34228, Florida, United States Vacation Rental Homes By Owner - Page 29

$303.45

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.

Bed

Bath

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.

Bed

Bath

Sleeps

$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

Bath

4

Sleeps

$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!)

Bed

Bath

Sleeps

$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.

Bed

Bath

Sleeps

$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.

Bed

Bath

Sleeps

$534.66

/ Nightly

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.

3

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.

1

Bed

1

Bath

4

Sleeps

$282.5

/ Nightly

Condo

Gulf & Greenbelt Views, No-Expense-Spared Remodel, Seaplace Oasis

Longboat Key, Florida, United States

Escape to paradise in this completely remodeled, no-expense-spared 2nd floor end-unit condo with no unit above at the gated Seaplace beachfront community on Longboat Key. This oversized 1-bedroom, 1.5-bath gem (1,094 sq ft + 112 sq ft screened lanai) offers partial gulf views and greenbelt setting from the expansive lanai—perfect for sipping wine while watching spectacular sunsets. Just 178 yards from the pristine white-sand beach, the convenient second-floor location gives you quick access to the shore from the nearby elevator or stairs adjacent to the condo. Relax on your private screened-in lanai with high-quality Polywood furniture and a WiFi-enabled ceiling fan, all protected by custom 95% UV-blocking solar shades. The redesigned layout features a gourmet open-concept kitchen with soft-close cabinetry, Cambria Quartz counters, GE Café appliance suite (convection oven, warming drawer, induction cooktop), and a fully-stocked kitchen to make your extended stay feel like home. The coastal vibe interiors include porcelain plank driftwood tile floors, Cypress pecky wood and shiplap accent walls, smooth plastered ceilings and custom LED recessed lighting. Fully updated bathrooms with Carrara marble counters, elegant tile accents and double-vanity in the primary bath off the bedroom on the second level. There are smart flat screen TVs in the living room and bedroom to enjoy all of your favorite streaming and an LG stacked washer/dryer on the first level. Enjoy resort-style living across 42 manicured acres with two heated lap swimming pools, spas, a fitness center, three tennis courts, one mile of scenic trails, barbecue areas, and clubhouse with barbecue grills. Seaplace offers 24/7 guarded gate security and you're just one complex north of the iconic St. Regis. This turnkey coastal retreat delivers luxury, comfort, and unforgettable Gulf Coast memories. Book now for your slice of Longboat Key paradise! AVAILABLE NOV. & DEC. 2026 - BOTH MONTHS $7,500 PER MONTH. OR.. EITHER NOV. OR DEC. FOR THE MONTH: $8,000. ALSO AVAILABLE JAN. 2027-MAY 2027 WITH A 3-MONTH MINIMUM AT $7,000 PER MONTH. Please inquire with owner on preferred dates.

