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Longboat Key Vacation Rentals

We Have 627 Vacation Rental Offers Available In Longboat Key. Average Price Per Night Is $302.74. Find Your Vacation Home Today.

Showing 20 Of 627 Vacation Rentals
  • Property-1 Image 1
    Breathtaking Gulf and Beach Front Condo with Balcony and Pool
    Condo $350 / Nightly
    • (8) Exceptional
    • 3 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    From the moment you walk in the door of this 2 1/2 bedroom, 2 bath beach front condo you will know you made the right choice for your beach escape. Remodeled from the studs in 2019, this unit was transformed into this high quality, coastal retreat and is unlike any other condo on the Key. So much attention to detail in this beach condo shows up in every room. brViews: Breathtaking views of the Sarasota Gulf waters with its ever changing spectrum of blues. Located on the 4th floor of Tiffany Plaza Condominiums in the center of 7 mile Longboat Key, known for it's white sand and clear blue water. brKitchen: So perfect that you might actually want to cook while you’re on vacation! Most every kitchen appliance, tool and cookware is stocked. brLiving: Large living room with comfy new furniture and plenty of space to pull up more chairs when you you need to. brDining: The dining table has 4 larger chairs. But can seat 6-8 with leaf added. The four barstools add additional seating at the island. brMaster: Wake to beautiful views of the water from 2 walls of the Master bedroom. Sliding doors open to the balcony. brBaths: Completely and thoughtfully updated baths with high quality finish out.brGuest Bedroom: Quiet queen bedroom with dresser, club chair and TV. brFlex Room: Flexible room with desk, sleeper sofa and flat screen TV. brBalcony: Looking for a good spot to watch the sunsets with a cocktail or have your coffee every morning? This is sure to be your favorite with its L-shaped sofa and Bistro table overlooking the blue green waters of the Gulf. brbrPool: Heated complex pool on the South side of Tiffany Plaza. brbrBeach storage: Tiffany Plaza has a beach side hut for short term storage of your beach chairs and umbrellas. brbrThe Beach: Longboat Key has 7 miles on each side of the island to walk, explore, fish and relax with arguably the most beautiful waters and sunsets in the world. brbrLocation: Longboat Key is conveniently located between Sarasota/St Armands Circle and Anna Marie Island and is known for its miles of white sand beaches, blue green Gulf waters, and breathtaking sunsets. brbrProvided with the condo: brBath and beach towels, bed linens, hairdryers, one full size shampoo, conditioner, body wash and hand soap provided per stay in each bathroom. Starter pods for the Kurig coffee maker, dishwasher and washing machine. Starter dish soap, paper towels and toilet paper. brMost every kitchen appliance, tool, cookware and dishware is stocked, so please ask us if you would like to know if we have a specific item. brbrOptional Services: br- Order groceries, beer and wine to be delivered upon your arrival from the Publix grocery store on the island so your vacation can begin immediately upon your arrival! br- Add on weekly or mid month housekeeping for $150-$200/cleaning. brbrTreat yourselves to a stay at this fresh, new beach condo and you will want to make it your home away from hone year after year. brbrbrPLEASE NOTE: br- Renters will need to sign a rental agreement with the property owners and provide info to the Tiffany Plaza HOA. br- Search 3 Palms by the Beach online for more info. Read More

  • Property-2 Image 1
    Inn on the Beach 6-203
    Condo $306 / Nightly
    • (2) Excellent
    • 2 Baths
    Longboat Key, Florida, United States

