CVS, restaurants, St. Armands Circle, and the island’s scenic walking and biking paths. It’s the ideal home base for anyone seeking a quiet beachfront escape with easy access to everything Longboat Key has to offer.brbrOne Month Minimum StaybrHOA approval and fee required

Bed

Bath

Sleeps

$544.54

/ Nightly

Private Vacation Home

Beautiful Beach Island Home

Longboat Key, Florida, United States

This stunning property is a large two-story home on Longboat Key with private deeded beach access, pool, hot tub, dock, and canal. The beach path houses a box with chairs and beach toys reserved for this property, as well as there is a beach wagon provided if additional beach toys and supplies are needed on the beach. The heated pool is private with chaise lounges, chairs, dining area, grill, pool toys, and a hot tub. brAn expansive paver patio stretches the length of the back of the house along the canal with areas for sitting and eating. The dock can secure a boat and nearby marinas rent boats for visitors. There is also a garage for guests. brThe house has four porches, one overlooking the lush back area and canal; the front porch overlooking the front garden; the side porch faces the pool and houses a dining table and chairs, and the upstairs porch extends from the master bedroom overlooking the pool from the second story. This upstairs porch has a hammock, and seating area. .brThe downstairs features a spacious 22-foot ceiling living room with two sets of French doors that open to the back porch. A fireplace and baby grand piano mark the front entryway downstairs. There is a separate office, TV room, and full bathroom.brThe kitchen has every desirable amenity and two French doors that open to the side porch with table and chairs and grill. There are two tables and seating arrangments at either end of the large kitchen, which includes an island and bar for seating. The dining area seats 12 people, plus the 3 stool bar. brUpstairs there are three bedrooms and two baths. Two bedrooms share a full bath in a separate wing. One bedroom has a queen size bed with a window seat and the other bedroom has a twin bed with French doors overlooking the back tree-lined canal. brThe master bedroom has a king size bed, French doors that open to a private porch, and another French door that overlooks the back canal. There is an attached full bath with both a tub and separate shower.brThe house is fully equipped with all supplies needed, including towels for both the home and beach; kitchen and picnic supplies, propane grill, board games, and household supplies.br

3

Bed

3

Bath

5

Sleeps

$400.82

/ Nightly

Condo

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Longboat Key, Florida, United States

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifacts, 40 year old flooring, one SIZE fits all, etc.). We call it upscale coastal. The properties are more of a resort, 5 star hotel feel. We own an elegant upscale home next door, a penthouse unit, a direct walk out unit, along with 2 units with the option to connect into one suite. brbrYou’ll find everything you need on-site from free WIFI to dishes, linens, towels and even a few extras you may need for your stay like puzzles and soap. There is a pool and a covered area with grills and picnic tables overlooking the beach. Hope to see you soon at one of my beautiful vacation homes. All you need is your bathing suit and a toothbrush. The beach is just steps away. brbrThis resort is not a place of public accommodation as defined by the ADA and, therefore, does not meet the accessibility requirements of the ADA. That said, there are some accessible features at the facility. Please ask me specific questions to determine if this property would a good fit for your needs.brbrPlease view my other beautiful vacation homes and make plans now to visit Longboat Key to see why we love it!!!br247170 - Zilli Villa is a two bedroom, two bath house located right on the beachbr4649102 - Zilli Ocean Front 101 is a direct walk outbr7900243 - Zilli Ocean Front 201 and 9070766 - Zilli Ocean Front 202 are individual condos that can be made into a suite for larger groups with a connecting door.br

Bed

Bath

Sleeps

$222.26

/ Nightly

Private Vacation Home

Tree-lined home w/ amazing decor & screened porch - near beach/dining

Longboat Key, Florida, United States

TreetopsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the stunning beauty of Florida's Gulf Coast at this wonderfully positioned home among the palms of Longboat Key. The interior of this home is a thoughtful, light-filled showcase of international decor and furnishings, which the owner - a seasoned world traveler - has collected in her travels across Asia. You'll enjoy a screened-in porch, a sleek, air-conditioned living space, and an enviable location just one block from a secluded beach.brbrWhat's nearby:brWhether you're a beach-goer, an angler, or a snowbird flying south for the winter, you'll find plenty to keep you occupied on Longboat Key. You'll be only one block from a tranquil beach on the Gulf of Mexico. Schedule a morning match at the Longboat Key Public Tennis Center, which maintains 10 clay courts that are available for reservation. You could also rent a boat at Cannons Marina and spend an afternoon birding near Longboat Pass (half a mile north), still making it home in time to catch a spectacular sunset over the Gulf.brbrThings to know:brFree WiFibrFull kitchenbrThis property has a 30-night stay requirement. However, select properties have the flexibility for shorter stays.brbrThe property is managed by Vacasa Florida LLC.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 4 vehicles.brbrDock details: Longboat Key Marina - full-service 291-slip, deep-water marina. brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

3

Bed

2

Bath

7

Sleeps

$228.09

/ Nightly

Condo

Grand Bay 626 by FVC

Longboat Key, Florida, United States

Luxury Waterfront Retreat at Grand Bay – Unit 626, Longboat Key brbrExperience the ultimate in coastal elegance at this stunning waterfront condominium at Grand Bay on Longboat Key. Professionally managed by Florida Vacation Connection, this beautifully appointed two-bedroom, two-bathroom residence offers breathtaking bay and golf course views, resort-style amenities, and a prime location near St. Armands Circle and downtown Sarasota. brbrStep into a bright and spacious open-concept living area, where floor-to-ceiling windows showcase the sparkling waters of Sarasota Bay. The expansive terrace provides the perfect spot for morning coffee or evening cocktails as you take in the serene surroundings. brbrThe fully equipped gourmet kitchen boasts granite countertops, modern appliances, and ample space for preparing meals. The elegant primary suite features a king-size bed, terrace access, a spa-like en-suite bathroom, and walk-in closets. The guest bedroom is thoughtfully designed with comfort in mind, making it a welcoming retreat for visitors. brbrAs part of the exclusive Grand Bay community, guests will enjoy access to a wealth of resort-style amenities, including: br- A heated waterfront pool and spa br- A state-of-the-art fitness center br- Tennis courts for friendly matches br- A private beach club for residents and guests br- 24-hour gated security for peace of mind brbrLocated just minutes from white sandy beaches, world-class dining, and upscale shopping, this luxury retreat is the perfect escape for those seeking relaxation, adventure, and everything in between. brbrBook your unforgettable Longboat Key getaway today!brbrTown of LBK RRR-01259.2025

2

Bed

2

Bath

4

Sleeps

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