Vacation Rentals in Longboat Key, Sarasota FL

Welcome to Harbour Villa #305 – a beautifully updated bayfront retreat offering the perfect blend of comfort, style, and island elegance. Recently renovated, this spacious condominium features a fully stocked gourmet kitchen with brand-new appliances, sleek countertops, and every essential for effortless dining at home. Entertain with ease at the built-in wet bar, complete with a plug-in ice maker, coffee maker, insulated cooler, wine and cocktail glassware, and beach towels, everything you need for a carefree stay. The inviting living area is designed for relaxation, complete with a plus.......

5.0 Star Review

• Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker. • Comfortable living room with bay views • Washer and Dryer Conveniently located in unit. • Master bedroom with a king size bed, flat screen TV, walk in shower, walk in closet, and beautiful view of the bay! • Spacious guest bedroom with king size bed • Large Patio overlooking the bay with outdoor seating with corner unit views and serenity Harbor Villa Club amenities • Pool • Hot Tub â€.......

5.0 Star Review

Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views off the patio and from the master bedroom suite. 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! • Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker. • Comfortable living roo.......

5.0 Star Review

Come enjoy some peace in quiet in beautiful Longboat Key. This 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! We hope you have the opportunity to enjoy some of the unique features of this beautiful unit: • Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker. • Dining Room Table that’s seats four. • Bright and cozy living room area w/ a l.......

4.7 Star Review

Upscale, bright, southern exposure two in-suites condo with beautiful views of the Sarasota Bay was fully remodeled by Leader/Sawa Design Studio and was intended for owner’s personal use. This third-floor corner unit called the Captain’s quarters is the largest model in the complex (1550 sq ft) offers cathedral ceilings, the privacy of two in-suites, large private patio away from the pool noise, open concept modern kitchen, spacious dining and living rooms which makes it ideal if you look for privacy, space and quietness. Condo Main Features: - Large marble dining room table that sea.......

5.0 Star Review

Welcome to The Tree House in Cedars East Longboat Key! ⚓Short bike ride to beaches ⚓Community Pool, Kayak Launch, Nature Trails, Fishing & More ⚓Less than 1 mile to Joan Community Park ⚓Fully stocked kitchen for all of your favorite home cooked meals ⚓High speed Wi-Fi included Smart lock for Self-Check-in 2 Bedroom Townhome Sleeps 6 Welcome to the "Tree House!" This recently renovated, and freshly furnished property is located in the beautiful community of Cedars East Tennis Resort. The Tree House is nestled between protected mangroves and the Sarasota Bay. It is locat.......

4.7 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Longboat Key Vacation Rental

Pet Friendly - Pets Allowed

100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in. Experience 24/7 Live Customer Service Private Beach Access Heated Pool What's Included: -Full access to all amenities. -Bikes. -Tennis courts. -Tennis rackets. -Jr. size Olympic pool. -Workout facility open 24/7. -Restaurant. -Tiki Bar. -Proshop. -Fishing Pier. -Boardwalks. A Bayside tennis and residential community in the heart of Longboat Key, FL. Sunshine and warm breezes accent the well-appointed tri-level townhouses that surround Cedars Tennis Resort & Club. Some of our residen.......

4.2 Star Review

2 Bedrooms - 2.5 Baths - Sleeps 6
Longboat Key Vacation Rental

Pet Friendly - Pets Allowed

Beautiful beachfront unit on the 5th floor with amazing beach and sunset views. 2 bedroom, 2 bath unit with many modern upgrades. Master bedroom has a king bed and second bedroom has two twins. The master bath is a walk-in shower. Second bathroom is tub/shower combo. Come make this your home for a month or more. 30 day rental required. It is located in Beachplace, which is a premier gated community on South Longboat. There is ample closet space throughout, with a washer/dryer in-unit. The condo has high speed wireless internet and cable TV, water and electric included in price. Has new windows.......

