Vacation Rentals By Owner In Longboat Key, FL

$729.98

Bright and Sunny Oceanfront Villa With Pool + Lanai | Hosts 6

Longboat Key, Florida, United States

Welcome to your private slice of paradise on the coveted Longboat Key. brbrNestled beachfront, this two-bedroom villa offers barefoot luxury, breezy interiors, and a peaceful atmosphere that instantly slows the pace. brbrWhether you’re here for a family getaway, a quiet reset, or just to listen to the waves with coffee in hand, this sun-drenched retreat delivers serenity in every square inch.brbrThis single-level villa is beautifully designed with a soft, coastal palette—think ocean blues, natural textures, and timeless whitewashed wood tones. Inside, the open-concept living and dining area is filled with light and laid-back elegance. Rattan details and beach-inspired accents give the home warmth and character without ever feeling overdone.brbrThe kitchen is fully equipped for casual meals, post-beach snacks, and all the little moments in between. Whether you’re prepping pancakes or mixing margaritas, you’ll have everything you need.brbrThere are two serene bedrooms—one with a king bed and the other with two doubles to accommodate up to six guests. The two bathrooms are clean, simple and stocked with all the essentials (yes, including fluffy white towels).brbrThe private lanai opens directly to the pool, just steps from the sand. Enjoy your morning coffee in a quiet breeze, take an afternoon dip, or linger outside for sunset cocktails—every day here begins and ends with the ocean as your backdrop.

2

Bed

2

Bath

6

Sleeps

$380.44

/ Nightly

Condo

Ocean Breeze: Open Next Thursday & Friday!

Longboat Key, Florida, United States

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!brbrUpon arrival to Silver Sands Gulf Beach Resort, you will be wowed by the tropical property! Conveniently located in the middle of Longboat Key, and just off the main road, Gulf of Mexico Drive, this small, intimate resort, only 35 units, has so much to offer: direct, private beach access, heated pool, loungers and sun umbrellas, laundry facility, mini golf course, shuffleboard, and complex office with staff.brbrWhen you arrive, pick up a parking pass from the main office (onsite staff 9A.M. - 5P.M. daily for any questions). There are also two in the condo, just in case! Then make your way to our condo, Unit 256, located on the second floor for optimal sunset viewing! The condo has a smart lock for easy entry and exit. Each guest is assigned a secure, individualized 4-digit code (deleted upon departure!), allowing for 24/7 arrival and freedom from carrying a key when on the beach...! brbrUpon entering, our condo features a spacious bedroom with king-size bed and Smart TV with cable too for viewing while lounging. There is a large closet and chest of drawers for storing belongings for a long stay, especially if you are a snowbird escaping those bitter winter months up North...!brbrWalk further, and you reach the living room with ample seating and queen-size sleeper sofa, which is just perfect for extra members of your party - the little ones! There is a Smart TV with cable for entertainment, when you're not on the beach, plus a variety of reading material, board games, and children's toys. Wifi, of course, is available throughout!brbrThere is full heating and air conditioning within the condo, plus a ceiling fan in the living room and extra floor fan in the closet!brbrFor convenience, we have a Pack 'N Play, for families traveling with infants!brbrThe living room flows into the fully stocked kitchen (coffee makers - drip and Keurig, blender, wafflemaker, Tupperware, wine glasses, etc.), with dishwasher, including everything you might need for a quick weekend trip or a month-long stay.brbrThe bathroom features a combined tub and shower, which always comes in handy when traveling with children!brbrBeyond the main living space is a large, screened lanai with patio furniture, ideal for eating a meal or sipping a cocktail! We have a deck box filled with fun beach toys for the kids too!brbrOn property, there is a large heated pool with deck, featuring lounge chairs. Pick up a beach umbrella and walk to the West (no need to cross a busy street!) to reach the private beach with more lounge chairs. No need to bring your own!brbrThe best part of our condo is the pool/ocean view, ample space, and all of the amenities that Silver Sands has to offer, most importantly, easy and quick beach access!brbrNotes:brbr1. Upon arrival, the condo will be prepared with fresh bed linens, bathroom towels, and beach towels. brbrThere will also be starter supplies of the following:brbrBathroom:br- toilet paperbr- shampoo & conditionerbr- body washbr- hand soapbr- hair dryerbrbrKitchen:br-paper towelsbr- spongebr- dish soapbr- dishwasher detergentbr- garbage bagsbr- olive oilbr- spicesbr- aluminum foilbr- plastic storage bagsbr- cleaning spray br- coffee filters (drip & Keurig!)br- ice cube traysbrbrCloset:br- iron & ironing boardbr- laundry detergent, on-property credit-card operated laundry, $2/wash, $2/drybr- extra folding beach chairsbr- sun umbrellabr- beach wagonbr- vacuum cleanerbr- broom and dustpan - in utility closet!brbrDaily housekeeping service is not available unless you would like to request a mid-stay clean for an extra fee, which I can arrange for you...! Sometimes that can come in really handy!brbr2. For our condo, there is one parking spot available - park wherever you like within the lot! Due to the size of the parking lot, unfortunately, no guest cars or trailers can be accommodated. Upon arrival, please ask the main office for a parking pass to be displayed on your dashboard. If you arrive after the office is closed for the evening, we have two laminates passes in the condo too!brbr3. Please note our condo is best suited for one-two adults or one-two adults plus one-two children in the sleeper sofa, and/or one in the Pack 'N Play, if needed. Unfortunately, we cannot accept reservations for over two adults. If it is a unique situation, feel free to message me to discuss further. Thank you for your understanding!brbr4. The condo is located on the second floor... for a pool/ocean view! At the complex, there are stairs, but no elevator.brbr5. The entryway door opens into the bedroom; this is very typical for Longboat beach hotels.