    Florida Vacation Connection is proud to offer this tastefully decorated and spacious 642 square foot studio overlooking Island Lagoon. br From the moment you walk through the front door, you will notice the attention to detail reflective of the Gulf, sand, our protected Sea Turtles and relaxation. Your eyes will slowly move out to the expansive views of the lagoon. br Sit on your oversized open air balcony and take in the views of the lagoon to watch the boats, kayaks, SUP's, and hydrofoil ...br ...surfboards. Have your beverage of choice with breakfast here watching the incredible sunrises reflected in the lagoon to energize your day. br Throughout your day, you will experience the efficiency of the layout of this junior suite with the microwave doubling as your convection oven, affording you the opportunity to prepare for any activity, whether swim suite, office suit, or gala attire. Spacious closets with extra storage invites you to stay longer. br Rinse the day away with the waterfall shower head or soak in the tub. Then repose to the Ergonomic Sleep Number bed with independent settings where you travel through your sleep journey, drifting off to swim with the dolphins and turtles.br Every attention to the details has been made to ensure you awaken to the calming emerald tones of the sea and the creatures she protects. Discover the starfish, sand dollar, and sailing clipper all watched over by the sands of time slowly dropping through the hourglass. br Come and experience your own aquatic escape in this junior suite. Even stayover guests can enjoy the pullout sofa with its Gel Memory Foam mattress top. Something for everyone!br Added conveniences include a brand new front-loading washer and dryer, iron, ironing board, hair dryer, new refrigerator-freezer, and cork floors for sound absorbtion. And don't forget that 10' x 20' balcony! br With the beach only a short walk away, you will have access to the pool and hot tub area equipped with chaise lounges and umbrellas which is a great place to relax, so swimming and sunning enjoyment is yours to be had.br We know you will enjoy the luxurious club suite, where you will discover the special ambiance of Longboat Key and its beautiful beaches.br Our guests have access to the beautiful private beach, pool and hot tub area only. Resort amenities (golf, dining, tennis, room & maid service or fitness) are private and not included. No money is exchanged on the property.br COVID-19 SANITATION PRACTICES & PROCEDURES: For those who are ready to resume planning their much-needed beach vacation, our team is available to assist you in scheduling your vacation! Florida Vacation Connection has strict cleaning and sanitization procedures to comply with CDC recommended guidelines. Your health and safety is our priority!br Amenities Include:br - VIEW:: Lagoonbr - MAXIMUM OCCUPANTS:: 4br - # OF BEDROOMS:: 0 - Spacious Studiobr - # OF BATHROOMS:: 1br - MASTER BEDROOM: King bedbr - Parking: Openbr - DISTANCE TO BEACH:: Walkbr - LANAI:: Yesbr - WiFi:: Yesbr - # OF TELEVISIONS:: 1br - WASHER AND DRYER:: Yesbr - SWIMMING POOL:: Communitybr - HOT TUB:: Communitybr - DEPARTURE CLEAN FEE:: $125.00br - TENNIS:: N/Abr - FITNESS CENTER:: N/Abr ... Read More

  • Property-3 Image 1
    Single level, 2 bed/2 bath condo just steps to the beach!
    Condo $159 / Nightly
    • (4) Exceptional
    • 2 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    If you love the beach, this is your place! Literally a one to two minute walk to the beach, this single level condo with it's own backyard is extremely well appointed with multiple upgrades including brand new king size bed, new sectional couch with chase, new art work, new linens...the list goes on. The location on the island couldn't be better as you can walk to the Publix grocery store, drug store, liquor store, nail salon, tennis courts, library plus more! There are many restaurants and shops within a 5-10 minute drive of the condo. Downtown Sarasota is only 15 minutes away. brThere are only 10 units in this charming community. Book your getaway today! Read More

  • Property-4 Image 1
    Waterfront - Canal - Dock - walk to private beach – Home
    Private Vacation Home $225 / Nightly
    • (1) Very Good
    • 3 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Welcome to Florida’s Tropical Paradise. Once you drop your suitcases, you’re a 3-minute walk to a private beach entrance, access to the highest-rated beaches in the US. Relax on the soft sand or in the crystal-clear water, then watch the sunset from your own gazebo (complete with a freshwater shower).brbrWhen you return home, you’ll enter to shiny terrazzo floors and a fully equipped kitchen with stainless appliances. The kitchen, dining area, and living room make an abundant entertaining space, with enough room to spread out and socialize. Every bedroom is upgraded with a smart flatscreen TV and high-speed Wi-Fi throughout.brbrThe large Florida Room is a great place to unwind, overlooking the private canal dock. Feel free to bring your own boat or rent a boat/jet-ski at nearby Marinas. Longboat Key is full of adventures, through countless sandbars and small islands to voyage, minutes away from Sarasota and Bradenton, with many waterside restaurants.brbrBayfront Park is a 5-minute walk; amenities for all ages; playground, a basketball court, shuffleboard courts, tennis and pickle ball courts, picnic benches and a dog park, with beautiful views of Sarasota Bay. St. Armand’s Circle, with its upscale dining/shopping and Bradenton Beach, a quintessential beach town, are just 15 minutes away.brbrbrbr******** Minimum monthly rental ******** Read More

