Home Vacation Rentals By Owner In Longboat Key, FL

Showing 720 Of 744 Vacation Rentals
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Exceptional(40)

$292.43

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Condo

On the beach, Sunset view, Monthly rental 2B/B2 Pool&Tennis

Longboat Key, Florida, United States

The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box, Nespresso coffee machine, flat screens TV's in every room (65 and 32 in bedrooms) and free WiFi. The Master bedroom has a King and the Guest bedroom a Queen and XL Twin. Two bathrooms and a well furnished kitchen, washer/dryer. You may sun, relax or walk for miles...shelling is outstanding. Several golf courses are nearby. Longboat Key, a barrier isle, is nestled between Sarasota bay and the Gulf of Mexico, voted #2 in the Condé Nast Traveler 2010 Readers' Choice Awards for Top Islands in North America. Whitney Beach is located on the north end of the island.brAll rooms have flatscreens TV's. In the bedrooms 32'' and in the living room 65. In the living room there is Bose Soundlink Bluetooth Mobile Speaker. You can enjoy your music wirelessly from your smarthphone, tablet, laptop or other bluetooth enabled device. Nespresso coffee machine in the kitchen, other coffee machines at your choice.brThe minimum stay for our condo is 30 days or one calender month. brLongboat Key Residential Rental Registry: RRR-00945.2013
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Exceptional(29)

$549.0

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Private Vacation Home

Longboat Key’s rare location!Beautiful canal front house with a private dock!

Longboat Key, Florida, United States

This wonderful, remodeled, neat unit has one bedroom king size bed with walk in closet and private bathroom, living room 2 pull out queen size sofas , dining area, kitchen and extra shower with toilet.brbrOutdoor living space , many ways how to relax, you can sit by the canal or by our newly build large heated pool that is shared with the other unit on the property. brIt has 2 gates and 2 separate areas for entering water.We provide lounge chairs, umbrellas etc. brbrNote: to heat the pool in the winter time - there is a charge of 180$ /week.brbrGreat porch with dinning area and lounge area basically sitting on the canal.Dock is just by the house, very nice vast garden and parking lot beyond the house. The house offers great privacy with beautiful views of the bay. A unique place where to spent your vacation! The house is fully equipped - beach towels and chairs,+umbrella are provided.brTV, WIFI and washer+dryer in the unit as well.brAlso you will be entertained by our pair of Manatees who love Boathouse so very much:)brbrLongboat Key's beach is lined with private homes, condominiums and rental properties that limit public access to the beach. There are a number of public beach access points on Longboat Key leading to the Gulf of Mexico beaches. There are 12 beach access points on Gulf of Mexico Dr.. None of the public beach access points have any facilities such as bathrooms, concessions or lifeguards. Although, there are restrooms at Bayfront Park parking area.brbrCabana Beach Resort accross the street is a private rental property and not a public beach access. Please use only public beach access points not Cabana’s .brbrAs you travel along Gulf of Mexico Dr. on Longboat Key, keep an eye out for the blue and white beach access signs along the side of the road. Some of the access points offer parking at the beach access point while others on Longboat Key offer parking nearby.brbrOur property is equipped with RING bell Surveillance device, located outside, by the entrance gate . brbrAll devices are installed for the security purposes.
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Exceptional(37)

$422.2

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Private Vacation Home

Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!

