Home Vacation Condo Rentals By Owner In Longboat Key, FL

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$346.08

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Find Your Sunshine Sanctuary on Longboat Key

Longboat Key, Florida, United States

Welcome to your sunshine-soaked escape on Crane’s Bay—where every condo gives you room to breathe, stretch, and settle into full vacation mode. With spacious layouts of 1,600 sq. ft. or more, these two-bedroom, two-bath retreats are designed for families, friend groups, and anyone craving a little extra elbow room.brbrYour Home Base in ParadisebrMain Bedroom: King bed + private bath = your personal recharge zonebrSecond Bedroom: Two twins bedsbrLiving Room: Sleeper sofa for the extra tagalongsbrFully Equipped Kitchen: Full-size appliances, cookware, blender (hello, smoothies), toaster, teapot, and coffeepot—because vacation fuel mattersbrIn-Unit Washer/Dryer: Stackable, convenient, and ready for sandy swimsuitsbrbrResort Perks Worth Packing ForbrHeated Outdoor Pool + Whirlpool (Dawn to Dusk)brRelax, float, soak—repeat. Winter who brTennis & Pickleball CourtsbrPlay a friendly match or unleash your inner Serena—your call.brGear on DeckbrAsk at check-in about our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing poles.br(First come, first vacationed.)brbrLobby Fun ZonebrBooks, games, and videos for rainy days, quiet nights, or the kid who always needs “one more thing to do.”brPicnic + BBQ AreabrGrill up something delicious under the Florida sky.brbrGood-to-Know DetailsbrParking: No campers, motorhomes, or trailers. Call us for storage options.brSmoking: Allowed only on balconies and designated spots—not inside.brPets: We love them, but not here. No pets permitted.brMax Occupancy: Six guests total (yep, kids count).brHouse Rules: No parties, no pets, no smoking/vaping inside.brViews: Balcony views vary by unitbrbrAge Requirement: 21+ to rent and check in.brMaintenance: Things happen—our team works quickly to make it right.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM
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Exceptional(36)

$352.82

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Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access

Longboat Key, Florida, United States

Looking for a winter glow-up Welcome to Longboat Key—where sandy beaches, soft breezes, and that “I could really get used to this” island vibe turn even the coldest months into sunshine season. Your home base: a spacious 1600+ sq. ft. 2BR condo perched right over Crane’s Bay with front-row seats to postcard-perfect views (and the occasional surprise manatee cameo).brbrInside, you’ll find all the comforts of home—only sunnier.brMain Bedroom: King bed + private bath with a jetted tub worthy of vacation-level bubble bathsbrGuest Room: Two twin beds (aka the cozy kid zone or bestie bunk room)brLiving Room: Sleeper sofa for extra guestsbrSecond Bathroom: Easy access for everyone—no vacation “line for the shower” chaosbrbrA Kitchen Built for Vacation ModebrFully equipped with full-size appliances, roomy countertops, a breakfast nook made for slow mornings, and all the essentials—dishes, pots, pans, toaster, coffee pot, and utensils.brPlus, in-unit washer + dryer to keep swimsuits fresh and sandy footprints in check.brbrResort Perks to Keep the Good Times RollingbrHeated Outdoor Pool & Whirlpool (Dawn to Dusk)brPerfect for cold-weather refugees and sunset soakers.brTennis & Pickleball CourtsbrServe up some friendly competition—or just look sporty, no judgment.brBeach + Gear AccessbrAsk at check-in for our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing equipment.br(First come, first sun-kissed.)brPicnic & BBQ AreabrGrill, chill, and dine under the Florida sky.brLobby EntertainmentbrBooks, games, and videos—because even paradise has cozy indoor days.brbrBefore You Book, A Few Helpful NotesbrbrParking: No campers, motorhomes, or trailers. (We’ve got storage options—call us.)brSmoking: Allowed only on balconies or designated areas. Not inside.brPets: We love them too, but this property is pet-free.brOccupancy: Max of 6 guests, kiddos included.brHouse Rules: No pets, no smoking/vaping inside, no parties.brViews: your view may vary.brAge Requirement: 21+ to rent and check in.brMaintenance: If anything pops up, our team is quick on the fix.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM
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2-Bedroom Beachfront Condo on Private Beach Longboat Key

Longboat Key, Florida, United States

Available for long-term rental, this 2-bedroom, 2-bath beachfront condo is located on a private beach in Longboat Key, ideally situated between Anna Maria Island and Sarasota. The community offers resort-style amenities while maintaining a peaceful coastal setting.brbrThe primary bedroom features a queen-sized bed. The guest bedroom includes a bunk bed with a full-size bed on the bottom, a twin on top, and a twin trundle.brbrThe unit includes air conditioning, an in-unit washer and dryer, and an open patio for enjoying ocean breezes. Residents have access to a community pool, on-site workout room, and beach chairs provided on the private beach. This well-maintained condo provides comfortable beachfront living for an extended stay.
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Exceptional(1)

$194.53

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Charming 2-bedroom fully renovated condo on Longboat Key with bay/ocean views.