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$409.13

/ Nightly

Condo

Outrigger Resort #10 by RVA

Longboat Key, Florida, United States

RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger Resort. The Outrigger grounds offer coin-operated laundry facilities, BBQ areas, and direct beach access. Relax by the heated community pool, take a stroll along the romantic beaches, or enjoy a short drive to the world famous St. Armand's Circle. This one-bedroom, one-bath Gulf front end unit offers beautiful decor and relaxing views. Relax on your private screened patio and escape to paradise.brbrbrbrAccommodations: One-bedroom, One-bathroombrbrbrbrAmenities: Private Patio, Grill, Full-size Kitchen, Wireless Internet, Community Pool, Washer/Dryer, On the Beach, Private Beach AccessbrbrbrbrLocation: 5155 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King + Sleeper SofabrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Restrictions: 7 Nights; Contact our local team for shorter stay options

1

Bed

1

Bath

4

Sleeps

$306.73

/ Nightly

Private Vacation Home

Bay Breezes 2BR / Pet-Friendly Cedars East RVA

Longboat Key, Florida, United States

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public, it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #830 Accommodations: 2-bedroom, 2.5 bathroom town home with bay views from your private patio.brbrbrbrUnit Amenities: Nicely Decorated, Flat Screen TVs, Wireless Internet, Full-size Kitchen, Private Lanai, Fitness Facility, Community Pool, Beach Access (A Short Distance Away)brbrbrbrLocation: 830 Evergreen Place, Longboat KeybrbrbrbrView: Bay ViewbrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrMinimum Night Requirements: Minimum Stays Apply