  • Property-5 Image 1
    Clear Skies: Beautiful 3 BR / 2.5 BA ranch home with pool.
    Private Vacation Home $239 / Nightly
    • (2) Very Good
    • 3 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Beautiful and spacious 3 bedroom, 2.5 bath ranch home, nestled in the quaint Buttonwood Harbour neighborhood of Longboat Key. It is only a 5-min. walk to the deeded white sand beach, with roaming sea birds and beautiful sunset.  This home situated in a picturesque tropical garden with mature stunning oak trees, and is very close to dining and shopping. This beautifully appointed home has been nicely updated and features a private heated pool, with an outdoor shower for your enjoyment in the winter months. The Master suite is large and has a King sized bed and overlooks the pool. The ensuite has dual sinks and a walk in shower. The first guest bedroom features a King sized bed while the second guest bedroom has two full beds. The two guest bedrooms share a bath which has a shower/ tub combo. A great home for relaxation, with the open floor plan, and various seating areas, and the tranquil surroundings. The home office is located adjacent to the Master suite, overlooking the Florida room, and the house is fully equipped with WiFi and cable if you need to work from home. This lovely home is your home away home in winter. Conveniently located near the Publix Shopping Center and just a short drive from Sarasota­-Bradenton International Airport. Near St. Armand’s Circle and Downtown Sarasota where you will find unlimited shopping and dining options. brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties. No pets. Guests do not have access to the garage except for trash and recycling purposes. brbrPool heating is optional, for an additional non-refundable fee of $25 per day + taxes to be paid directly to the management company after the reservation is confirmed. brbrThere is an outdoor shower as well. brbrPlease note, Gulf Coast Property Management reviews all reservations before a final booking confirmation is sent to guests. Seasonal (January – April) reservations are accepted in chronological monthly succession. Reservations are not guaranteed until the final confirmation email from Gulf Coast Property Management has been received. Read More

  • Property-6 Image 1
    BOOK NOW - BEAUTIFUL HOME, BEACH ACCESS!!
    Private Vacation Home $393 / Nightly
    • 3 Bed
    • 3 Baths
    Longboat Key, Florida, United States

    ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighbourhood. Take a leisurely 5 minute stroll to the 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. Read More

  • Property-7 Image 1
    COZY ISLAND RETREAT AS LOW AS 59.00 PER NIGHT
    Private Vacation Home $71 / Nightly
    • (19) Excellent
    • 4 Bed
    • 3 Baths
    Longboat Key, Fl, United States

    HOUSE HOLDS 8 GUESTS KITCHEN HAS UPDATED APPLIANCES FULLY EQUIPPED WITH UTENSILS DINING ROOM 4 BEDROOMS 3 BATHROOMS 2 WALK IN SHOWERS 1 WITH JETTED TUB 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 brbrLIGHTED BACK YARD FOR NIGHTLY ENJOYMENT brbrHARRY"S FINE DINING, GROCERY STORE AND DELI ON SAME BLOCK HAS BEEN THERE FOR 30 YEARS brbrBEACH IS A NEIGHBORHOOD BEACH IS QUIET TO ENJOY AND RELAX ABOUT A HALF BLOCK AWAY SHORT WALK AMAZING GULF OF MEXICO VIEWS ON THE BEACH brbrSTREET IS VERY PEACEFUL AND QUITE brbrFISHING FULLY PACKED FAMILY ENTERTAINMENT Read More

  • Property-8 Image 1
    Sea Grape Inn #3 - BEACHFRONT Property
    Apartment $368 / Nightly
    • (4) Exceptional
    • 2 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    *Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*brBEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brThis 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 master bedroom suite has been upgraded and includes a view of the water and flat screen TV. The master bath has 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. With the exception of the kitchen and baths there is carpet throughout.br*Required $135 Departure Cleaning Fee. brFor more property details and condo virtual tours, visit our Website:brVIRTUAL TOURbrTheSeaGrapeInn.combrView Property Amenities brCANCELLATION 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, No Refund Or Booking Credit will be provided.brbrFree Wifi Read More

  • Property-9 Image 1
    Unit #218 Sand Cay Beach Resort Gulf Front
    Condo $400 / Nightly
    • 2 Bed
    • 2 Baths
    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. Read More

  • Property-10 Image 1
    Beachplace 1-502: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 4
    Condo $197 / Nightly
    • 2 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Welcome to Beachplace 1-502, a spacious 2-bedroom unit in the desirable community of Beachplace. Relax on your private patio and soak in the warm Florida breezes - the Gulf of Mexico views from this unit will keep you coming back year-after-year. This two-bedroom, two-bathroom condominium is spacious and nicely decorated, and includes everything you need for a relaxing getaway. Additional features include wireless Internet access, covered parking and more. The Beachplace Condominium complex includes a large community pool and hot tub area, private beach access, and additional Internet access at the Clubhouse. Leave your worries at home and start relaxing in the Florida lifestyle!brbrbrbrAccommodations: Two-Bedroom, Two-BathroombrbrbrbrAmenities: Private Deck, Upscale Furnishings, Gated Community, Elevator, Full-size Kitchen, Community Pool, Washer/Dryer, Wireless Internet, Great Location, Parking under Building, Community Grill, Fitness Facility, Locker Rooms with SaunabrbrbrbrLocation: 1145 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $150 Fee + Application; $25 Cancellation Penalty Read More