Longboat Key, Florida, United States

Make yourself at home in this terrific 2-bedroom Longboat Key retreat. Fully renovated in 2025 with a king bed, queen bed, and full bed, this condo is perfect for a relaxing getaway. Enjoy the soothing ambiance of the space, complete with modern amenities like WiFi, AC, and washer/dryer. The 2 bathrooms are equipped with a hair dryer, iron shampoo and linens for your convenience. brbrEnjoy our private beach access just 100 yards from the front door. The pool comes heated and kept at a nice 85 degrees year round. Enjoy our kayaks for exercise or fishing. Speaking of exercise, our complex offers a full tennis court.brbrFor your dining experience, we are 5 miles from Armands Circle. If you like French cuisine, you will enjoy Maison Blanc a Michelin star restaurant just across the road. brbrBook now and enjoy everything this condo has to offer.
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Exceptional(1)

$467.75

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Charming 2 BR Longboat Key condo with ocean view - Flirty Flamingo

Longboat Key, Florida, United States

Located in the highly sought-after Beachplace on Longboat Key and professionally managed by Gulf Coast Vacation Rentals, this beautiful 2 bedroom, 2 bath condo is located on the top floor in Building 3 and is absolutely stunning! With a pleasant view from the balcony, you can relax with your morning coffee listening to the waves or enjoy a glass of wine and toast to the spectacular sunset. The master bedroom features a king-size bed, ensuite bath, flat-screen TV, and a lovely view. The spare bedroom offers twin accommodation, flat-screen TV, and access to the guest bath. This unit has been outfitted with all the comforts of home including cable TV and Wi-Fi.brbrAmenities at BeachPlace include a large Olympic size heated lap pool, a whirlpool spa, a clubhouse with a fitness center and wireless internet, 4 tennis courts, and miles of white sand beach. Looking for restaurants, shopping, and the arts... St Armand's Circle is just a five-minute drive and downtown Sarasota is less than 15 minutes away.brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties. No pets per HOA. Beach furniture is for the exclusive use of Beachplace residents/guests and their accompanied guests, and may not be used to store extra towels, beach bags, or other material. Tennis hours are 8 am to 10 p.m. Lights go out automatically at 10 p.m., so please plan accordingly. Tennis courts are for the exclusive use of Beachplace residents and their invited guests. Reservations/registration is required during the October to May season. Players may reserve one court per unit through the pool attendant, up to 24 hours in advance. A picnic area with a gas grill is available next to the pool area and tennis courts for residents and their guests. The grill may be used between the hours of 12:00 Noon and 10:00 p.m. Users are responsible for cleaning the grill and disposing of all trash. Pets of any kind are not permitted on Beachplace property. The only exception is guide dogs which are protected under the Americans with Disabilities Act. All Day guest's names and planned arrivals must be called into Security to inform the guards so their entrance can be assured.brbrYour reservation may require you to fill out a Home Owners Association application that may request personal details. Any application fees required by the HOA are non-refundable.
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Exceptional(18)

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Newly Remodeled! Directly Across from Beach ~ Condo

Longboat Key, Florida, United States

The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. The island has very little commercialization and there are no fast food chain, but yet still has all the conveniences wanted. brbrNo crowds, only a peaceful and relaxing beach that will feel as if it is your piece of heaven. This is a ground floor condo with one bedroom, one bath and ample parking. brbrThe condo contains a full kitchen, king bed, bath/shower, washer/dryer (coin operated), wood deck with dining table. We have a pack and play for the kids. We do not provide an air mattress for the unit, but you are welcome to bring one. We also do not have a sleeper sofa. brbrWe request no more than 4 people staying in the unit. Beach chairs and linens are provided. Enjoy watching a Live TV or Netflix on a 55 inch and 42 inch LCD TVs.brbrKeywords: condominium, one bedroom, great value. brbr
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Exceptional(61)

$475.54

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Gulf Front 1 BR with Great Room Awesome View End Unit 227 with 42' TV