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Bath

Sleeps

$338.91

/ Nightly

Private Vacation Home

Arts & Vines: LBK Pool Spa Dog Friendly by Anna Maria Life Vacation Rentals

Longboat Key, Florida, United States

This home requires a 28-night minimum stay.brbrArts and Vines by Anna Maria Life Vacation Rentalsbr6836 Pine St, Longboat Key, FL 34228brbrWhat You'll Love About This Home:brLocation! Beautiful Longboat Key!br3 Bedrooms / 2.5 BathroomsbrKing, Queen, 2 Twins, Full Sofa BedbrPrivate Heated Pool & SpabrPool LoungersbrCovered Poolside Lounge with Patio DiningbrRooftop Deck with Lounge SeatingbrGas GrillbrOutdoor Balcony DiningbrMultiple Decks Overlooking Lush Backyard & PoolbrFenced YardbrDog Friendly - with fee. See below. Max 2 small dogs.brProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach TowelsbrParking for 5 CarsbrbrDetails:brLocated on Longboat Key's barrier island, with gorgeous, peaceful, quiet beaches offering soft white sand, turquoise water, and dramatic sunsets, Arts & Vines radiates a vibrant, artistic vibe showcasing bright, beach themed artwork throughout. Our art-filled retreat is welcoming and full of character. Step inside and feel like you are walking through a beachside gallery full of color and personality.brbrThe main level features a beautifully integrated kitchen, dining, and living area that blends modern elegance with a warm, coastal flair. Bright, breezy, and full of life, it's made for gathering, creating, and enjoying the Florida lifestyle. Whether sipping morning coffee or hosting a sunset dinner, it invites comfort and conversation. Wall-to-wall windows and glass doors frame lush greenery, making you feel as though you're dining in a tropical treehouse. With sliding glass doors opening to the outdoor patio, guests will enjoy this space designed for dining, lounging, and soaking in the lush, tropical surroundings.brbrThe bedrooms exude peaceful serenity. The primary suite is a peaceful retreat tucked away on the second floor. Featuring a plush king-sized bed, the room is bathed in natural light from large windows overlooking lush greenery. A sleek ceiling fan and wall-mounted TV provide comfort and convenience, while the ensuite bathroom offers a private spa-like experience, complete with modern finishes and thoughtful touches. Charming and cozy, the guest bedroom features a comfortable queen-sized bed with soft bedding and tranquil decor. Brightened by natural light and accented with coastal details, the space includes a flat-screen TV, making it a perfect haven for relaxation after a day at the beach. The third bedroom offers two twin beds, ideal for kids, friends, or additional guests. Light and airy, the room includes a TV and playful coastal accents that reflect the home's beachy personality. It's a welcoming and comfortable space for winding down and recharging. For added convenience, there is a full sized sofa sleeper.brbrThe rooftop deck is a private oasis—an inviting retreat perched above the treetops, blending comfort, style, and nature in perfect harmony. With cozy wicker lounge seating under a modern pergola and plush cushions for relaxed conversation, it's the ideal setting for evening gatherings or peaceful morning moments. The open-air section features a pair of loungers and a café table, perfect for soaking in the sun or enjoying a glass of wine under the stars. Surrounded by lush greenery and cooled by coastal breezes, this tranquil perch invites relaxation, reflection, and a deep connection to nature..brbrThe covered poolside dining area offers the perfect blend of comfort and tropical ambiance, ideal for relaxed outdoor living. Featuring a spacious dining area with seating for eight, it invites al fresco meals and sunset cocktails surrounded by lush greenery. Just steps away, the private pool shimmers invitingly, framed by tropical landscaping and complemented by a paved deck with loungers—perfect for sunbathing or a peaceful afternoon by the water. The hot tub offers a perfect spot for relaxation, allowing guests to unwind in warm, bubbling water after a day of exploring. Whether you're entertaining or unwinding, this outdoor retreat is designed for pure vacation bliss.brArts and Vines is a dog friendly home! If you have added a pet to your reservation under the number of pets, the fee of $150 per dog plus tax has been added to your reservation total. Please note, there is a 2-dog limit. Small Dogs Only.brbrIf you are looking for Gulf breezes, peaceful ambience and total relaxation, Arts & Vines is the perfect vacation spot for you.brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - Queen Bed, TV - Floor 2brBedroom 3 - Two Twin Beds, TV - Floor 2brFull Sized Sleeper SofabrbrPlease note:brThis home requires stays of at least 28 nights.brAmenities are subject to change.brSmall Dogs Only - 2 maxbrDriveway parking is available for a maximum of 5 cars. Parking for additional vehicles is not available.brGarage is not available for guest use.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than 28 nights. The maximum occupancy is six. brRRR-00499 brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

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Bath

Sleeps

$264.46

/ Nightly

Condo

Fantastic Beach Condo

Longboat Key, Florida, United States

A one minute walk to the spectacular beach on the Gulf of Mexico, with sunshiny days and gorgeous sunsets! The complex offers a junior Olympic pool, hot tub, baby pool, direct beach access with chairs and umbrellas provided for you, tennis, pickle ball, ping pong, weight room, aerobic room and grills throughout the property. Seven minutes from fantastic dining and shopping and fun on St. Armands and fifteen minutes from downtown Sarasota.