  • Property-11 Image 1
    Beautiful home boasting private pool & private beach access
    Private Vacation Home $329 / Nightly
    • (2) Exceptional
    • 3 Bed
    • 3 Baths
    Longboat Key, Florida, United States

    Gulfside Stroll on Longboat KeybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis beautiful and spacious family-friendly home is perfect for your next beach getaway. Only 250 feet from your door, you will find the private beach access point leading you to the azure waters of the Gulf of Mexico. After a day at the beach, the private pool awaits, featuring a spa and plenty of space to lounge and relax under the lanai! The kitchen is equipped with all the essentials perfect for preparing a small snack or a chef's meal. This property boasts plenty of space, has full tile and laminate flooring, and offers the experience of living the true Florida lifestyle. Extra perks include beach chairs, umbrellas, a cooler, and toys.brbrJust a short drive away, you will find the exclusive town of Longboat Key offering many restaurants, including Mar Vista, Euphemia Hay's and Mason Blanche, as well as shopping and entertainment options. Anna Maria and Sarasota are just a short drive further, offering even more! With private beach access and quick access to the area's prime offerings, there is no shortage of fun and relaxation.brbrTHINGS TO KNOWbrDogs are strictly prohibited due to the owner's severe pet allergies.brbrParking notes: There is parking for 3 on the front driveway and 3 spaces on the rear driveway entering off Gulfside Road. No parking on the lawn.br3 day notification is required in order to heat the pool and pool spa. A fee of USD40 per day must be paid prior to check-in. Guests can contact Vacasa after booking to purchase pool and pool spa heat for your stay.brbrbrDamage 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.brbrbrCity/town permit number: 11898brState/province permit number: DWE5106140 Read More

  • Property-12 Image 1
    Perfect Place on LBK!
    Condo $263 / Nightly
    • (5) Exceptional
    • 2 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Family (and dog) friendly townhouse condominium with wonderful amenities all around! Tennis, Largest Pool on LBK, free bike rental, 24 hour gym access, and use of Kayaks!brbrCedars East Tennis ResortbrbrJust updated for your vacation comfort! brbr-2 BR, 2.5 Bath – 1440 square feetbr-Partial Bay views out of Kitchen and 2nd bedroom windowsbr-King sized bed in master with huge closet, two sinks and two vanities, new faucets and new hardware, large bathroom with new toilet and newly painted, cable tv with abundance of channels, and a new ceiling fan. br-2nd bedroom has partial view of the bay with two twin beds, huge walk in closet, cable tv with many channel choices and a new ceiling fanbr-2nd bathroom newly renovated!br-2 brand new air conditioning units with ‘nest’ controls for extremely accurate coolingbr-All new linens/bedding throughout the condobr-High speed internet throughout the condobr-Convenient washroom on bedroom level with washing machine and dryerbr-Kitchen has partial bay view with new refrigerator, updated dishwasher, oven/stove and microwave. All new cutlery, dishes and glassware. br-Convenient 6 person seating in dining area plus 3 new stools for seating at the kitchen counterbr-Living room has 65” HDTV with an abundance of channels. New console table and new coffee table. Sleeper sofa can sleep two people. br-Beautiful, open Lanai with new table and chairs as well as two new Adirondack chairs, new ceiling fanbr-Huge garage has plenty of storage for car, kayak, paddle board, bikes etc.br-beach items provided – new beach wagon, chairs, coolers, umbrellas, towelsbr-Updated keypad for entry, convenient bc you do not need a keybr-Bay access just steps from the front doorbrbrbrComplex Amenitiesbrbr-Jr. Olympic size swimming pool (largest on Longboat Key), lounges and umbrellas providedbr-10 Beautifully maintained Har-Tru tennis courtsbr-24 hour fitness center, shower and locker room in clubhousebr-bay access at rear of 800’s sectionbr-fishing pierbr-On-site restaurant in clubhousebr-beautiful mangrove walkways throughout cedars complexbr-free bike rentals at Cedars clubhousebr-short walk to the private Gulf beachbr-5 min drive to Coquina public beach with beach chair/umbrella rentals and all amenities availablebr-Harrys convenience store within walking distance and several shops and restaurants close bybr-10 min drive to St. Armands shopping/restaurants on Lido Keybr-10-15 min drive to Anna Maria Islandbr-20 min drive from Sarasota airportbrbrLocated on picturesque Longboat Key, directly on beautiful Sarasota Bay and near fantastic Gulf of Mexico beaches, is 821 Evergreen Way at Cedars East Tennis Resort. The condo is just steps from Sarasota bay and is a short walk from the private Gulf beaches. Cedars offers the best location directly in the middle of Longboat Key, where you will have access to beautiful west coast Florida waters just outside your door, and you will have access to amazing dining, shopping and lots of other activities just to the north and south. The Cedars complex stretches from Sarasota bay, to Gulf of Mexico drive, which is Longboats only main road. The resort is beautifully maintained. It is always clean and trimmed and is a pleasure to come home to after a day of boating, tennis, kayaking, fishing, golf, biking or just spending time at the beach or pool. The areas incredible white sand beaches are close by as the private beach is a short walk from our condo, and the beautiful public beach is only a 5 minute drive north. The public beach offers chair/umbrella rentals, and has every beach amenity. For the private beach, we provide chairs, umbrellas, coolers and towels. We also provide a brand new beach wagon to make it easier for you to transport all of your beach gear. The beautiful mangrove walkways in the Cedars complex provide an enjoyable way to navigate the property. The pool is a short, 5 minute walk through the mangroves from our condo. The condo location is perfect as everything that you could possibly need or want for a great vacation is either here, or close by, while also being private. We enjoy biking and often take advantage of the free bike rentals at Cedars. We ride to the public beach just to the north. We also ride several miles to the south, to shop/dine at St. Armand’s circle. There are large sidewalks on Longboat which provides safe and enjoyable walking/biking paths to explore the area. Dining options in the area are numerous, excellent and nearby. There are several great restaurants within walking distance of Cedars complex. There are also many delectable dining options to the north on Anna Maria Island, and to the south in St. Armand’s circle. If you enjoy eating in, there is a Publix supermarket just a 5 minute drive south from Cedars on Gulf of Mexico Drive. With regard to cultural activities, the downtown Sarasota area has great museums, shows, restaurants and other “city” life just a short 10-15 minute drive south on Gulf of Mexico Drive as well. brThe Longboat Key area and Cedars condo complex provide you with everything you could possibly want for a beach vacation, from water sports rentals to fishing, from georgeous white sand beaches to the largest pool in the area, from shopping to dining. #821 Cedars East Tennis Resort is right in the middle of all and the perfect family warm weather retreat. Read More

