Vacation Condo Rentals By Owner In Longboat Key, FL

$224.92

Partial Beach View 2 Bedroom Condo

Longboat Key, Florida, United States

Beautiful unit on the 3rd floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit.brbrCome stay a month or more!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-Fi and 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.brbrYou are just moments from St Armand's Circle with all its top shopping and dining options. Easy access to the areas arts and cultural activities and moments from Sarasota Airport.

2

Bed

2

Bath

4

Sleeps

$262.62

/ Nightly

Condo

Beachplace 3 - 302 by FGC

Longboat Key, Florida, United States

Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows and doors. This is a new and bright condo ready for your beach adventure. Condo is located in the Gated Beachplace complex with pre-set chairs and umbrellas on the beach and a very amenity rich environment.brThis unit has two parking spaces. One covered and one outside, brbrCome stay a month or more!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-Fi and 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.brbrYou are just moments from St Armand's Circle with all its top shopping and dining options. Easy access to the areas arts and cultural activities and moments from Sarasota Airport.

2

Bed

2

Bath

4

Sleeps

$401.91

/ Nightly

Condo

5 Steps to the Beach!!! Modern 1-bedroom condo in brilliant Longboat Key w/ pool

Longboat Key, Florida, United States

Newly renovated (November 2025) modern first-floor condo literally five steps away from the sand, walking outside from the lanai.brbrOne bedroom /One bath brKing bed in PrimarybrQueen sleeper sofa in the living roombrbrKey code entrance brFree parkingbrHeated Swimming pool on sitebrFree Beach loungers on the beach brPaid laundry machines on site brMid Island next to everything brWiFi, cable, free parkingbrUsually 7-night minimum brbrBring your toothbrush and bathing suite and prepare to unwind and relax!!!!

1

Bed

1

Bath

4

Sleeps

$230.37

/ Nightly

Villa

Beach Villa on Longboat Key

Longboat Key, Florida, United States

Your home away from home in Longboat Key with 2 bedrooms. This adorable villa features 1 king bed and 1 queen bed, perfect for a cozy stay. Convenient bathtub and shower in the 2 bathrooms. With AC to keep you cool, this charming retreat is ideal for guests looking for a relaxing getaway. We look forward to hosting you at our place.

2

Bed

2

Bath

4

Sleeps

$401.39

/ Nightly

Condo

Oceanfront Condo with panoramic Gulf Views, Pool, Hot Tub and Fitness Center

Longboat Key, Florida, United States

The Privateer – Gulf-Front Luxury with Panoramic Ocean Views and Resort-Style AmenitiesbrbrWelcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. Perched on the 10th floor, this stunning coastal retreat invites you to experience refined seaside living with unobstructed, panoramic views of the Gulf of Mexico. From the moment you enter, natural light fills the open interior, leading you to two private balconies that offer a front-row seat to mesmerizing sunsets, gentle sea breezes, and the soothing rhythm of waves along the shore.brbrThis fully furnished residence was designed for comfort, style, and relaxation — the perfect setting for a luxurious seasonal escape or extended coastal retreat. Every detail has been curated to blend modern elegance with the relaxed charm of the island, making it easy to settle in and feel right at home.brbrElegant InteriorsbrbrThe spacious floor plan offers a seamless flow between the living, dining, and kitchen areas, creating a serene environment for entertaining guests or enjoying quiet evenings by the Gulf.brThe well-appointed kitchen comes fully equipped with everything you need for home-cooked meals, while the comfortable bedrooms and thoughtfully selected furnishings reflect a refined coastal aesthetic. Each room captures stunning natural light and tranquil water views, ensuring that every moment indoors feels as inspiring as the view outside.brbrWorld-Class AmenitiesbrbrLife at The Privateer feels like a private resort experience. Guests enjoy access to an exceptional collection of amenities, including:brbrA heated beachfront pool and jacuzzi overlooking the GulfbrbrPrivate beach access with complimentary chairs and umbrellasbrbrA fully equipped fitness centerbrbrTennis courts and beautifully maintained groundsbrbrOutdoor grilling areas and shaded dining spacesbrbrElegant social and lounge areas perfect for gatherings or sunset cocktailsbrbrEvery day here offers the opportunity to unwind, rejuvenate, and embrace the effortless beauty of coastal living.brbrPrime Longboat Key LocationbrbrLocated on the southern end of Longboat Key, The Privateer combines the tranquility of a gated beachfront community with convenient access to the best the area has to offer. Explore the boutiques, fine dining, and art galleries of St. Armands Circle, or spend an afternoon discovering downtown Sarasota’s cultural attractions, just a short drive away. Whether you’re looking for quiet days on the sand or evenings out on the town, everything you need is within easy reach.brbrExperience Longboat Key LivingbrbrWake up to the sound of the ocean, spend your days soaking in the Florida sun, and unwind each evening with unforgettable Gulf-front sunsets. At The Privateer, every detail is designed to elevate your stay — offering luxury, comfort, and the timeless beauty of the Gulf of Mexico.brbrA 3D walkthrough is available for a closer look at this exceptional property.