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Bath

Sleeps

$506.66

/ Nightly

Condo

Sea Grape Inn #2- 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, Screened Lanai w/ocean & pool view. Check our online Reviews!brbr** Need to stay less than the minimum required nights Please contact us **brbrThe Sea Grape Inn is a boutique-style resort complex, located on the shores of the Gulf of Mexico, on Longboat Key with 8 beautiful condos in a beachfront location. A perfect beach getaway!brbrBEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. brbrBeautifully appointed 2 bedroom 2 bath condo, on the first floor with a screened lanai that jets out from the living area where you have a view of the pool and the Gulf of Mexico and features a flat screen TV. brbrTile throughout with a king bed in the primary bedroom and flat screen TV as well as a view of the water. The guest bedroom has two single beds as well as a flat screen TV. Each bedroom has their own private bath. Both baths have been upgraded to include new vanities, toilets and tile. brbrThe kitchen has been upgraded and includes granite counter tops and is fully equipped just like home. The new living room furniture offers a sofa bed.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.brbrGetting around the island is best by car.brSee house manual in rental

2

Bed

2

Bath

6

Sleeps

$340.38

/ Nightly

Condo

Oceanview Beautiful Penthouse 3 Rms Private Patios Spacious Steps to the Beach

Longboat Key, Florida, United States

* DISCOUNTED RATE AVAILABLE FOR MORE THAN 90 DAYS. CONTACT OWNER FOR DETAILS*brLife is good at Beach Harbor Club in Longboat Key. This penthouse has 3 rooms, 2 full bathrooms and one half bathroom. It offers breathtaking views of the bay from all Bedrooms and Living room. Two private patios with ocean view, one with view of the bay and gulf. A few steps to the beautiful beach. The condo is newly remodeled and updated. New kitchen, fridge, microwave and dishwasher. Big dinning/living area. Two flat tvs, one on the living room and the other on the master room. Updated bathrooms. Master suite has tube shower. Upgraded cable, wifi internet and phone. Kitchen is fully equipped. Community has nice gym, heated pool, BBQ area. This is a beach to bay community. Private beach with beach chairs and umbrellas. Community kayaks in the Bay Area. Fishing area in the Bay Area. Business center. brMinimum Rental of this unit is 3 months. br*DISCOUNTED RENT AVAILABLE FOR MORE THAN 90 DAYS RENTAL. MESSAGE OR CALL OWNER (JP) FOR DETAILS: (4077059323). br** Additional fees:br1. $220 cleaning fee.br2. $100 HOA application fee. br3. Rental tax 12%br4. Refundable Deposit $500. br

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Bath

Sleeps

$519.47

/ Nightly

Condo

Sea Grape Inn #6- Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbr** Need to stay less than the minimum required nights Please contact us **brCheck out our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex, located beachside, on the shores of the Gulf of Mexico, on Longboat Key. A perfect beach getaway!brbrBEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbrCompletely renovated stunning BEACHVIEW condo! Totally re-done and upgraded condo, located directly on the Gulf of Mexico Beach--with beautiful, uninterrupted views of the ocean. brbrThis GORGEOUS 2nd floor 2 BD/2 BA condo has been totally renovated, with you in mind. A completely updated kitchen--featuring new cabinetry, stainless steel appliances, beautiful quartz counters, new oversized sink and faucet, plus a fully stocked kitchen. All the amenities of home! brbrDecorated to reflect the casual upscale beach lifestyle which will be yours during your stay, lounge in the living room which includes a flat screen TV, a new sectional sofa with queen-sized pullout bed, and an upscale recliner chair. Plenty of dining room seating including 3 breakfast bar chairs to accommodate all your family meals.brbrRelax on outdoor seating in the screened lanai while taking in the view of the private pool, and tranquil waters of the Gulf of Mexico. Finish your day watching the spectacular sunset, either from your private lanai or beachside. brbrThe primary suite offers a luxurious king bed, flat screen TV, and a recently remodeled private bathroom, complete with plenty of storage, new bathroom fixtures, updated shower and tile throughout. The second bedroom suite has two twin beds, a flat screen TV and a recently remodeled private bathroom, also with plenty of storage, new bathroom fixtures, updated shower/tile.brbrBeautiful tile floors throughout, freshly painted, loads of storage, furnished in casual, upscale beach elegance. brbrYou have certainly discovered the perfect beachside getaway–the setting for a relaxed family beach vacation, a fun friends getaway, or a romantic stay for 2. We can’t wait to welcome you.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

$498.0

/ Nightly

Private Vacation Home

4-bedroom house on Longboat Key with beach only 150 yards away.

Longboat Key, Florida, United States

Make yourself at home in this large recently remodeled 4-bedroom 3 bathroom Longboat Key retreat with 1 king bed and 3 queen beds, this house offers a perfect blend of comfort and style, relax in the large family living space with 65 inch tv and a pool table or take in the fresh beach air on the outdoor patio with plenty of seating and a gas bbq. Plenty of off-street parking. Guests also have free access to Cedars East Tennis resort during their stay (no additional fee) - tennis/pickleball/pool/bar/restaurant and bike rental! Within 200 yards of the house there is a cafe and a deli, 3 pub/restaurants, a pizzeria and a local beach shop.