0.0 Star Review

2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico. Beautifully appointed kitchen and living areas complement the modern features of the condo. You will feel right at home staying at the Pierre. Beachfront Paradise nestled in a private gated community. The Pierre is beautifully maintained and the Condo has every feature accounted for. Pierre.......

0.0 Star Review

Live life on the beach---Private parking included! Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Gulf-front views, this sophisticated and chic 4th floor condo with balcony has it all! This condo has modern updates throughout including upgraded kitchen and bathrooms and hardwood flooring in living and dining areas. The Large master bedroom has a King bed, an en-suite bathroom with a walk-in shower and dual sinks with a separate seating area. The guest bedroom has two twin beds and an adjoining full bathroom with tub and shower. Both Bed.......

5.0 Star Review

Beautiful beachfront unit on the 5th floor of building 8. 2 bedroom, 2 bath unit with stunning views and very well appointing furnishings. This unit is in high demand. RRR-00586.2023 On the soft white sand beaches of Longboat Key, Beach Place offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility........

0.0 Star Review

This home located in the sought after Seaplace community has a very personal feel to it and has a balcony with a side view that highlights the Gulf of Mexico. This unit is perfect for a person or couple that wants to enjoy the beach and pool and stay in a friendly community. Master bedroom is spacious with connected master bath. This condo is located on the 4th floor has an amazing view of the Gulf and Beach. Seaplace is a gulf-front community that sits on 42 acres. Enjoy a half mile of beachfront and 1-mile walking trail in addition to two heated pools and three Har-Tru tennis courts........

0.0 Star Review

Sought after beachfront unit on the 5th floor of building 9 and an end unit. 2 bedroom, 2 bath unit with stunning views and very well appointing furnishings. Beachplace is one of Longboat Key's premier vacation rental locations on the island! Amazing Gulf Views and private parking. This condo has new furnishings. Master has a king bed and 2nd bedroom has a king bed. Both Bedrooms and Living room have Tv's. There is ample closet space throughout, with a washer/dryer in-unit. The condo has HDTV and wireless internet in every room. The well-maintained and gorgeous grounds include the following am.......

0.0 Star Review

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. This unit has two parking spaces. One covered and one outside, Come stay a month or more! The.......

0.0 Star Review

Beautiful Beachplace beachfront unit on the 3rd floor spectacular Gulf and beach view. Has brand new windows and doors and is an end unit in building 3 with glass sliding doors on 2 walls of the living room. This is the closest building to the pool. It has 2 parking spaces. One is covered. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades and a very open feel. The views are amazing. Washer/Dryer in unit. Max 4 persons allowed for rentals at Beachplace in a 2 bedroom condo. RRR-00595.2023 On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and .......

0.0 Star Review

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. On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility........

0.0 Star Review

** Welcome to our beachfront Longboat Key condo! If you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos of Beachplace 8-204 and see for yourself. By the way, the unit is located on thirty-one beautifully landscaped acres on the second floor of Building 8 at Beachplace. The condo’s second floor location feels intimate to the gulf and beach. And the pool and lush grounds provide added attractions. T.......

5.0 Star Review

Beautiful beachfront unit on the 2nd floor with lake view and partial Gulf. This is a beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. It just feels like home. Beachplace is a gated condominium with a variety of amenities including a long stretch encompassing 1,450 linear feet of the soft white sand beach. Chairs and Umbrellas are available for use. It also has a large pool , fitness center and 3 tennis courts. Town requirements are a 30 day rental and rentals are on a calendar month basis. Off-season may allow mid-month to mid-month. Washer/Dryer in unit. Two parking sp.......

0.0 Star Review

Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs and umbrellas included • Wi-Fi • Lighted tennis courts • Heated pool and hot tub • Two state of the art fitness centers • Air conditioned clubhouse • BBQ gas grills by the pool. New windows/doors installed in condo ( not yet in pictures).. On the soft white sand beaches of .......