  • Property-13 Image 1
    LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH
    Private Vacation Home $553 / Nightly
    • (43)
    • 4 Bed
    • 4 Baths
    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. The 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!brbrKeywords: Luxury Beachfront House Read More

  • Property-14 Image 1
    Beachfront Condo with a Beautiful, Renovated Kitchen, Shared Pool, & Tennis!
    Condo $184 / Nightly
    • (1)
    • 1 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Whitney Beach View 332brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLife is good at Whitney Beach! From the moment you enter the private courtyard patio, you'll realize you've finally found the island retreat you've been looking for. This inviting, ground-floor condo has been professionally updated with tray ceilings and custom lighting, with views of the Gulf of Mexico and gorgeous sunsets to dazzle you across the lushly landscaped grounds. The comfortable living space opens directly to a covered beachside patio, where you're certain to enjoy everything this desirable gulf-front setting has to offer, including fabulous views and gentle island breezes.brbrWhat's nearby:brIn addition to the tranquil beach atmosphere, you'll have easy access to all amenities offered in this special gulf-to-bay community, including a swimming pool directly on the beach, beachfront tennis courts, a barbecue and Tiki cabana, boat docks, and a fishing pier. When you're ready to explore Longboat Key, Anna Maria, or Sarasota cultural venues, you're only a short drive or trolley ride away. Beer Can Island - a low-key sand bar with a rustic, powdery beach for picnics and parties - is less than one mile away.brbrThings to know:brFree WiFibrThere is a 30-day minimum stay per town/HOA ordinance, and guests must submit the HOA application and pay a $100 application fee to book this condobrbrThis property is managed by Vacasa Florida, LLC.brbrParking notes: There is one space in front of the condo. Visitor parking is available in the parking lot.brbrDock details: brbrbrbrDamage 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.brbrbrCity/town permit number: 12122brState/province permit number: CND5105555 Read More

  • Property-15 Image 1
    Paradise Awaits: Exquisite 3 BR Private Beach Condo
    Condo $279 / Nightly
    • 3 Bed
    • 3 Baths
    Longboat Key, Florida, United States