2

Bed

2

Bath

4

Sleeps

$295.69

/ Nightly

Condo

Ground floor 2/2! Glass Lanai! Sleeps 5!

Longboat Key, Florida, United States

Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautiful 2/2 directly on the bay! Gorgeous views off the patio and from the master bedroom suite. Ground floor with front and back access! Pool is 30 feet away, so easy access yet still private! Relax at the condo or stroll to the Gulf side and enjoy the powder white sand on the beach! Close proximity traveling south to St. Armands circle, Mote marine and fabulous restaurants or travel north and visit Anna Maria Island!brbrbr• Carefree check-in, go straight to your unit no office visit required.br• Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker.br• Comfortable living room area w/ a large flat screen TV.br• Washer and Dryer Conveniently located in unit.br• Master bedroom including a KING size bed with brand new mattress , flat screen TV, walk in shower, walk in closet, and beautiful view of the bay!br• Spacious guest bedroom with a QUEEN BED. Lanai has a single size sleeper perfect for a small person. br• Large Patio overlooking the bay with outdoor seating and a table, pool access is just 30 feet away! brHarbor Villa Club amenitiesbr• Poolbr• Hot Tubbr• Tennis Courtbr• Boat Slips (Rented Separately)br• Covered Parkingbr• ElevatorsbrbrThe 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. Looking 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. 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.