Longboat Key, Florida, United States

Spend some time in paradise! Relax in a comfortable Laz Boy Recliner overlooking the Gulf. Enjoy breakfast while watching the dolphins play. Come see picturesque sunsets that seem surreal. Newly remodeled beach front two story condo offers an awesome full gulf view with private terrace. This one bedroom, KING size bed(amazing mattress), one bath condo, has a fully equipped kitchen (cherry wood cabinets, granite countertops, stainless steel appliances)2 flat screen TV's (1 TV in Bedroom & 1 in Living room 42') with DVD. There is also an extremely comfortable Murphy bed (queen size) in a cherry wood cabinetry along with a pull out sofa. brbr For convenience a washer/dryer is located in your condo. Free Wireless Internet, Beautiful heated pool equipped with comfortable lounge chairs, umbrella and Weber grill all offering the full gulf view for you to enjoy. A wonderful place to sit back, relax and enjoy the natural beauty of Longboat Key.br
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Exceptional(16)

$290.04

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Luxurious Beachfront Villa with Private Pool

Longboat Key, Florida, United States

This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secluded beach, heated community pool, private balconies, community hot tub and secure access. The unit is recently renovated and located across the street from a public park, a convenience store, two restaurants and a bicycle shop. The Villas of Avignon is an eight-unit complex is less than ten miles from shopping, dining, and entertainment of St. Armand's Circle and less than 15 miles from downtown Sarasota.
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$143.12

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BEACHFRONT VACATION RENTAL WITH FULL GULF VIEWS!

Longboat Key, Florida, United States

Spectacular Gulf views of the beach and sunsets from this updated and spacious 5th floor 2-bedroom, 2-bath turnkey furnished condo at The Arbormar, located mid-island on Longboat Key and close to restuarants and shoppiing. Open balcony looks directly onto the beach with water views from living and dining room. Flat screen smart cable TV and FREE WiFi Internet access in living room and bedrooms. Pull-out couch in living room. Fully equipped and spacious kitchen with plenty of cabinet and storage space. Master bedroom has king bed with master bath en-suite and walk-in shower, and built-in closet storage space. Guest bedroom has twin beds and guest bath is tub/shower. Shared coin-operated washer/dryer (only 4 units/floor) immediately outside unit. This unit is fully furnished - - just bring food and clothes!brbrArbormar offers many fine amenities including assigned covered parking, heated swimming pool, golf putting green beach-side and shuffleboard with picnic area, BBQ grill and kayak storage. The 1st floor clubroom offers catering kitchen and spacious seating for parties and groups. There is a fitness center overlooking the Gulf, sauna with shower and restrooms directly off the pool. Enjoy spectacular Gulf views in this tropical paradise setting on Longboat Key.brbrContact Wagner Realty for pricing and availablity *****brbrAmenities Include:brbr- View: Full Gulfbrbr- Application Fee Req.: $100brbr- Waterfront: Yesbrbr- Beach Distance: on the beachbrbr- Pool, Heated: heated poolbrbr- Beach Access: deededbrbr- Pool: communitybrbr- TV Cable/Satellite: cable TVbrbr- Internet Access: WiFi Internet accessbrbr- washer dryer: Sharedbrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: Twinsbrbr- Beds Pull-out: Pull out couchbrbr- Elevator: Yesbrbr- Balcony: Balconybrbr- TVs/VCR/DVD: Flat screen TVsbrbr- Furnished: Turnkeybrbr- Master Bath Features: En-suitebrbr- Walk-In Shower: Yesbrbr- Garage: Carportbrbr- Activities: Pool-fitness-saunabrbr- Minimum Stay: 30 nightsbrbr- Agent: Gregory Kossbrbr- Office: Longboat Key
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Home Most popular vacation rentals in Longboat Key

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$884.08

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Private vacation home

Hidden Bay/Beach Paradise

Longboat Key, Florida, United States

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$746.18

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Canal Front Home - 8 min walk to beach. RRR-00953.2023

Longboat Key, Florida, United States

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$747.69

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Longboat Key home on the canal and a 5 minute walk to the beach

Longboat Key, Florida, United States

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$755.36

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LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach along the turquoise Gulf of Mexico.

Longboat Key, Florida, United States

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$767.89

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Beachfront 4th floor 4BR Longboat Key Condo With Stunning Gulf Views Paradise Sur Mer

Longboat Key, Florida, United States

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$861.14

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3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!

Longboat Key, Florida, United States

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$1148.84

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Beach Front Condo on Gulf of Mexico

Longboat Key, Florida, United States

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$2112.85

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Luxury Beachfront Living - St Regis Waterfront Residency - Longboat Key - Sunset Reflections

Longboat Key, Florida, United States

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$1196.70

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Renovated Beachfront 2 Bedroom Condo by FVC

Longboat Key, Florida, United States

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$739.37

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Stunning gulf front 6th floor Longboat Key Condo with endless views - Once Upon A Tide

Longboat Key, Florida, United States

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