    Welcome to Paradise Awaits! This stunning 3-bedroom, 3-bathroom second floor condo is located in the highly sought-after community of Villa Di Lancia, in Longboat Key, offers private beach access! brbrThis condo is only a few steps away from the white powdery sands and crystal blue waters of The Gulf of Mexico. brbrVilla Di Lancia, has one of the largest pools in Longboat Key. There is an eleven-person hot tub, state of the art fitness center, sauna, Har-tru tennis courts that can also be used as a Pickleball Court. This community is gated with a guard 24 hours. brbrVilla Di Lancia is located just South of Bay Isles for boutique shopping and exquisite dining while also close to world famous St. Armand’s circle for nightlife. This is Longboat Key living at its’ finest.brbrThis condo has a private entrance, and private elevator taking straight to the condo. Open entry you will find a light and bright atmosphere. The living room has a large sectional, an adjoining day chair, and a TV. From the living room you have ocean views. There is a set of sliding glass doors that will lead you to the oversized balcony that 360 views of the Gulf of Mexico and community pool. You will never want to leave! The kitchen is spacious, with a large island and plenty of countertop space. There is also a breakfast table and an area for you to set up your remote office. brbrThe primary bedroom, has a set of doors leading to the balcony, ocean views through the large windows, a king-size bed. Attached is the primary bathroom that has marble flooring, two vanities, a soaking tub, and a large walk-in shower with dual shower heads. The second bedroom has two twin-size bed, some chairs, and plenty of space for your personal belongings. The second bathroom, has a large vanity with a walk-in shower. The third bedroom has a space for you to set up a remote office, a pull-out sofa, a TV and additional seating. The third bathroom, has a tiled vanity and a walk-in shower. brbrCome, and see why people never want to leave Longboat Key. brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties. No Pets. brbrPlease note, Gulf Coast Property Management reviews all reservations before a final booking confirmation is sent to guests. Seasonal (January – April) reservations are accepted in chronological monthly succession. Reservations are not guaranteed until the final confirmation email from Gulf Coast Property Management has been received. Read More

  • Property-16 Image 1
    BEAUTIFUL WHITE SAND BEACHES ON LONGBOAT KEY FLORIDA
    Private Vacation Home $260 / Nightly
    • (5) Wonderful
    • 3 Bed
    • 3 Baths
    LONGBOAT KEY, Florida, United States

    Come and enjoy Lovely Peaceful Longboat Key & stay in this Beautiful completely updated Home. Imagine just a few steps from White-Sand Beaches. This Home has three levels, as you enter through either the Garages (one on each side) or the front door there's three steps downstairs, where you will find an extra bedroom with a Bunk bed (bottom Full size, top Regular) separated by a Game Room featuring a Pool Table, Pingpong Table and Air Hockey. As you exit you can take a dip in the outside Heated Pool or Spa. You can relax on the adjoining deck to take in some Sun while having your favorite beverage or lunch on the five piece dinette set on the deck. You have access the main floor by the back stairs (to the Lani) or front stairs to Main room, again, a place where you can relax with your favorite beverage on the Lani in a private space, or prepare whatever you desire is an entrance to the Kitchen featuring all the appliances will need. The Laundry Room equipped with a Washer & Dryer and a Pantry for your convince. In the Livingroom there's a 75" Smart TV & complete wireless Internet throughout. Theres a Wet Bar; two bedrooms (Queen Beds) plus two Bathrooms, one with a Shower; the other has a Bathtub plus a Shower. When you want your privacy a-send to the Master Suite, with a complete large Bathroom, Large walkthrough closet. You may also, desire to sit on your own deck for more relaxation. There's also, a 50" Smart TV for your private viewing. This Home offers Space for everyone. brLovely St Armands Circle, are ideal Beach and Bayfront settings for the ultimate Florida Vacation. Stretching between the gorgeous Gulf of Mexico and Serene Sarasota Bay, this area attract many visitors who come to enjoy South West brFlorida , average year- round temperature of 73 degrees. These waters are home to Manatee, Dolphins, and Fish, while Sea Turtles, Pelicans, Osprey, and variety of Shorebirds find sanctuary here. Tennis and Golf enthusiasts will find first-class facilities here, and there are several Parks on the Keys to visitor for a relaxing afternoon. Whether you like to spend your time shelling, biking, shopping, fishing, golfing, or dining, opportunities for these activities are boundless on Longboat Key and St. Armands Circle. The Longboat Key Center for the Arts hosts art classes, workshops, and cultural events here on Longboat Key. Sarasota's many cultural centers are only minutes away over the south bridge, including Van Wezel Performing Arts Center, Asolo Theater, West Coast Black Theater, Ringling Museum, Sarasota Ballet and Opera, and several other live theaters. Come enjoy the Blue Oasis by the Gulf, Award Winning White Sand Beaches (and deeded beach access), St. Armands Circle, and all Longboat Key has to offer! Longboat Key seasonal rental available2020. Minimum stay 30 days or stays long as you like. Fully furnished 3 bedrooms, plus downstairs Bunk Bed, 3 bathrooms, deeded beach access, heated pool and spa, outside pool shower, game room, Stainless steel, granite counters through-out, 2 car garage, beautiful landscaping. Gorgeous property on Longboat KEY, near Publix Supermarket and St Armands. Come and enjoy a piece of Paradise!! Read More