0.0 Star Review

Beautiful beachfront unit on the 5th floor with lake view and partial Gulf. Beautifully appointed 3 bedroom, 2 bath unit with a real feel of home. King Bed in Master, Queen Bed in 2nd Bedroom and 2 twins in 3rd bedroom. RRR-00586.2023 On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility........

5.0 Star Review

Beautiful beachfront walk-out unit on the 1st floor with amazing direct beach and sunset views. 2 bedroom, 2 bath unit with many modern upgrades including well appointed Kitchen which opens into the Dining and living area. Crown molding, raised ceiling, gorgeous floors, well appointed master bathroom and many additional features. Built in desk in 2nd bedroom. HDTV and Wireless internet in every room. 1 exterior Parking Space included The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs and umbrellas .......

0.0 Star Review

Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and Gulf of Mexico to the right and the Bay and downtown to the left. Look no further as this is paradise. Master bedroom has a King bed and second bedroom enjoys a Queen bed and a Single bed. This unit also has brand new windows and doors throughout. You will feel at home here. One month minimum rent.......

5.0 Star Review

Available Starting September for 3 or more months. Available in season Raffia & grass cloth wallpaper, textured bath tiles, pebble shower flooring, reed shades and plantation shutters and paneled solid wood doors. Tumbled travertine stone interior floors and balconies blends perfectly. An updated eat-in kitchen with a wall of windows shows off the greige cabinets, granite counters, stainless steel appliances, designer light fixtures, Mackenzie Childs hardware and open pantry. The master suite enjoys gulf views, separate walk-in closets, built in desk, and updated bath is a true retreat. In add.......

0.0 Star Review

Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very rare find. Building Balcony work is occuring Jan and Feb 2025 Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Oceanfront views, this top floor unit boasts a double balcony. This condo has it all including 2 bedrooms each with a King bed. It is freshly renovated and ready to be your home-away-from-home for a month or more. The Large master bedroom has a King bed, master bathroom with a walk-in shower and dual sinks. The gue.......

5.0 Star Review

Beautiful fully remodeled condo in Beachplace. Raised ceilings, tile floors, upgraded kitchen including a wine fridge, upgraded finishes throughout. This unit books quickly so contact us today for your vacation home in paradise. The open bright kitchen has cerulean glass tile backsplash that warms the white custom cabinetry, quartz marble countertops, upgraded stainless steel appliances, and wine refrigerator. The large farm sink adds rich character and utility while entertaining your guests on the sculptured quartz open peninsula. An adjacent café bar is perfectly situated for your small a.......

0.0 Star Review

Come enjoy the Beach - Private parking included. Beautiful beachfront unit on the 3rd floor with a Beach and Lake view. Beachplace Building 3 unit 304. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. A beautiful unit with shiplap wall in living room and master bedroom, great flooring throughout, beautiful walk in shower and a view that will keep you on the balcony full time. This one is very well remodeled and ready for immediate renters. Beachplace is one of Longboat Key's premier vacation rental locations on the island! There is ample closet space throughout, with a w.......

0.0 Star Review

Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This is a great condo for you to call home for a month or more. Condo is meticulously clean and well cared for. Owners have upgraded the furnishings including large smart TV's One month Minimum. The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate.. New listing. Come to the Beach. Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Ameni.......

0.0 Star Review

Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse condo located on the 15th floor of Islands West Complex. You will love the beach views and fast Wi-Fi. Master bedroom with King bed has amazing views of the Bay and the Sarasota Downtown Skyline . The second bedroom has a double bed and twin trundle and enjoys the same wonderful view. . Islands West is the ideal location on Longboat as it is located towards the Southern end of the island at the intersection of the Publix Shopping Center on the Gulf Side. Very convenient to shops.......

0.0 Star Review

Beautiful beachfront unit on the 2nd floor with lake view and partial Gulf. This is a beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. It just feels like home. It was decorated by Anne Folsom Smith. It has many custom features, including hand crafted furniture, unique kitchen backsplash and sliding stainless doors covering W/D. Completely renovated, with tile floors throughout, high ceilings with upgraded light fixtures, hurricane resistant floor-to-ceiling windows and modernized bathrooms. Kitchen boasts sleek cabinetry, custom granite countertops, high end appliances a.......