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Sleeps

$333.64

/ Nightly

Private Vacation Home

Piece of Paradise

Longboat Key, Florida, United States

Located on a most welcoming friendly street. This house with 3 bedrooms & 3 full bathrooms sits on a canal with dock and large paved area. Just a short 5 minute walk to the beach and Gulf of Mexico with its amazing sunsets. The perfect place to come and relax on the back open patio with a high top table or on the dock itself with seating. The front patio with seating is partially enclosed if you need a break from the sun and also where the grill is located.brbrThis contemporary home is all renovated with all updated stainless appliances. The perfect place to come and relax. House is well stocked with all the essentials you need inside as well as beach supplies, such as beach towels, beach chairs and a cart to haul all your beach needs, as well as fishing poles and supplies to try your luck fishing off the dock.brbrThe home is a short walk to relaxed and upscale restaurants and Durante Park or a short drive to St. Armands Circle that is full of restaurants and shopping.

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Sleeps

$303.45

/ Nightly

Condo

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Longboat Key, Florida, United States

RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium complex. New designs were created using South Beach flair, resulting in comfortably modern furnishings and decorations. Located directly on the beach, this resort features beautiful Gulf-front views, which means you are only steps from the white-sand beaches and placid turquoise waters and memorable sunsets that will have you daydreaming about your next beach vacation month after month. All units feature a full-size kitchen or kitchenette with stainless steel appliances and granite countertops, and private patio or balcony (2 brdms only). Whether you are traveling as a family, honeymooners, on business or just want a resort with the best accommodations Longboat Key has to offer, this is the resort for you.brbrbrbrAccommodations: The Beach on Longboat Key is a relaxing, yet modern retreat located directly on the Gulf of Mexico, located mid-island on Longboat Key. Choose from our various unit styles including studio, hotel, one- and two-bedroom units. Enjoy all the amenities of home in these fully furnished condominiums including LCD, flat-screen TVs, full-sized kitchen or kitchenette with stainless steel appliances and granite countertops, dining area and modern, yet beachy, décor.brbrbrbrResort Features: On-site Office, Heated Swimming Pool, Private Beach Access, Wireless Internet Access, Complimentary Chaise Lounge Chairs and Umbrellas, Fully Equipped Kitchens or Kitchenettes, Picnic Area, Private Patio or Balcony (2 bdrms only), Designer Decorated Units, Complimentary Parking, Community Laundry Facilities (private washer/dryer available in select units), Outdoor Shower, Various ViewsbrbrbrbrUnit #106 Features: Studio unit including new furnishings, a full-size kitchen, private patio, and Gulf-front viewsbrbrbrbrView: Gulf ViewbrbrbrbrBedding: 1 Queen Murphy Bed

1

Bed

1

Bath

2

Sleeps

$258.42

/ Nightly

Condo

Seaplace on Longboat Key

Longboat Key, Florida, United States

The Unit:brNewly renovated and fully furnished 2 bedroom and 2 bathroom condo. Located on beautiful Longboat Key on the Gulf of Mexico. This getaway is your perfect home away from home and provides everything you need to enjoy a relaxing island lifestyle.brbrMaster bedroom features a queen sized bed, plantation shutters and a walk in closet.brbrGuest bedroom has a queen sized bed and a private bathroom with a walk in shower.brbrThe private screened lanai is the perfect spot to sip your morning coffee while enjoying the partial gulf views, or watching one of the many spectacular evening sunsets over the gulf.brbrThere are 3 flat screen T.V's, cable and WiFi is included. The fully equipped kitchen with quartz countertops is perfect for cooking an evening meal when you do not feel like dining out. Kid friendly. There is 1 reserved parking spot for the unit and plenty of guest parking. Smoking and pets are not permitted. brbrA 30 day advanced notice is required for reservation. brbrResidential Rental Certificate # RRR-00116.2023brbrThe Complex:brBeautifully landscaped 43 acre gated community located on the Gulf of Mexico in the town of Longboat Key. 24 hour security, newly remolded clubhouse with fitness center. 1/2 mile of beautiful white sand private beachfront. 2 swimming pools, 2 spas, kiddie pool, 3 Har-Tru tennis courts, playground and BBQ grills. Beach chairs and umbrellas available free of charge at a first come first serve basis. brbrThe Area:brA short drive to Publix, St. Armands Circle and downtown Sarasota. The island features plenty to do including fantastic restaurants, bike, boat and jet ski rentals.