  • Property-17 Image 1
    Georgeous Condo On The Beautiful Longboat Key beach!Cabana Beach unit #9
    Condo $220 / Nightly
    • 1 Bed
    • 1 Baths
    Longboat Key, Florida, United States

    brbrLovely gulf side unit which can accommodate 5 people has 1 bedroom /1 bathroom and is located in a beautiful tropical resort Cabana Beach Club nested just on the white beaches of charming Longboat Key. It is perfect as a romantic getaway or for family vacation. brbrThe unit offers everything you may want and need!!! Fully equipped kitchen has all appliances, new fridge ,all cookware and utensils and plenty of cabinet space.brbrThe condo offers king size bed in the master bedroom and queen pullout sofa as well as a single bed pullout chair that can comfortably accommodate 5 guests total. Linens and towels are provided. The whole unit is nicely remodeled with Florida beach decor, creating the perfect vacation ambiance. brThere is a flat screen smart TV in the living room as well as in the bedroom, High Speed Internet,WIFI and cable .brStarter supply of paper towels, napkins, toilet paper, coffee filters, dishwashing liquid, dishwasher detergent and laundry detergent is provided for all of the guests.brbrGuests have a direct access to the beach and heated pool, which is just in front of the condo. Guests may also use a boat or fishing dock, boat slips can be rented at an additional fee. brbrLongboat Key - on the most beautiful island in the Gulf of Mexico! Great place to relax, enjoy the sun and the beach. Go for a walk on the white sandy beaches, enjoy the sunset, do a yoga at sunrise, take a swim in the warm turquoise water then lounge under the umbrella and watch the dolphins play and manatees, try out fishing and barbecue on the beach. brbrCabana Beach Club's location is convenient to restaurants, shops, bicycle, boat and water sport rentals, Sarasota 's restaurants, evening life, culture events are just couple miles away, as well as the well known St. Armand's Circle, with its vibrating life. Read More

  • Property-18 Image 1
    Just the Essentials, Longboat Key.
    Apartment Select Dates for Price
    • 1 Bed
    • 1 Baths
    Longboat Key, Florida, United States

    Sun, Sand, beach, dock, bikes, kayaks. Sunrises, Great Beaches, Great Fun. Quiet, Peaceful, Tropical Plants, Birds, fish. Dolphin, Manatees. Great Restaurants. All part of your Island experience. Your 1st floor apartment offers open concept living area and kitchenette. Under-counter refrig, microwave, coffee maker, toaster oven and other small appliance. Outdoor gas grill with side burner. DirecTV. An uncrowded white sand beach is maybe 800' from your door. Beach gear, chairs, towels, umbrella, cooler etc. for your use, too. Great restaurants up & down this and adjoining Anna Maria Island. See Lots of Dolphin & Manatees using the Tandem or Single Kayak and PFD Life Jackets included for your use. Bike together in the local neighborhoods and bayfront parks. Public tennis & pickle ball courts available on the island. World class shopping at St. Armand's circle. Read More

  • Property-19 Image 1
    Wow Magnificent home in Longboat Key, Fl
    Private Vacation Home $304 / Nightly
    • (14)
    • 3 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    This is a stunning 3.800 sq foot beach home on a salt water canal. The home is on a private street with a 2 car garage and taller 1 car garage to accomodate a van. Please give me a call for renting time frames other than the time frames listed 941-626-2625 . Long Boat Key beach is approximately 3 blocks away and easily accessed on foot or by car. if you are considering certain dates or weeks please know The online calendar is off and it’s not completely up-to-date please call me to confirm your date availability RENTAL IS ON A MONTHLY BASIS- MUST RENT FROM BEGINING OF MONTH TO THE END- SORRY NO MID MONTH RENTALS ARE ACCEPTEDbr.br Our home has 3 bedrooms. A marvelous master suite holds a king bed with screened in patio to sit on and view the ocean and boats sailing by. The second bedroom has 2 full beds and the third bedroom has a set of bunks and pull out twin bed below the bunks. Our home can accomodate 9 people. in bedsbrThe kitchen is fully stocked for entertaining with a balcony/deck that comes off the kitchen and dining room for access to the pool below.brWe have a ping pong table, beach chairs, beach cart ,towels, beach toys /floaties. A front load washer and dryer are provided. brThis is our wonderful home and we would love to share it with your family as a splendid get- together or snowbird rental for the winter season ! brbrKeywords: Quiet home at the end of a private street with 3 car garage and fantastic views of the water! Please contact us with any questions - we are available at 941-626-2625 Read More