Longboat Key, Florida, United States

Welcome to Beach & Boaters Paradise a home in a residential community where you will have immediate access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. brbrPicture yourself vacationing in this beautifully remodeled home on fabulous Longboat Key - perfectly located on a deep water canal with a dock that can accommodate a 40+ foot boat, only minutes by boat to the Bay and less than two miles to the Gulf inlet. The deeded beach access is a short walk across Gulf of Mexico Drive. This 4-bedroom, 3.5-bathroom luxury waterfront vacation rental was designed to provide you and your family a lifetime of vacation memories to cherish.brbrThe dock-side screened patio has a large family-friendly heated pool and abundant lounging areas that invite you to swim the day away or just relax and read a book. Enjoy sunset dinners cooked on the built-in gas grill and dine “al fresco” at the outdoor dining table next to the pool as you watch the fish jumping by the dock!brbrThis one story home features chiseled travertine stone floors throughout. The spacious, yet comfy, great room has pocket sliding glass doors that open to the patio and maximize the outside water views. The high-end kitchen easily accommodates a large group with center Island, granite counter tops, stainless steel appliances and all the cookware you will need to make sumptuous meals!brbrThere are several amenities to make you feel at home including washer and dryer. The great room has a large screen smart TV with and a Blue Ray player and sound system. You can stay connected with friends and family with the free secure high speed wireless internet.brbrAll of the bedrooms were designed with comfort in mind. The master suite has a king size bed that overlooks the pool and canal. The elegant ensuite bath has dual sinks and an oversized shower. If you need the storage space, there is a huge walk-in closet. brbrThe second Master cabana suite features a queen size bed, adjoining full bath and French doors opening to the pool. The third bedroom has a king size bed and the fourth bedroom is furnished with a queen size beds. They are adjacent to the third full bathroom with tub and shower. brThe guest half bath is located just off the great room.brbrThe home has an open floor plan and will easily accommodate a family reunion-vacation or group of friends on an excursion. We invite you to be our guests.brbr[A word about Longboat Key: Longboat Key is a desired vacation spot because it has a laid-back feel with its sunny, pristine beaches. It is a residential community and the town requires a 30-day stay. If you want to visit local attractions or activities, they are close to our home. Some of our attractions include: St. Armand’s Circle (2.5 miles), downtown Sarasota shopping and restaurants (4.3 miles), Mote Marine Aquarium (1.7 miles), Marie Selby Botanical Gardens (5.6 miles), Van Wezel Performing Arts Hall (5.7 miles) or John and Mable Ringling Museum Complex (8.2 miles). The Sarasota-Bradenton airport is 8.5 miles.]br
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$132.4

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Condo

2 Bd/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico

Longboat Key, Florida, United States

Available from May 1, 2026 - December 12, 2026. Beautiful corner unit condo with an abundance of windows located between Sarasota Bay and across the street from the deeded Gulf of Mexico beach. The gated community complex has every amenity imaginable - four pools, tennis court, shuffleboard, kayak launch, and golf putting range. Residents will have access to the gym, sauna, poker room, ping pong, billiards, art studio, and woodshop. One bedroom has a king-sized bed, the second, two twin-sized beds and a queen inflatable mattress is available.brbrThe patio overlooks the boat canal to Sarasota Bay where you can lay on the sofa and read a book or sit and drink your coffee. There are TVs in each room and cable and wireless Internet are included.brbrThe owner can be reached by e-mail or phone if you have any issues during your stay. Additionally, there is an on-site management company available during business hours on weekdays.brbrSix miles to the south of Longboat Harbor is the lovely St. Armand's Circle with nice outdoor restaurants, shops, and great people-watching. Five miles to the north are Bradenton and Anna Marie Island with golf cart and scooter rentals, as well as beach-style eateries.brbrThe condo is a 25-minute drive from Sarasota Airport and a 70-minute drive from Tampa Airport. Uber and Lyft serve both airports, as well. There is one covered parking spot for the condo unit and guest parking is available. brbrThree bicycles can be used with the unit, as well as 2 lounge beach chairs and 2 short beach chairs. Bike paths are available throughout Longboat Key.
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Exceptional(1)