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Sleeps

$108.96

/ Nightly

Condo

Magnificent gulf front condo with beautiful white sand beach

Longboat Key, Florida, United States

Magnificent direct Gulf front property on Longboat Key. The condo has been updated from furniture and furnishings to paint and décor. Tastefully presented, this first floor home offers a spacious Master bedroom suite complete with tile bath walk in closet and sliders which open to the sights and sounds of the Gulf and flat screen TV. A large formal dining room and open living room are perfect for entertaining or just enjoying the view of the pool and white sand beach or those beautiful South Florida sunsets. A bright breakfast room adjoins the fully equipped kitchen. The guest suite blends bright colors and textures with relaxing furnishings. The bath boasts a walk in full tile shower with new fixtures. A large walk in closet rounds out the suite. Enjoy quite moments on the lanai and relax in the warm tropical sun by the heated in ground pool. Conveniently located at the North end of Longboat Key and one of just 28 units, this home provides all the amenities of much larger complexes while maintaining a quiet decorum. Walk to fine dining on the Key or just a short 15 minute drive to St Armand's Circle. Off street parking along with laundry and mail delivery on site. High speed internet, phone, cable and all the furnishings you will need to enjoy all that the area has to offer is right here.

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$273.98

/ Nightly

Condo

Longboat Key Club!! Direct Beachfront!!

Longboat Key, Florida, United States

Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maximum of four adults. Your private community includes lush tropical landscaping and the white powdery beach sand that the Longboat Key is famous for. Only minutes away from Saint Armands Circle, Sarasota and Anna Maria Island. This gorgeous property being offered for rent by Licensed Florida Real Estate Broker Owner at a discount of 70% to 85% off of the non changeable, non refundable Hotel rate.

1

Bed

1

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4

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$435.05

/ Nightly

Condo

Beachplace Oasis on the south end of Longboat Key

Longboat Key, Florida, United States

Newly renovated! Open and airy, seamless flooring runs throughout the unit with a mid-century modern design. Bright living space with comfortable sectional sofa, Stressless recliner, shiplap ceilings, and flat screen tv adjoins the open dining room with table seating for six. A wall of windows and sliding door to the balcony make the Florida views the focus of this space.brbrThe kitchen has been newly renovated with adjustable task lighting, new appliances, Green Pan cookware, and peninsula seating. Split floor plan has two bedrooms, each with an adjoining bath. The primary bedroom has a king bed, flat screen tv, and balcony access; its private bath has a large dressing area with adjustable can lighting, dual vanities, professionally installed grab bars, enclosed w/c and walk-in shower. The secondary bedroom can be configured as a king bed or two twin beds and has a flat screen tv and an adjoining bathroom with a tub/shower combo (this bedroom will be configured as a king unless the twin beds are requested). The living room and both bedrooms have new ceiling fans with dimmable lights. brbrThe balcony offers a tranquil space for morning coffee, evening sunsets, or working from home overlooking the pond full of turtles, jumping fish, and shore birds.brbrA private staircase from the balcony leading to the walking path around the pond provides quick and easy access to and from the pool, gym, and beach in addition to the building's shared elevator.brbrBeachplace amenities include a heated pool with lap lanes, a large hot tub, a covered wading pool for small children, clubhouse fitness center including weights and cardio, lighted tennis and pickleball courts, and a 31 acre campus with prime Gulf of Mexico sugar sand beach frontage. Walk uninterrupted for miles along the beautiful white sand beach! Beach amenities include loungers, chairs, and umbrellas for Beachplace residents and guests. Gas grills, ping pong, corn hole and a lending library are adjacent to the pool area. Gas grills, a car wash area, and electric car charger are available at the tennis courts. brbrThis unit includes two parking spaces, a reserved covered parking space plus one outdoor space, and extra guest parking is also available. Carts are available to help you with unloading suitcases or groceries, easing your arrival. Unit amenities also include a large storage closet for luggage, with puzzles, games, extra beach towels, ironing board and iron, and a Dyson stick vacuum for easy cleanups. brbrRestaurants, shopping and frequent art fairs are minutes away at St. Armand’s Circle. Rent a kayak and paddle the mangrove tunnels at Ted Sperling park and find manatees or dolphins, depending on the season. Strolling sarasota's bayfront park, downtown farmer’s market or Marie Selby Botanical gardens are great off-island activities just a 15 minute drive over the bridges.brbrMinimum lease is 30 days - units may not be sublet. Occupancy may not exceed 4 persons for this unit. Per HOA rules, leases can be made to individuals or married couples, additional occupants are considered guests, and guests may not occupy the unit when the lessees are not in residence. Your reservation requires the completion of a Beachplace Association application that must be accepted 10 days prior to arrival; application fee is $165. No smoking, candles, parties, or pets are allowed. Guests should be called in to the security guardhouse before their arrival. Check in is 3pm, check out 11am ( we’ve created a later check out so you can enjoy a last soak in the hot tub or stroll on the beach - we know how hard it is to leave!)