1

Bed

1

Bath

2

Sleeps

$183.27

/ Nightly

Condo

Fairway Bay #155 by FVC

Longboat Key, Florida, United States

Fairway Bay Fifth-Floor Retreat: Unparalleled Sarasota Bay Views brOffered by Florida Vacation Connections brbrExperience the epitome of coastal living in this exquisite two-bedroom, two-bathroom residence, perfectly perched on the fifth floor of Fairway Bay, a sought-after, amenity-rich community on Longboat Key. Spanning 1,442+/- sq. ft., this recently renovated condo showcases breathtaking panoramic views of Sarasota Bay, manicured grounds, serene waterways with mangroves, and the vibrant city skyline beyond. A private elevator leads to this stunning retreat, where natural light and refined design details create an ambiance of luxury and tranquility. brbrLiving and Entertaining Spaces brUpon entering the foyer, you’ll be greeted by a bright, open-concept living space thoughtfully designed for comfort and elegance. New waterproof flooring flows seamlessly throughout, complementing coastal-inspired tones and furnishings. The spacious living room is furnished with all-new furniture, linens, and two smart TVs, ensuring relaxation and modern convenience. A computer desk, complete with an on-site HP wireless printer, caters to your work-from-home needs. brbrThe kitchen, open to the dining and living areas, is both stylish and functional. With ample cabinetry, a large pantry, and brand-new countertop appliances, cookware, and cutlery, it’s perfect for both casual meals and entertaining guests. brbrBedrooms and Guest Accommodations br- Primary Suite: The primary bedroom offers direct access to the oversized terrace, where you can wake up to the serene beauty of Sarasota Bay. Highlights include wood floors, a walk-in closet, a new ceiling fan, and a spa-inspired en-suite bathroom with dual vanities, a separate water closet, and a walk-in shower featuring a frameless glass door, safety grab bars, and a new showerhead. br- Guest Suite: The guest bedroom provides comfort and privacy, complete with twin beds, an oversized closet, a ceiling fan, and an en-suite bathroom with a tub/shower combination and new fixtures. brbrThis residence comfortably accommodates up to six guests, making it ideal for family vacations or extended stays. brbrOutdoor LivingbrThe expansive terrace is the true showstopper of this residence, offering a peaceful oasis for relaxing or entertaining against the stunning backdrop of tropical landscaping and Sarasota Bay. Furnished for comfort, it’s the perfect spot to savor morning coffee, sunset cocktails, or al fresco dining. brbrFairway Bay Amenities brFairway Bay residents enjoy a host of exclusive amenities, including: br- Private, gated beach access and beach club. br- 24-hour gated security for peace of mind. br- Scenic walking trails through lush landscapes. br- Resort-style pools, hot tubs, and exercise facilities. br- Tennis and pickleball courts for active recreation. brbrLocated just a short walk from the luxurious new St. Regis Resort and a quick drive to St. Armands Circle, this residence is ideally positioned for enjoying world-class dining, shopping, and entertainment. Optional memberships at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are also available. brbrThis fifth-floor Fairway Bay residence is a rare find—move-in ready with all-new furnishings, just waiting for you to bring your suitcase. Don’t miss the chance to experience Longboat Key’s unparalleled charm and luxury. brbrOffered exclusively by Florida Vacation Connections.

2

Bed

2

Bath

4

Sleeps

$405.39

/ Nightly

Apartment

Sunset and beach view from your balcony Unit 501

Longboat Key, Florida, United States

Unit 501 is a stunning corner condo offering unobstructed views of the Gulf of Mexico and extra space thanks to its desirable corner layout. Enjoy sweeping, direct Gulf views along with additional natural light from the side window, creating a bright and airy coastal retreat.brbrThis one-bedroom, one-bath residence is located on the 5th floor and features an extra-large private balcony — the perfect place to relax, listen to the gentle sound of the waves, and watch some of the most breathtaking sunsets on Longboat Key. Located in the Tower and overlooking the Gulf, the condo is bright, spacious, and thoughtfully designed for comfort.brbrThe bedroom offers two queen beds, while the living room includes a convenient queen sofa bed, comfortably accommodating up to six guests. The generous living area provides plenty of room to unwind after a day on the beach.brbrPlease note: Cancellations are subject to a 4% credit card transaction charge.brbrThe condo also includes a fully equipped kitchen, dining area, cable TV, and Wi-Fi. Large sliding glass doors open to the balcony, allowing you to enjoy spectacular Gulf views from the comfort of the living space.brbrWith elevator access, you are just steps away from the heated pool, pristine beach, and community amenities. Our friendly on-site office staff is always available to assist and help make your stay enjoyable.brbrWhether you’re looking for peaceful beachside relaxation or easy access to nearby dining and nightlife, this is one of the best one-bedroom condos on Longboat Key — offering comfort, location, and excellent value.brTravel Insurance Recommendation:brWe strongly recommend purchasing travel insurance to protect against unexpected disruptions, including medical emergencies, flight cancellations, severe weather, and other unforeseen events. For a small daily cost, travel insurance offers peace of mind and financial security.