0.0 Star Review

New Listing! Perfect beach view elevated walkdown level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is the best of the best at Beachplace. Beachplace is Longboat Key's premier vacation rental location on the island! With amazing direct Oceanfront views, this walkdown unit is highly desirable. This condo has it all including 2 bedrooms. Imagine sitting on the balcony taking in the spectacular sunsets Longboat has to offer. It is gorgeously renovated and ready to be your home-away-from-home for a month or more. The large master bedroom has a King be.......

0.0 Star Review

3 Bedroom and 3 Bath condo located in the resort community of Beachplace Association. Faces the golf course and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. End unit with lots of light in the living space with 2 sets of sliding doors. The master suite offers lush views and access to the balcony. Bathroom offers a dressing area with 2 sinks and large closet. Master bath has a walk-in shower. The kitchen offers a breakfast bar, laundry closet (washer/dryer) and full appliances. Being and end unit, th.......

5.0 Star Review

Escape to Your Beachfront Oasis Awaits! Imagine waking up to the sparkling turquoise waters of the Gulf just steps away from your walk-down balcony. This beautifully appointed 2-bedroom, 2-bathroom condo, on the raised first floor of Beachplace Building 3, offers panoramic views of both the gulf and the sparkling pool below. Beachplace is Longboat Key's premier vacation rental location for a reason! This condo boasts modern upgrades and ample closet space throughout, with the convenience of a washer and dryer in-unit. Unwind and reconnect with loved ones in the spacious living area, equipped w.......

0.0 Star Review

New Listing! Ultra-Luxury level expertly renovated 2 bedroom condo offers modern elegance. Thoughtful updating includes raised ceilings, tumbled marble flooring, quartz counters, impact windows, recessed lighting, linear AC vents for a sleek modern look, solid interior doors and so much more. The primary suite pampers owners with a King Size bed, big water views, large walk-in closet, modern carpeting, dual vanity with under cabinet lighting, luxurious frosted glass enclosed shower space and upgraded door access to the terrace. 2nd bedroom has a queen bed and twin bunk beds. Maximum 4 people f.......

0.0 Star Review

Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. The sunsets are breathtaking. You will love the beach views and fast Wi-Fi. This is a luxury rental. Condo has a single unit washer/dryer in one. There is a Islands West is the ideal location on Longboat as it is located towards the Southern end of the island at the intersection of the Publix Shopping Center on the Gulf Side. Very convenient to shops and dining and just a short drive to St. Armand's Circle or Downtown Sarasota. Enjoy the Gulf front pool and spa, clubhouse, fi.......

0.0 Star Review

Beautiful unit on the 5th floor with lake/pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs and umbrellas included • Wi-Fi • Lighted tennis courts • Heated pool and hot tub • Two state of the art fitness centers • Air conditioned clubhouse • BBQ gas grills by the pool. On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres a.......

0.0 Star Review

Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool Gulf breeze as you witness the nightly spectacle of a fiery sunset. Inside, immerse yourself in a world of coastal contemporary elegance. Every detail, from the designer furnishings to the artistic touches, has been meticulously curated to create a luxurious retreat. The gourmet kitchen, featurin.......

5.0 Star Review

Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible panorama! This luxurious condo offers a king-size master bedroom with stunning bay and skyline views, and a comfortable second bedroom with a queen bed. The open-concept kitchen, living, and dining area seamlessly flow together, all bathed in natural light from expansive Gulf-facing windows. Prepare meals while enjoying the ever-changing seascape, then gather around the table to share stories of your day. Islands West boasts the ideal Longboat location. Situated towards the s.......

0.0 Star Review

2 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course with limited Gulf view and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. All NEW furnishings throughout this pristine condo with large tv in living room. The master suite with a king bed offers lush views and access to the balcony as well as a very large tv. Bathroom offers a dressing area with 2 sinks and large closet. Master bath has a very modern walk-in shower. The kitchen offers a breakfa.......