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$174.21

/ Nightly

Condo

Gulf Front Luxury - Serenity Sunset - Long Boat Key, FL

Longboat Key, Florida, United States

Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upscale, direct waterfront luxury condo. This 2nd floor end unit has incredible unobstructed views of the gulf---- direct views from living area and both bedrooms. Our condo boasts a full length, gulf front lanai with sliding doors from the master bedroom and living room. The second bedroom has its own gulf front lanai with sliding doors. Watch the playful dolphins frolicking in the gulf with your morning coffee. Experience the most magnificent sunsets every night from the lanais. This unit is truly paradise!brbrThis condo has been renovated with a state of the art kitchen -- stainless steel appliances and granite counter tops. Bathrooms boast over sized showers and custom tile work. A sleeper sofa in the den accommodates extra guest. Flat screen LCD TVs are located in the living room and both bedrooms. High speed internet, air conditioned, handicapped access. In unit washer and dryer for your convenience. brThis is Florida living at its best!!!brbrLocated in a well maintained Portobello condo complex, amenities include a beautiful private beach, heated pool, tennis court, barbeque grill, assigned parking and club house. Community boat dock, canoe dock and picnic area is available. Minutes to St. Armand's and Sarasota. One-half mile to Publix/CVS Shopping Plaza. Two miles to the new 5 star St Regis Hotel. World class fine dining minutes away, One mile from Bayfront Park for pickle ball, kayaking, playground and more. 10 mile bike path on Gulf of Mexico Drive.

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Bath

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$351.67

/ Nightly

Condo

First level - steps to beautiful beach, Longboat Key

Longboat Key, Florida, United States

brFirst level - steps to beautiful beach, Longboat KeybrThis condo is located on gorgeous Whitney Beach, at the north end of the barrier island Longboat Key. It is a ground floor unit with easy access to the pristine white beach and pool area. No stairs - just step right outside. Very beautiful and peaceful. brbrThis lovely 1 BR condo offers a spacious living room, kitchen, a master bedroom, a large bathroom and washer/dryer. The master bedroom has a queen bed. Free wireless high speed Internet, TV, and cable. There is a TV in the living room and another TV in the bedroom. Linens and towels are provided. This roomy condo is 1 300 sq. ft. or 120 m2. It has a private patio which overlooks the turquoise waters of the Gulf of Mexico. brbrThe long white sandy beach is just steps away. Chaise lounge chairs available for your convenience. There is a heated pool and tennis/pickle ball courts. Beautiful grounds with tiki huts, barbeque and shuffle board. Bike path along the entire length of Longboat Key. Close by you have Bay front park with open play pickle ball courts.brbrGreat restaurants and shopping nearby. Across the street you'll find Whitney plaza. A quaint little plaza with several places to eat, a bar, a liquor store, a hair salon, a 24 h gym, pilates studio, a kayak and stand up paddle board rental, a design gift store, and more.brbrThe barrier isle Longboat Key has been voted one of North America’s top islands by Condé Nast Traveler’s readers. Whitney Beach is located on the north end of the island. brbrApproximately 15-30 minutes from downtown Sarasota and the famous St. Armand’s Circle with restaurants, shopping and culture. brbrLongboat Key is your perfect paradise. brbrThere are activities and attractions for all age groups. Fishing, boating, jet skiing, para sailing, kayaking, biking, golf, tennis, snorkling, scuba, shelling, turtle watching and much more…brbrMote Aquarium, St. Armand’s Circle, Marie Selby Botanical Gardens, Van Wezel Performing Arts Hall, John and Mable Ringling Museum and Salvador Dali Museum. Busch Gardens in Tampa and only a two-hour drive to Orlando's theme parks.brbr30 minutes from Sarasota-Bradenton Airport and about an hour and a half from Tampa International.brbrWelcome to truly paradise on exclusive Whitney Beach, Longboat Key!brbrAdjacent 2 BR condo also available for rent. Please see VRBO Listing # 662700brbrWhether you're seeking a peaceful escape or an adventure-filled getaway, our beachfront condo offers the perfect blend of comfort and convenience. Indulge in the beauty of Longboat Key and create lasting memories during your stay.