1

Bed

1

Bath

4

Sleeps

$286.55

/ Nightly

Private Vacation Home

Country Club Shores 4brm pool home by FVC

Longboat Key, Florida, United States

Soaring Spirits – A Newly Renovated Coastal Escape brProudly offered by FL Vacation Connection brbrStep inside this beautifully newly renovated, single-story coastal retreat, and you’ll instantly understand how it earned the name Soaring Spirits. Designed to be both calming and invigorating, the home’s coastal-chic décor features soothing hues that invite relaxation, while vibrant pops of color add a lively, uplifting energy. brbrIndulge in the ultimate indoor-outdoor lifestyle with an expansive covered patio, now enhanced with a motorized screen enclosure—allowing you to enjoy the fresh air with the touch of a button! Whether you're savoring an alfresco meal, gathering for a family game night, or unwinding with a good book, this inviting space is perfect for every occasion. brbrA Kitchen with a View brThe European-style kitchen is a dream for any home chef. With a smart, streamlined layout that makes meal prep a breeze and a window that frames stunning views of the sparkling pool and serene canal, cooking here is nothing short of a pleasure. brbrPoolside Perfection & Waterfront Bliss brThe sun-drenched pool beckons for a refreshing swim, while the surrounding deck offers plenty of lounge chairs for soaking up the Florida sunshine. Prefer the shade Retreat to the covered patio, where you can sip a chilled drink while embracing the gentle coastal breeze. brbrTake a leisurely stroll to the private dock, where you might catch a glimpse of a gentle Manatee swimming by. Feeling lucky Try your hand at fishing and see if you can reel in dinner! brbrRest & Recharge in Style brWhen the day winds down, retreat to one of the inviting bedrooms, each designed for comfort and tranquility. Sink into plush bedding, close your eyes, and drift into a restful sleep—tomorrow is another day to let your spirit soar! brbrImportant Notes:br- Renters do not have access to the boat, boat lift, or electrical box on the dock. br- No trailers or boat trailers of any kind are permitted on the premises. brbrTown of Longboat Key RRR.00188.2025

4

Bed

3

Bath

7

Sleeps

$394.64

/ Nightly

Cottage

2 bedroom 2 bath. Peaceful, Sunsets, White sands !! On the Gulf

Longboat Key, Florida, United States

Located in Longboat Key, enjoy what this 2-bedroom cottage has to offer. The welcoming space features a king bed and a twin bed, plus a cozy living room with a sofa bed for extra guests. Sleeps 5-6 people . Two bathrooms include refreshing showers and handy hair dryers. Stay comfortable year-round with air conditioning and heating throughout the cottage. Whether you’re relaxing indoors or planning your day, this perfect spot invites you to unwind and recharge from the walking distance to the beach and your nightlife restaurants from the Shore and Whitney‘s. We think our place will help you experience everything Longboat Key has to offer. For short or long vacations snowbirds welcome. 5 minutes walking distance to the beach.

2

Bed

2

Bath

5

Sleeps

$423.75

/ Nightly

Condo

Renovated Beach Penthouse sleeps 10 - luxurious Longboat Key Beach Florida!

Longboat Key, Florida, United States

One week Penthouse on beach of Longboat sleeps up to 10! Jan 9th to the 23rd availibility! Veranda Longboat Key Beach Resort!Two story penthouse suite off the Gulf of Mexico, sleeps ten, 4 full baths and 4 bedrooms. Private entry from either floor. Includes amenities: pool, jacuzzi, sauna, sailboats, kayaks, cabanas, bikes, indoor racquetball, fitness center, tennis & basketball courts, outdoor grills, and staff to help you find what you need and security to keep you safe. Award-winning restaurants and beaches in Longboat Key, nearby St Armand’s Circle, and downtown Sarasota and Siesta Key. Close to Sarasota/Bradenton International Airport.

Bed

Bath

Sleeps

$755.36

/ Nightly

Apartment

LaPlaya 205D January 2025 Discount!