$121.99

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Villa

Waterfront Getaway Island Villa at Longboat Key

Longboat Key, Florida, United States

Relax or work remotely at our Waterfront Island Villa on LBK. Nestled 1 block from the beach & on Sarasota Bay, enjoy watching manatee & fish from your patio. Dock your boat behind the villa OR rent our private boatlift. Enjoy private beach access & use of our beach chairs, umbrella, wake/surfboards, towels, fishing poles & wine carrier for your stay. Durante Park, directly outside our front door, has a kayak launch, playground & bayfront trails. Rent for a month & share with your family/friendsbrThe spacebrThe villa has been freshly painted, updated and has been completely refurnished with island decor, original art and unique finds. The galley kitchen is equipped with a full refrigerator, stove, microwave, oven, confectioner oven, toaster, coffee pot and keurig cappuccino maker with a coffee bar! The cabinets are stocked with everything you need for cooking, as well as dinnerware, glassware, wine glasses and more. The open floor plan alots a water view from every angle of the dining area, family room, kitchen and reading nook. Even the private laundry room has a waterview. This unique 1 bedroom villa can comfortably sleep 4 with a pullout sofa in the living room. Guests will love the 2 recliners that overlook the waterview, but also where they can comfortably see the new smart 50 inch tv! ThebrThe island themed bedroom has a queen pillow top bed with plenty of pillows, a spacious dresser and a wall mounted smart tv. The walkin closet has enough storage for your clothing, golf clubs and more! Both the bedroom and family room have brand new air conditioning units with their own thermostats, as well as ceiling fans! The updated spa bathroom conveniently has a step in shower with a handicapped bar for those with balance issues. There is plenty of storage, stocked with soft towels, a hair dryer and essentials.brIf you have someone traveling with you that has mobility issues, (ie. A walker) they will love how easily accessible our villa is. We have 2 parking spaces directly in front of the front door. There is one small step to enter the front and one small step down to go to the back door. The back porch has cushioned chairs overlooking the water.brLastly, just in case any of our guests get too much sun and have to stay inside, we have games cards puzzles and of course free Wi-Fi so we can guarantee a good time for all!brGuest accessbrYou have access to the entire Villa, and to all of our beach toys and chairs in the storage facility on the side of the Villa. Directly in front of our villa door are 2 reserved parking spaces, making it easy for anyone who may be elderly or in need of easy accessibility to come inside. Guests can dock their boat in back of the Villa, which cannot exceed 21 ft. Our private boat lift is available to rent at an extra cost, which will fit a boat up to 26 ft.brOther things to notebrHandicapped Accessibility: our Villa is easily accessible to those who may be elderly or need assistance with walking with a walker. There is one small step up into the villa with parking available directly in front of the door and there is one small step down to exit the back door by the water. Also, the shower is a step in shower with a low ledge and a handicap bar. Some of the door frames may be tight for a wheelchair but would easily fit a walker.
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$340.83

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Condo

Beautifully remodeled condo with lots of amenities!

Longboat Key, Florida, United States

Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the flooring to the kitchen and baths, the decor is neutral with pops of color, giving the home a coastal urban vibe. The primary bedroom offers a king bed, walk-in closet with built-ins, and a desk. The primary bath has dual sinks and shower. The guest bedroom boasts queen sleeping accommodations and a TV. new luxury vinyl flooring throughout and gorgeous kitchen with stainless appliances, stone counters and lovely wood cabinetry. Outside your door you will find a bonus deck with chaises for sunbathing. This popular, Tim Siebert designed Gulf-to Bay community features 27 lushly landscaped acres, 4 Har-Tru Tennis Courts, a Jr. Olympic pool, kayak launch, bocce ball and fitness room in the clubhouse, and a gorgeous beach, located just across Gulf of Mexico Drive. St. Armands Circle is a short drive away, just over the Ringling Causeway you will find the vibrant downtown Sarasota arts and culture, as well as the many unique shopping and dining venues. Leases less than 7 months subject to additional taxes and fees.brbrPlease be advised that this property is currently on the market for sale, guests will be given reasonable notice for any showings.brbrFor additional details on Sarasota rentals and Longboat Key rentals contact Stephanie Deshaies at or email brbr***Information contained herein deemed reliable but not guaranteed***brbrAmenities Include:brbr- Bldg. Complex Name: Bayport Beach & Tennbrbr- Type Unit: Lowrise Condobrbr- Unit Rating: Goldbrbr- Beach Access Type: Walkbrbr- Distance to Beach: .10 Milesbrbr- Floor/Bldg Height: 2 of 2brbr- Year Built: 1983brbr- Approx. Sq. Ft.: 1,370brbr- Exposure/View: E/Greenspacebrbr- Pool/Spa: Communitybrbr- washer dryer: Yesbrbr- Parking Type: 1 Carportbrbr- Lanai / Balcony: Openbrbr- Master Bedroom: Kingbrbr- Bathrooms-Master: Showerbrbr- Guest Bedroom: Queenbrbr- Bathrooms-Guest: Showerbrbr- Flooring: Vinylbrbr- TV/Dvd/ Stereo: 2/0brbr- Internet Access: Wifibrbr- Listing Advisor: Stephanie DeShaiesbrbr- Min. Rental # x perYr: 30 x 12brbr- Security Deposit: $1,500brbr- Reservation Fee: $170brbr- Damage Protection: $60brbr- Application Fee Req.: $150brbr- Departure Clean Fee: $200brbr- Taxes: 13%brbr- Utility Charges: Includedbrbr- Rate - Monthly: $8,500/$4,250brbr
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Exceptional(22)