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Sleeps

$299.44

/ Nightly

Condo

Longboat Key Beachfront Resort with Tennis by The Bay & Key Collection

Longboat Key, Florida, United States

Enjoy a newly remodeled beachside vacation rental condo featuring 3 bedrooms and 2 bathrooms, just steps from the sandy beach. Experience a vibrant community with amenities like pickleball and tennis courts, communal pools, and private beach access for the ultimate coastal getaway!brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you.brbrThe Bay and Key Collection offer a wide range of services including:br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you'll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Preferred Vendors' meaning you can trust the company you use for rentals.brbrAll properties listed with The Bay and Key Collection benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrWith its prime location in a private community, you'll enjoy peace and privacy during your stay, while still being just a short distance from local amenities with plenty of grocery stores, attractions, and beautiful beaches. Whether you're seeking relaxation, adventure, or a bit of both, this vacation rental is the perfect home base for your next getaway. brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you. brbrThe Bay and Key Collection offer a wide range of services including: br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations. br- 'Preferred Vendors' meaning you can trust the company you use for rentals.brbrAll properties listed with The Bay and Key Collection benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrExperience the coastal lifestyle this ground floor, end unit, 3 bedroom, 2 bathroom condo offers. It was completely remodeled in the fall of 2023, with all new floors, new appliances, bathrooms, and a new kitchen. Located in the beachfront resort-style Club Longboat Beach and Tennis Condominium, your vacation starts when you arrive and start enjoying the perks of maintenance-free living. 2 heated pools, one for adults only and one for younger children, a jacuzzi, a fitness center, and multiple tennis courts all only steps away from your back patio. Some Tennis courts were recently turned into Pickleball courts. The community plans Pickleball lessons from January 2024. brbrThe fully equipped kitchen, with new quartz countertops, offers an abundant amount of cabinetry suitable for storing all of your cooking needs. The expansive living room renders a remarkable amount of natural sunlight, offering the option to enjoy your meals at the breakfast bar or the separate dining area provided. Step out into the Florida room and enjoy the sun on cooler winter days, or open up the sliding doors to invite the outside. The two sizable bedrooms share a bathroom with walk-in a shower. The master bedroom, much like the living room, boasts natural sunlight streaming in from the sliding doors. The master bedroom has an ensuite bathroom with a double vanity and a new walking shower. In the mood for outdoor dining while admiring the beauty of painted skies provided by the daily sunsets The spacious back patio, allows you to enjoy life outside, especially with Florida's ideal year-round climate. The condo has 3 TVs, free high-speed internet access, and cable TV. Your beach chair awaits you at the Gulf’s aqua-blue water's edge on world-renowned Longboat Key, which is only minutes away from this condo. Sit back and take in the tranquility provided by the sound of the aqua-blue water crashing into the stunning sugar sand. Want to explore more things nearby This location is convenient for visiting other high-rated Florida beaches or enjoying shopping and dining in downtown Sarasota, and St. Armands Circle.brbrParking is available in a designated parking spot just steps away from the front door (to the left behind the wall). The spot is marked with the apartment's number 316. Additional parking for guests is available on the other side of the driveway. These spots are not designated and unmarked.brbrCity of Longboat Key RRR-00980.2023brbrOn I-75, exit 210 FL-780W/Fruitville Rd heading West. Follow signs to Lido Key and Longboat Key. Take the first exit on St. Armands Circle on Lido key heading North to Longboat Key. Once you have passed the bridge to Longboat Key, follow the Rd (Gul of Mexico Dr.) for 6.5 Miles. The Club Longboat will be on your left side. Pull into the property and turn right. Unit #316 will be towards the end of the building on your left.brbrPer City of Longboat Key's Rental Ordinance - This property must be rented for a minimum of 30 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.brbrThis property is not available for instant booking due to the HOA application that is required. Lead time for this can vary from 7 days to 30 days. Enquire to find out more information.

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Bath

Sleeps

$372.59

/ Nightly

Condo

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Longboat Key, Florida, United States

The Beach Resort is located on exclusive Long Boat key a 12-mile long barrier Island off the Florida peninsula coast. Here you will find a serene and relaxing place to unwind while enjoying meticulously maintained gardens, lawns with exotic palm trees, tropical plants and a wide variety of natures wildlife all surrounded by white sandy Beaches and pristine turquoise blue ocean. brYou can sit and relax outdoors on your private balcony and watch the dolphins swim just offshore and then at night have dinner a glass of fine wine and view spectacular sunsets!brYes, its no surprise visitors come to Longboat Key from all over the world to relax, unwind and rejuvenate themselves so WELCOME TO PARADISE!!brThe biggest problem you will have is forcing yourself to leave.brThis property has recently been remodeled and renovated with unique and custom built furniture and decor.brThe interior design features hand made artisan furniture and decor that shows industrial designed pieces combined with a rustic flair throughout.brIf you would like something a little different to the cookie cutter hotel chain rooms then this condo is for you.brMinimum 2 day rental.

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Sleeps

$257.27

/ Nightly

Condo

Beach place in Longboat Key.