Longboat Key, Florida, United States

Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute of the sunset. The unit has a fully equipped kitchen plus washer and dryer. All linens and beach towels are provided. Welcome to our island-style living.brbrThis spacious unit is bright and breezy with new décor and totally renovated kitchen and baths featuring sparkling granite and tile. The open floor plan provides sweeping views of the beach and gulf from the kitchen to the living and dining area, and on to the private porch and steps leading to the beach. All bedrooms are carpeted. The master bedroom on the 2nd level has floor-to-ceiling windows, and sliders to a sundeck overlooking the beach.brbr Soft shades of aquamarine provide a quiet color scheme for relaxing while enjoying the spectacular views of the beach and Gulf. Listen to the waves, or enjoy exquisite sunsets from the spacious balcony off the third level master bedroom, or from the screened lanai off the living/dining area on the second level.

Bed

Bath

Sleeps

$569

/ Nightly

Condo

Updated Beachfront Condo at Prestigious Long Boat Key Resort

Longboat Key, Florida, United States

Welcome to Suite Serenity, a beautiful beachfront King suite at the amazing Longboat Key Club resort. brbr Property Highlights:br✨ Heated resort-style poolbr✨ Elevatorbr✨ Beach chairs and umbrellabr✨ Beach and pool towelsbr✨ Private balconybr✨ Outdoor showerbr✨ Washer/dryer in unitbr✨ Free on-site parkingbr✨ Directly on the beachbrbrEnjoy a peaceful stay at one of the top resorts in the state of Florida. Take a dip in the resort style pool, and then walk to the beach and enjoy the warm waters of the Gulf of Mexico. In the evening, take in beautiful sunsets from your private balcony overlooking Lido Key. brbrThis spacious apartment is located on the second floor, beachfront in building 1. From the balcony you can see dolphins swim past and sunsets over the Gulf of Mexico. A dream vacation on a luxury getaway island that offers lazy beach days but also a large variety of golf courses and tennis courts, as well as top restaurants. brbrThe unit has wireless Internet access, a full-size kitchen, cable TV, complimentary parking, a large private balcony, and is located in a gated community and right at the beach. It is the perfect escape. brbr**PLEASE NOTE that use of the Golf/Tennis courts, hotel bars and restaurants, as well as other Country Club resort privileges are NOT included.** However, the use of the pool, whirlpool, and beach area is allowed. Guests are able to utilize beach chair, umbrella, and cabana rentals at their expense through the resort on the beach**brbrPAYMENT AND CANCELLATION TERMS WHEN BOOKING ON VRBObrbrAt the time of booking your credit card will be charged by Shore Thing Property Services LLC for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrWe require 25% deposit with the final payment due 60 days prior to your arrival date. Full payment will be due immediately if the arrival date is within 60 days.brbrAlthough the VRBO policy states no refunds, we will refund in the event that you need to cancel your reservation prior to 60 days before your arrival date. We will implement our Shore Thing Properties cancellation policy as indicated on the rental agreement. This allows for a refund of the deposit paid minus a $250 cancellation fee and the original management fee. Within 60 days of arrival there are no refunds.brbrADDITIONAL INFORMATION:brbrHouse keeping will provide you with a starter supply of toilet paper, soap, and garbage bags, but guests will likely need to replenish the supply during their stay.

1

Bed

1

Bath

4

Sleeps

$321.88

/ Nightly

Condo

2 Bedroom Beachfront Condo by FVC

Longboat Key, Florida, United States

Welcome to Players Club 402, a beautifully renovated 2-bedroom, 2-bathroom beachfront condominium located on the pristine shores of Longboat Key. Offered by Florida Vacation Connection, this stunning residence combines modern comfort, coastal style, and breathtaking Gulf views for the perfect island retreat.brbrStep inside to find a freshly updated interior with new furnishings throughout, creating a bright and relaxing space designed for effortless coastal living. The open living and dining area is filled with natural light and flows seamlessly onto the large private balcony, where you can enjoy incredible views overlooking the resort-style pool and the sparkling waters of the Gulf of Mexico. It’s the perfect setting for morning coffee, sunset cocktails, or simply taking in the beauty of Longboat Key.brbrThe primary suite features a comfortable king-size bed, ample closet space, and a beautifully updated en-suite bathroom. The guest bedroom offers two full beds, making it ideal for family or visiting guests, with convenient access to the second fully renovated bathroom.brbrThe fully equipped kitchen provides everything needed to prepare meals at home, and for added convenience the condo also includes an in-unit washer and dryer, allowing you to enjoy a longer stay with all the comforts of home.brbrPlayers Club is one of Longboat Key’s premier beachfront communities, offering direct private beach access, a heated beachfront pool and spa, fitness center, clubhouse, tennis and pickleball courts and beautifully maintained tropical grounds.brbrWhether you're enjoying the expansive balcony views, walking miles of white sand beach, or relaxing by the pool, Players Club 402 offers the perfect luxury island escape.brbrExperience the beauty and tranquility of Longboat Key, where every stay truly feels like coming home.brbrProfessionally managed by Florida Vacation Connection.