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$534.66

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Private Vacation Home

Peacock Place LBK - Gorgeous 3-bedroom house in Longboat Key

Longboat Key, Florida, United States

Welcome to paradise! This tropical island retreat is located in a quiet residential area on the north end of Longboat Key. Walk to some of the island's best restaurants including Shore, Mar Vista, and Whitneys. Enjoy kayaking, paddleboarding, fishing and boating from the bayfront community dock and boat ramp. Best of all, take a short stroll to one of the most pristine beaches on the island, where you can enjoy sugar sand, clear blue water and breathtaking sunsets.brbr5 MINUTE WALK TO BEACH!!brbrThe upper level of the home is decorated in a casual beachy theme featuring a bright and airy living/dining area with a vaulted ceiling, skylights, and fireplace. The well appointed kitchen has a four seat breakfast bar and its own skylight. brbrThe outdoor areas of the home make it a true tropical paradise. Catch the ocean breezes and savor your morning coffee on the upper level patio surrounded by lush palm trees, as you enjoy watching local parrots, ospreys and peacocks. Down on the pool deck, bask in the Florida sun and splash or swim laps in the extra large pool, or soak your cares away in the attached jacuzzi. Grill out and enjoy outdoor living with family and friends in the covered dining area by the pool. Time to chill out The pool area also features an air conditioned cabana/rec room with large screen TV, refrigerator, seating area and full bathroom with shower.brbrRelax in the two spacious master suites decorated with breezy island flair. Each features a king bed, walk in closet and en suite full bathroom with tub/shower as well as a seating area with comfortable armchairs. The third bedroom has a full size bed, walk in closet and ensuite full bathroom with a walk in shower. All bedrooms have a large screen TV and views of the pool and garden areas.brbrAdditional amenities in the home include a full size washer/dryer, sand shower on the pool deck, and beach chairs and umbrellas. 5 minute walk to the beach with included beach cart.

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Bed

4

Bath

6

Sleeps

$274.53

/ Nightly

Apartment

The Blue Bungalow

Longboat Key, Florida, United States

Keep it simple at this peaceful retreat. Walking distance to the island’s best restaurants, it is perfect for couples, a solo getaway or a family of 3 or 4. Beach, eat, sleep, repeat at The Blue Bungalow.brbrThe spacebrA RARE FIND at this price pointbrThe Blue Bungalow is a newly renovated single story stucco with just a short walk to the beach, bay or numerous great restaurants.brbrUPGRADED BEAUTIFUL INTERIORbr65 inch rotatable 4k Samsung TV with super fast Frontier cable internet.brNEW cabinetsbrNEW appliancesbrNEW vanitybrNEW KING SIZE memory foam mattressbrQUEEN SIZE sleeper sofabrFULL KITCHEN with everything you need to prepare a meal.brOUTSIDE UNIT WASHER and DRYER dedicated to the unit (not shared)brPRIVATE SEATING area with gasbrgrillbrPOOL AVAILABLE a short walk away at Cedars East $20 a day for usebrbrGuest accessbrThe Blue Bungalow is equipped with games and books and beach equipment for your enjoyment. Feel free to use everything in our space.brbrOther things to notebrPlease, no smoking inside the Blue Bungalow.brNo pets for guests per HOA rule.brThe trash is on the street to the left.brYou can use the grill and anything in the shed. The key is on the key rack.brFULLY stocked with your groceries or personal touches upon arrival ***for a small fee.brDisclaimer: You are booking on a barrier island. That means beautiful beaches, peace and quiet. It also IS a barrier island. As such, the porch floods with a good rain. Though not often, but more often than the mainland, power and internet sometimes go out. Your hosts cannot control this and cannot give a discount for things we cannot control. If this occurs during your stay, we will make sure you have a small generator for your phones and basic needs and will communicate with you and assist you. If this happens during your stay, we also hope you will do what the islanders do and take the timebrto reconnect with loved ones or nature, read a book or play a game ( provided) or take a long walk on the beach. The island is a special place and its beauty and ruggedness in a storm are a part of that.

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