Longboat Key, Florida, United States

Welcome to your dream getaway! Our beautifully appointed 2-bedroom, 2- bath condo offers the perfect balance of comfort, style, and breathtaking views. Located just steps away from the pristine sandy shores, this is the ultimate destination for relaxation and fun.brbrFor more photos and details visit: beachplacelongboatkey.net

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Bath

Sleeps

$369.96

/ Nightly

Condo

Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony

Longboat Key, Florida, United States

Beachfront Condo – No Street to Cross, Just Steps to the SandbrEnjoy panoramic Gulf and sunset views from your private covered balcony in this spacious 1-bedroom, 1-bath condo on the 4th floor of Turtle Crawl Inn. Located directly on the beach in beautiful Longboat Key, FL, this unit offers unobstructed 180° views from every room and the peaceful sound of the waves just outside your door.brbrInside the Condo:brNewly renovated bathroom and flooringbr55` 4K smart TV in the living room and 24` smart TV in the bedroombrTwo queen beds in the bedroombrFull sleeper sofa in the living roombrFully equipped kitchenbrComplimentary Wi-Fi, beach chairs, and parkingbrbrPlease note: Cancellations are subject to a 4% credit card transaction charge.brbrResort Amenities:brHeated poolbrElevatorbrLaundry roombrFree onsite parking with plenty of spacebrWell-maintained, five-story beachfront building with friendly on-site managementbrbrLocation:brLongboat Key is a barrier island off Florida’s Gulf Coast, offering a quiet and upscale setting just minutes from Sarasota and Bradenton.brApprox. 60 miles south of St. Petersburg and TampabrAbout 90 miles north of Fort Myers and Cape CoralbrEasy access to restaurants, shopping, golf, and Sarasota’s cultural attractionsbrbrPlease Note:brIn the event of a hurricane, severe weather, or unexpected power outage, the pool and resort amenities may be temporarily unavailable.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.

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Sleeps

$221.14

/ Nightly

Apartment

Experience a resort feel vacation on the beach in Longboat Key

Longboat Key, Florida, United States

Two bedrooms, two baths, (approximately 1500 square feet) with a study, two balconies, an assigned covered parking , located on the desirable Gulf side of Longboat Key, steps away from the beach with private, deeded access to the Gulf of Mexico. The unit is in an amenity-rich, carefully manicured community, with 750 feet of splendid Gulf frontage, two heated swimming pools (one adult and one family), a spa, a sauna, shuffleboard, clubhouse, with game room, library & kitchen, fitness center, and eight Har-Tru tennis courts (with an on-site tennis pro available for lessons). There is an elevator and also a grocery cart and a luggage cart close to the elevator to use. The unit has its own covered reserved parking and there is plenty of guest parking available. Beach chairs and umbrellas are provided by the complex and are already set up for you on the beach. Just grab a towel and walk to the beach!

2

Bed

2

Bath

6

Sleeps

$621.5

/ Nightly

Villa

Longboat Key home rental w/ PRIVATE Pool & 1 minute to private beach access!

Longboat Key, Florida, United States

Welcome to your dream rental home, perfectly positioned amid the Harbourside Course of the prestigious Longboat Key Club! This stunning 3BD/2.5BA villa has been fully renovated and is ready for your next vacation! Revel in breathtaking views of the lush golf course and the vibrant Florida sunsets that paint the sky each evening.brStep inside to discover:brbr1 minute to Private Beach: Rental property offers access to private exclusive Bay Isle Beach Club with access along the Gulf of Mexico. Bike accessible along with plenty of parking!brbrPrivate Pool: Sliding doors from the open family room lead you to this relaxing outdoor space, ideal for soaking up the sun or hosting lively get-togethers.brbr5 minute drive to world class restaurants and shopping: Spend the day or night walking beautiful St. Armands Circle, or lovely downtown Sarasota.brbrVaulted Ceilings & Skylights: Bask in an abundance of natural light and airy, open spaces.brbrSpacious Open Kitchen: A seamless blend of the Family Room and Kitchen, perfect for both intimate gatherings and grand entertaining.brbrPaved Drive & 2-Car Garage: Elegant and convenient!brbrThe master suite is your private retreat, featuring a terrace walk-out where you can enjoy tranquil views and fresh air. Situated in a secure community of Harbour Circle, this home is nestled behind the exclusive gates of Bay Isles. Take advantage of your own private pool or use community pool and deeded beach access through the Bay Isles Beach Club, where you can walk the white sandy beaches of LBK or enjoy beachside BBQs, picnics, and spirited games of beach volleyball.brbrThis renovated gem offers modern luxury and an unbeatable location—don't miss your chance to make it yours!brbr

3

Bed

2

Bath

6

Sleeps

$449.14

/ Nightly

Condo

OCEANFRONT STAY! PANORAMIC GULF VIEWS!