  • Property-20 Image 1
    Canal Front Townhome W/ Screened Patio, Fast WiFi, Washer/Dryer & Central AC
    Private Vacation Home $211 / Nightly
    • 2 Bed
    • 2 Baths
    Longboat Key, Florida, United States

    Longboat LovebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThere is nothing quite like slipping into the coastal mindset of Longboat Key, so make your way to this delightful getaway and relax in style. Longboat Love will have you smitten in no time with the bright interior, canal views, two-story layout, and screened porch! Both bedrooms are located upstairs, so there will be a division of entertaining and getting some rest that will come in handy with night owls that want to stay up and reminisce downstairs. Each morning, you can start the day on a tasty note with a cup of coffee and a hearty breakfast whipped up in the full kitchen boasting stainless steel appliances, stylish subway tile, and all of the utensils needed for favorite recipes. When it is time to settle down after full days at the beach, throw sandy suits into the private washer and dryer, and kick back in the living room for a movie night! The plush sofa, free WiFi, and flatscreen TV will provide more than enough. comfort and entertainment. brbrThings to KnowbrFree high-speed WiFibrSnowbird-friendlybrbrThis property is managed by Vacasa Florida LLC.brbrParking notes: Two vehicles can fit onto the driveway.brbrDock details: Guests can stand, sit, or fish on the dock. Due to multiple factors beyond Vacasa's control, we cannot guarantee a safe docking of any water crafts.brbrbrbrDamage 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.brbrbrCity/town permit number: 12238brState/province permit number: CND5105556 Read More

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Information about vacation rentals in Longboat Key

houseNumber of available properties in a Longboat Key

627 properties

pricePrices starting from

$68.00

petsNumber of properties with pets allowed

86 properties

spaNumber of properties with pool/spa

540 properties

kidsNumber of Children welcome properties

577 properties

beachNumber of properties near beach/ocean

504 properties

Most popular vacation rentals in Longboat Key

  • thumb
    $ 256.00 avg/night
    2
    • 1 Beds
    • 1 Baths
    • 4 Guest(s)
    230 ONE-BEDROOM - Diplomat Beach Resort Longboat Key, Florida, United States

    Escape to paradise! Brand new furnishings! After shelling, sightseeing or doing "nothing" at... Read More

  • thumb
    $ 492.00 avg/night
    2
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    LaPlaya 101A - Step out to the beach from your screened lanai. Light and bright end unit. Longboat Key, Florida, United States

    Beachfront 2 Bedroom, 2 Bath condo in the center of beautiful Longboat Key, an island just a few... Read More

  • thumb
    $ 304.00 avg/night
    3
    • 2 Beds
    • 1 Baths
    • 4 Guest(s)
    FALL SPECIAL !LaPlaya 102E-Tropical garden view near the pool! Longboat Key, Florida, United States

    2 Bedroom & 1 bathroom, groundfloor condo just steps to the beach or sheltered pool. Fully... Read More

  • thumb
    $ 368.00 avg/night
    4
    • 2 Beds
    • 2 Baths
    • 6 Guest(s)
    Sea Grape Inn #3 - BEACHFRONT Property Longboat Key, Florida, United States

    *Need to stay less than the minimum required nights? Please call the office at 941-383-2105.... Read More

  • thumb
    $ 275.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 6 Guest(s)
    Stunning sunset views; Beachfront condo on central Longboat Key Longboat Key, Florida, United States

    Private Condo located on second floor at Tiffany Plaza on Longboat Key. Second floor accessible... Read More

  • thumb
    $ 750.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    Beautiful Longboat Key Beachfront Condo Longboat Key, Florida, United States

    Relax, unwind, and enjoy the magnificent views of the pristine white sandy beach and the azure... Read More

  • thumb
    $ 275.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 0 Guest(s)
    Mable's Place ~ A Historic "Old" Florida Cottage Longboat Key, Florida, United States

    “Mable’s Place” is a historic beach cottage within walking distance of the Gulf of Mexico.This... Read More

  • thumb
    $ 238.00 avg/night
    3
    • 0 Beds
    • 1 Baths
    • 2 Guest(s)
    253 STUDIO - Diplomat Beach Resort Longboat Key, Florida, United States

    Beachfront studio unit with amazing ocean views. Completely remodeled with new furniture,... Read More

  • thumb
    $ 111.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    Longboat Key Tropical Beach Retreat Longboat Key, Florida, United States

    Seaplace on Longboat Key is a tropical oasis where you can relax on pristine white beaches. This... Read More

  • thumb
    $ 232.00 avg/night
    3
    • 1 Beds
    • 1 Baths
    • 4 Guest(s)
    Beachcomber unit 403 Longboat Key, Florida, United States

    Our building is located on the beach, this unit has an ISLAND view. Beach front units are... Read More

 

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