2

Bed

2

Bath

4

Sleeps

$350.93

/ Nightly

Condo

Waterfront, Spa/Pool, Private Paradise on Longboat Key!

Longboat Key, Florida, United States

Welcome to Paradise at the Harbour Villa Club #114! Enjoy the Captains Quarters end unit which boasts over 1500 sf of living space. A lovely 2/2 to nicely sleep 4 persons. All your living is conveniently on one floor, with open den next to kitchen. Spa and large pool just a short walk outside the lanai and just a few feet from the bay. 15 min walk to a private & gorgeous Beach! Spectacular bay views from every room. Enjoy onsite Tennis and grilling by the pool You will love it here!brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrThe spacebrCome enjoy some peace & quiet in beautiful Longboat Key!brbrThis clean and comfortable 2 bedroom, 2 bathroom condo on Sarasota Bay is perfect for a relaxing getaway. You can have the perfect vacation without even leaving this condo complex!brbrWe hope you have the opportunity to enjoy some of the unique features of this beautiful unit:brbr• Carefree check-in, go straight to your unit no office visit required.br• Fully-loaded Kitchen including microwave, stove, dishwasher, fridge, and coffee maker and even a wet bar.br• Dining Room Table that’s seats six.br• Bright and cozy living room area w/ large flat screen TV.br• Washer and Dryer Conveniently located inside unit.br• Master bedroom with a king-sized bed, walk-in shower, and peaceful view of the garden area.br• Spacious guest bedroom with Queen bed and private walk-in shower.br• Large Patio overlooking the bay with outdoor seating and a table.brbrHarbor Villa Club amenitiesbr• Heated Poolbr• Hot Tubbr• Tennis Courtbr• Covered ParkingbrbrSurrounding AreabrThe Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for.brbrLooking to go for a hike Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets at St. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.brbrOther things to notebr- Phenomenal Longboat Key location - Only minutes to Beaches, Restaurants and other local favoritesbr- HOA Application required-No Fee (Furnished after reservation made)br- This property has a minimum primary renter age requirement of 25.br- No Pets allowed per HOA. No exceptions.br- Upon booking, a signed rental agreement and government-issued photo identification are required prior to receiving an electronic access code to the property.br-Stays in excess of three weeks may incur an additional cleaning fee.

Bed

Bath

Sleeps

$315.27

/ Nightly

Private Vacation Home

Peaceful Longboat Key Canal Home

Longboat Key, Florida, United States

Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat docking. We're located on a quiet street in close proximity to Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserve.brbrRelax on your waterfront patio, perfect for outside dining, barbecues and quiet evenings. Bike, Kayak and Paddleboard rentals are available nearby to explore the island and waters. Beach wagon, chairs and umbrella included for your easy 0.5 mile walk to the beach. brbr30 Night Minimum

2

Bed

1

Bath

4

Sleeps

34228, Florida, United States Vacation Rental Homes By Owner - Page 29

$303.45

$258.42

$108.96

$273.98

$435.05

$174.21

$351.67

$534.66

$274.53

$282.5

$183.27

$405.39

$286.55

$394.64

$423.75

$755.36

$569

$321.88

$350.93

$315.27

Rent a place that suits your needs

Most popular vacation rentals in Longboat Key

$747.69

$2112.85

$1196.70

$1148.84

$1024.99

$884.08

$861.14

$767.89

$755.36

$670.46

Most Popular Cities in Florida