Longboat Key, Florida, United States

Ready to swap the hustle and bustle for sun-soaked shores and gentle ocean breezes Meet Sea N Blue, your ultimate vacation rental paradise! Nestled along the stunning coastline, our beautiful beachfront getaway is more than just a place to stay; it’s an experience that will rejuvenate your spirit and create memories to last a lifetime.brbr ️ Why Choose Sea N Blue brbr- Breathtaking Views: Wake up to panoramic ocean views that stretch as far as the eye can see. Enjoy your morning coffee on the balcony as the soothing sound of the waves surrounds you, and keep an eye out for playful dolphins. Savor meals outdoors, and wrap up your day by marveling at breathtaking sunsets.br br- Cozy Comfort: With spacious, elegantly designed interiors, Sea N Blue offers all the comforts of home. Enjoy modern amenities, a fully equipped kitchen, and new plush bedding for the perfect night’s sleep. Our spacious 1300 sq ft. southwest corner unit is climate-controlled and boasts a private beachfront balcony. The interior has been completely remodeled into a modern open-concept living area, featuring upscale finishes and elegant, comfortable furnishings.brbrThe bright and airy layout offers stunning views of the Gulf and the pristine white sand beach from nearly every room. The interior combines clean lines with a coastal-contemporary design, featuring a chef-inspired kitchen equipped with new appliances, a wine fridge, updated full bathrooms, and in-unit washer and dryer.brbrThe primary bedroom with ensuite bath features a King-size canopy bed with brand-new mattress and bedding. Wake up to breathtaking sunrise views over Sarasota Bay from the bayside window, while the gulf-side window offers views of the sparkling waters. The guest bedroom also showcases a gulf view and brand-new mattresses that can be arranged as either two Twin XL beds or one King-size bed according to your comfort and needs.brbrUnwind on the spacious private balcony on the outdoor loveseat/daybed, or relax in the living room on the large sectional sofa, complemented by a custom corner entertainment wall featuring a flat-screen Smart TV and a modern linear fireplace. Our condo is fully stocked with essentials, including bath and beach towels, kitchen appliances, utensils, bed linens, and more. To enhance your vacation, optional services such as grocery, beer or wine delivery from Publix on the island can be arranged. We strive to make your stay enjoyable and restful with amenities such as free parking, complimentary beach chairs and loungers, outdoor heated pool, grill, community room, and more.brbrLocated mid-key in the Longboat Beach House, a six-story, 22-unit building with elevator, our fourth-floor unit ensures a private beachfront experience just steps away from the water. Our rental is close to many wonderful restaurants, attractions and activities on Longboat Key, and provides easy access to Sarasota, St. Armands Circle, Lido Key, Bradenton, and Anna Maria Island. Whether you’re a thrill-seeker or a relaxation enthusiast, our prime location puts you just steps away from sandy beaches, water sports, and local attractions Enjoy a wide range of activities, from walking and biking to fishing, sightseeing, and shopping! Downtown Sarasota offers world-class entertainment, while nature enthusiasts can explore local parks and trails for birdwatching and outdoor adventures.brbrLongboat Key’s abundance of natural beauty and minimal commercialization, makes it a charming and ideal destination for your next getaway.. brbrBook your stay today and discover the magic of Sea N Blue! Whether it’s a romantic getaway, a family vacation, or a solo retreat, we’ve got everything you need to make your seaside dreams come true. brbr*Please note the minimum rental period is one month, for a maximum of four guests. brSorry, no pets and no smoking, per condo association regulations. brbr Click calendar to check availability and take the first step toward making Sea N Blue you’re Happy Place on Longboat Key!