$520.83

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Condo

Sea Grape Inn #4- Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.br** Need to stay less than the minimum required nights Please contact us. **brCheck our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex, with 8 beautiful condos located beachside, on the shores of the Gulf of Mexico, on Longboat Key. A perfect beach getaway!brbrBEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.brbrA first floor 2 bedroom 2 bath condo that offers a view of the pool and Gulf of Mexico from the living area and the screened lanai which includes teak furniture. The primary bedroom offers a king bed and the guest bedroom offers a queen bed which has proven to be perfect for two couples with two larger beds and each having a private full bath. brbrBoth baths have been upgraded with new vanities, tile and toilets. The kitchen has been upgraded to include granite counter tops, newer sink and appliances. Tiled throughout and boast a tropical theme with Tommy Bahama furnishings. With the many paintings, sculpture and artistic touches that the owners have collected from throughout the world, this condo is truly an art lovers delight at the beach!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. brbr 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.brSee house manual in rental
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$327.03

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Condo

Beachplace 8-601 by FGC

Longboat Key, Florida, United States

Experience Coastal Elegance at Beachplace PenthousebrbrWelcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking panoramic views of the pristine beach, the shimmering Gulf of Mexico, and mesmerizing sunsets that paint the sky year-round.brbrStep onto the expansive wrap-around balcony and let the gentle sea breeze and stunning vistas captivate your senses. Floor-to-ceiling sliding glass doors seamlessly connect the balcony to both the living area and the primary bedroom, creating a harmonious blend of indoor and outdoor living.brbrInside, the residence has been meticulously updated with exquisite finishes that exude sophistication and style. Revel in the beauty of new impact windows and sliding glass doors, complemented by plank-style ceramic tile flooring that mimics the warmth of wood. The redesigned kitchen is a culinary masterpiece, featuring quartz countertops, a built-in pantry with pull-out drawers, a wine refrigerator, and a charming window over the sink offering city and gulf views.brbrThe primary suite is a sanctuary of comfort, complete with a walk-in shower with a sleek glass enclosure, and a vanity area for your convenience.brbrBeachplace is more than just a home; it's a lifestyle. Enjoy access to a Jr. Olympic-sized swimming pool with swim lanes, a splash pool, a hot tub, a state-of-the-art fitness center, a grilling area, tennis and pickleball courts, all within a secure 24-hour guard-gated community.brbrIndulge in the ultimate beachfront living experience at Beachplace Penthouse, where every day feels like a vacation.brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.
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$302.06

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Condo

Gulf Views & Cozy Comfort w Large Lanai Tern's Nest #22 Condo by RVA

Longboat Key, Florida, United States

Escape to paradise in this stunning Longboat Key condo, where every day starts with incredible water views and ends with breathtaking Gulf sunsets. brbrbrThis two-bedroom, two-bathroom retreat features an open and airy layout with plenty of room to relax. Step onto the spacious 26-foot screened-in lanai, your front-row seat to the Gulf of Mexico's blue waters and powdery white sand beaches—a perfect spot for morning coffee or evening cocktails. The large master suite opens directly onto your private Gulf-front lanai, creating a serene space for watching magnificent sunsets.brbrbrbrLocated in the charming Longbeach Condominium community, this retreat spans 17 lush, tropical acres on the north end of Longboat Key, blending Old Florida charm with privacy and tranquility. Yet, you’re just a short drive from the shopping, dining, and excitement of St. Armands Circle and the mainland. With a heated pool, direct beach access, and BBQ area, you’ll find plenty to enjoy here. brbrbrbrBook your stay and experience the tranquil beauty and unbeatable charm of Longboat Key!brbrbrbrAccommodations: 2-Bedroom, 2-BathroombrbrbrbrAmenities: Gulf Views, Full-size Kitchen, Large Screened Patio, Wireless Internet, Washer/Dryer on-site, Walking Distance to the Beach, Community Pool, Community GrillbrbrbrbrLocation: 7165 Gulf of Mexico Drive Unit #22, Longboat Key FL 34228brbrbrbrBedding: 1 King, 2 Twin BedsbrbrbrbrView: Gulf ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements (non refundable)br$125 + Application to Longbeach Condo Association,br$25 Check made payable to Lighthouse Property Management
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