5.0 Star Review

Updated top-floor 2 Bedroom + Den with a pullout sleeper with stunning water views from nearly every room. Enjoy the private beach just steps away, featuring 750’ of Gulf frontage and renowned sugary white sand. The open concept layout is perfect for coastal vacationing, complemented by two spacious balconies offering prime seats for breathtaking Gulf sunsets. Experience Coastal Elegance at Club Longboat 332 Discover the ultimate beachfront retreat at Club Longboat 332, a top-floor condo offering breathtaking water views from bedrooms and living room. This modern 2-bedroom, plus den with .......

5.0 Star Review

This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity that comes along seldom. This impressive home is your rental opportunity to live your best life and indulge in the finer things. As you step inside, prepare to be awestruck by the stunning views of the Gulf of Mexico that greet you. The kitchen and appliances recently receiving a modern and sophisticated makeover, as well as new flooring in the kitchen and living room. The owners suite is your personal oasis, a place where you can unwind and rejuvenate. With its breathtaking .......

0.0 Star Review

Experience Coastal Elegance at Beachplace Penthouse Welcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking panoramic views of the pristine beach, the shimmering Gulf of Mexico, and mesmerizing sunsets that paint the sky year-round. Step onto the expansive wrap-around balcony and let the gentle sea breeze and stunning vistas captivate your senses. Floor-to-ceiling sliding glass doors seamlessly conn.......

0.0 Star Review

This home located in the sought after Seaplace community has a very personal feel to it and the beach is steps away from the building. Stunning 2-story, 2-bedroom/2.5 bath “townhouse-layout” condominium on the 2nd floor in SEAPLACE, one of Longboat Key's most desirable and beautiful communities. Located steps from the beach in the highly sought-after direct Gulf-front G1 building, this bright, contemporary, and spacious home was beautifully renovated in 2019 for easy, sophisticated living. Designer furnished, it features a light filled great room, coveted powder room on the lower lev.......

0.0 Star Review

Welcome to this stunning 2-bedroom, 2-bath residence on Longboat Key. - Expansive water views from the living room, master bedroom, and screened lanai - Turnkey furnished with modern décor and a custom kitchen pantry - Both bedrooms feature luxurious King-sized beds - Private beach access just minutes away - Four heated swimming pools and tennis courts - Daily wildlife visits from manatees and dolphins Experience stunning water views from this 2-bedroom, 2-bath Longboat Key retreat, perfect for 4 guests. The open living area, master bedroom, and enclosed lanai all offer panoramic views of t.......

5.0 Star Review

Escape to paradise at this spacious 2-story beachfront retreat on Longboat Key! - 2 bedrooms, 2 bathrooms, sleeps 6 - Stunning Gulf views and private beach access - Fully equipped kitchen and open-plan living room - Heated community pool and hot tub - 2-car garage for convenience - Minutes from dining, shopping, and Sarasota’s charm Experience comfort, space, and relaxation all in one place. Welcome to Your Luxury Beachfront Retreat on Longboat Key! Escape to paradise at this spacious 2-story beachfront retreat on Longboat Key! With 2 bedrooms and 2 bathrooms, it sleeps up to 6 guests. En.......

5.0 Star Review

Fully renovated 1BR/1BA 2nd-floor condo at Beach Castle Resort, Longboat Key. Bright, airy interiors, stylish furnishings, steps from Sarasota Bay and Gulf of Mexico. Perfect beach escape for relaxation or adventure. Escape to paradise at Beach Castle Resort #18, a bayside jewel on exclusive Longboat Key, Florida. Nestled between Sarasota Bay and the Gulf of Mexico, this updated 1-bed, 1-bath condo offers stunning tropical garden views and private beach access. Awake to bay vistas, enjoy coffee on the private lanai amid ocean breezes. Features new furnishings, king bed, modern appliances, and .......

0.0 Star Review