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Sleeps

$327.11

/ Nightly

Condo

Longboat Key Escape–Resort Pool + Ocean: Beachplace Condo # 7-102 by RVA

Longboat Key, Florida, United States

Welcome to Beachplace 7-102, a nicely decorated two-bedroom, two-bath unit at Beachplace that includes direct, private walk-down access to the community pool and beach areas from your private patio. Accommodations include a spacious master bedroom complete with adjustable King-sized bed, a separate guest bedroom with twin beds and easy guest bathroom access. Enjoy the partial Gulf-front and pool views from your private patio overlooking the beautiful beaches of Longboat Key. Unit 7-102 includes comfortable furnishings, WIFI Internet access and more. Located in the popular, gated community of Beachplace - the condominium complex includes a large community pool and hot tub area, tennis courts, fitness center, private beach access and ample walking and biking trails. This spot is a favorite on the island, and for good reason, so book your next escape today. brbrbrbrAccommodations: Two-bedroom, two-bathroombrbrbrbrLocation: 1075 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrView: Ocean/Gulf ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $165 Fee + Application; $25 Cancellation Penalty

2

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2

Bath

4

Sleeps

$255.47

/ Nightly

Condo

Gulf-Front Escape- 2BR Beachfront Condo by RVA

Longboat Key, Florida, United States

Gulf-Front Escape — 2BR/2BA Condo on Longboat KeybrbrStep into beachfront bliss at this beautifully updated 2-bedroom, 2-bath condo in a quiet Gulf-front community on Longboat Key. Unit 102 offers direct access to powder-soft sand and stunning turquoise water—perfect for morning strolls, sun-soaked afternoons, and unforgettable sunsets right from your private balcony.brbrInside, you’ll find a bright, open living space with coastal décor and sliding glass doors that bring the outdoors in. The fully equipped kitchen features granite countertops and stainless-steel appliances, making meal prep easy and enjoyable.brbrThe spacious primary suite includes an en-suite bath, while the second bedroom and full guest bath provide comfortable accommodations for families or couples traveling together. Enjoy the convenience of in-unit laundry, complimentary Wi-Fi, and on-site parking.brbrRelax at the heated community pool, unwind on the beach, and enjoy Longboat Key’s peaceful, upscale atmosphere—all while being just a short drive to St. Armand’s Circle, dining, shops, and local attractions.brbrYour perfect Gulf-front getaway starts here.brBook now and make this beachfront paradise your home away from home!brbrAccommodations: Two-bedroom, two-bathroombrbrAmenities: Private Patio Overlooking The Gulf, Full-size Kitchen, Community Pool, Washer/Dryer, Direct Beach Access, Community Grill, Fitness CenterbrbrLocation: 4401 Gulf of Mexico Dr. #102, Longboat KeybrbrBedding: 1 King, 2 Queens, Sleep SofabrbrView: Gulf ViewsbrbrMinimum Night Requirements: 2 MonthsbrbrAssociation Requirements: $100 Fee

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Sleeps

$442.99

/ Nightly

Condo

Beach Condo with Quiet, Private Beach

Longboat Key, Florida, United States

Relax with your loved ones at this quiet, 2-bedroom beachfront condo at the Beach Castle Resort on Longboat Key. This second-floor corner unit is a perfect beach vacation rental for couples or families, offering a chance to recharge, reconnect, and make new memories.brbrWake up to stunning Gulf of Mexico views from the primary bedroom and your private patio—the perfect spot for a morning coffee or an evening drink while you take in the amazing sunsets and listen to the waves. The home is comfortably furnished to accommodate your group:brbr1. Primary Bedroom: A relaxing sanctuary with a king-sized bed, a 55-inch smart TV, and direct patio access with water views. Complete with an attached en-suite bathroom.brbr2. Second Bedroom: Features two full-sized beds and a 50-inch Roku smart TV and an attached en-suite bathroombrbr3. Living Room: Unwind with a movie on the 58-inch 4K Roku smart TV. The space also includes a queen-sized sleeper sofa for additional guests.brbrParking: One assigned on-site parking space is included with your stay. If needed, limited off-site parking for one additional vehicle may be available by advance request for $25 per day. Please note that on-site parking is restricted to your assigned space only, and vehicles parked in unassigned spots may be subject to towing.brbrKey Amenities:br--Fully equipped kitchen with a blender for frozen drinks.br--Free in-building washer and dryer.br--High-speed fiber Wi-Fi and a dedicated workspace.br--Children`s books and toys to keep younger guests entertained.brbrThe secluded hideaway resort is wonderfully maintained and incredibly quiet and peaceful. The beaches on Longboat Key are just a few miles north of Siesta Key, consistently rated the top beach in the country. With the same water and sands as Siesta Key, Longboat Key is much less crowded, truly feeling like your own private slice of paradise. One of our absolute favorite things to do while here is sitting out on the beach after dark and stargazing! This quiet retreat offers a great escape from it all -- a chance to recharge your batteries, reconnect with loved ones and make new memories.brbrYour unit is wonderfully located on the northern part of Longboat Key, a very short walk to great restaurants, cafés and an ice cream shop. Bicycle rentals are also available to further explore everything the island has to offer. St Armands Circle is less than 9 miles to the south and is an exciting hub of waterfront locations, fine dining and shopping.brbrGuests will enjoy complete privacy and access to the entire condo via a smart lock. Your unique access code will be provided in your confirmation email and will activate at check-in.brbrAs our guest, you`ll have access to the full range of amenities at the unique Beach Castle Resort, which extends from the Gulf of Mexico to Sarasota Bay:brbr* Private Beach Access: Enjoy private beach access just steps from your door.br* Beach Gear: Complimentary beach chairs and umbrellas are provided for your use.br* Pool & Hot Tub: Take a dip in the heated community pool or unwind in the hot tub.br* Bay Access: Launch a kayak from the newly constructed pier on the bay or enjoy some great fishing. Two fishing poles are available for your use in the unit.brbr**Traveling with Children:** brWe provide a Pack `N Play with a mattress, a booster seat and bed rails. You just need to supply the sheets for the mattressbrbr**Liability Waiver:** brOur property offers wonderful opportunities for swimming, fishing, and enjoying the beach, dock, and pool. By agreeing to the House Rules, you acknowledge the inherent risks involved and accept full responsibility for any bodily injury. Children must be supervised at all times near water, as there are no lifeguards on duty. Diving from the dock is not allowed.brbr**Cancellation Policy:** brPlease be aware that our cancellation policy is firm. Environmental factors beyond our control (such as hurricanes or red tide) will not be grounds for a refund. We strongly recommend purchasing trip insurance. For additional flexibility, you may want to explore ‘Cancel for Any Reason’ (CFAR) coverage.brbrPlease Note: We provide a starter kit of essentials (soap, paper towels, toilet paper). As this is a self-service resort without daily housekeeping, guests are responsible for purchasing additional supplies for their stay. A Publix grocery store is conveniently located nearby.

2

Bed

2

Bath

6

Sleeps

$989.38

/ Nightly

Condo

Stunning 3 bedroom Gulf View Condo! Paradise awaits you!

Longboat Key, Florida, United States

Welcome to your luxurious Gulf-front retreat at En Provence! This stunning 3-bedroom, 3.5-bathroom condo offers 3400 square feet of Florida living at its finest. Enjoy breathtaking views of the Gulf of Mexico from your spacious wrap-around terrace, complete with a built-in gas grill for outdoor entertaining. Step inside to discover a gourmet kitchen with state-of-the-art appliances, granite counter tops, and a family gathering area. The open floor plan flows seamlessly into the living and dining areas, all with floor-to-ceiling windows overlooking the beach. With private terraces off each bedroom, marble floors, 10-foot ceilings, and a private elevator opening directly into your home, every detail exudes luxury. Plus, indulge in the convenience of a private enclosed two-car garage. Outside, lush tropical foliage surrounds the Gulf side pool and spa, offering the perfect setting for relaxation and enjoyment. Just minutes away, you'll find award-winning restaurants, shopping destinations like St Armands Circle, and recreational activities at The Longboat Key Club.brbrExperience the epitome of Gulf Coast living at En Provence. With access to communal pool & hot tub. Gated Community with access to a beautiful clubhouse. Book your stay today! brbrProperty requires 90 night minimum for all stays.brbrAll Guest and pet (dog) must be approved by the board. brbr

3

Bed

3

Bath

6

Sleeps

$339.54

/ Nightly

Condo

Beachfront Elegance-Gulf Views & Sunsets at Castillian #111N Condo by RVA

Longboat Key, Florida, United States

RVA offers Gulf front living in this two-bedroom, two-bath condominium on Longboat Key. Enjoy your private lanai, or take a walk on the pristine beaches.The Castillian community offers secure and enjoyable living with under-building parking, a heated community pool and hot tub, tennis courts, and secure access. Located on quiet Longboat Key, these units are just minutes away from St. Armand's Circle and downtown Sarasota where you will find unique dining, upscale shopping and lively entertainment. Available for monthly rental. brbrbrbrAccommodations: Two-bedroom, two-bathbrbrbrbrAmenities: Private Patio, Elevator, Community Hot Tub, Full-size Kitchen, Community Pool, Wireless Internet, Access, Tennis Courts, Washer/Dryer, GrillbrbrbrbrLocation: 4545 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Requirements: 1 monthbrbrbrbrAssociation Requirements: $100 Fee + Application; 30-Day Approval Time

2

Bed

2

Bath

4

Sleeps

$282.08

/ Nightly

Condo

Beachview 2/2 condo on Longboat Key

Longboat Key, Florida, United States

Welcome to your Sunset Beach Retro Retreat by FVC, a fun, funky 2-bedroom, 2-bath condo on beautiful Longboat Key where coastal relaxation meets a splash of 80’s flair!brbrStep inside and you’ll immediately feel the personality, this is not your typical neutral beach rental. With bold colors, playful décor, and nostalgic touches throughout, this condo delivers a unique, feel-good vibe while still offering all the comfort you need for a perfect getaway.brbrThe spacious layout includes a primary bedroom with a king bed for ultimate comfort and a guest bedroom with a queen bed, making it ideal for couples, families, or a friends’ escape. Two full bathrooms provide plenty of space for everyone to get ready with ease.brbrOne of the standout features is the large private patio, offering beautiful views of the pool, beach, and the Gulf, the perfect spot for morning coffee or sunset cocktails. Even better, you’ll enjoy direct walk-down access, making it incredibly easy to go from your patio to the pool deck or straight onto the sand in just moments.brbrJust steps from the shoreline, you can spend your days soaking up the sun, strolling for seashells, or unwinding to the sound of the waves. And when evening rolls around, you’ll have a front-row seat to Longboat Key’s famous Gulf Coast sunsets, truly unforgettable.brbrBack inside, enjoy a light and bright living space full of retro charm, along with a fully equipped kitchen perfect for everything from casual meals to entertaining.brbrIf you’re looking for a stay that’s relaxed, memorable, and full of character, this is it.brProfessionally managed by Florida Vacation Connection, ensuring a seamless, high-quality experience from booking to checkout.brbrCome experience a little retro magic by the beach, your Longboat Key escape awaits.

Bed

Bath

Sleeps

$311.51

/ Nightly

Condo

Long Boat Key Vacation Home

Longboat Key, Florida, United States

This is a two bedroom, two bathroom open layout condo with an ally kitchen and views of both the gulf and the bay. The condo is equipped with a full kitchen, washer and dryer and two balconies. The building has a private beach, pool and tennis/ pickle ball court.

2

Bed

2

Bath

3

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Vacation Condo Rentals By Owner In Longboat Key, FL

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