Vacation Rentals By Owner In Longboat Key, FL

brPlease DO NOT try to book this property initially as there is an approval process including a background check which can take about a week. Simply Ask Owner A Question first, then once approved we can go to the Request to Book stage. brbrTake advantage of the beach at your back door and enjoy this stunning vacation condominium with spectacular views of the Gulf of Mexico, located on Longboat Key- an extraordinary 11 mile barrier island along the coast of Sarasota, Florida. brbrOur beautiful 7th floor condo has two spacious bedrooms and two bathrooms in the highly sought after Islander Club and provides you with full Gulf views from every room! The outdoor patio is the length of the entire condominium and ideal for enjoying outdoor dining, warm Gulf breezes and the most unforgettable sunsets. From the 85 foot balcony, enjoy panoramic views that include downtown Sarasota all the way to Siesta Key.brbrThe living room combines with the dining area to provide an expansive open living space, including a pull out sofa for guests. Fall asleep listening to the mesmerizing sound of the surf from the spacious master suite which includes a king sized bed, large walk-in closet and private bath. The spacious and bright guest bedroom offers one queen and one twin bed, plenty of closet space and stunning beach and water views.brbrSituated on the south end of the Key, the Islander Club is just steps from the water's edge. Location, location, location! 4 miles from St. Armand's Circle, directly across from the Long Boat Key Club Golf Course and walking distance to the new Publix and CVS. During the day, utilize private beach access to swim in the Gulf or to fish off the pier. You can also enjoy lounging on the grand waterfront patio which offers a beautiful swimming pool. Your stay includes access to spectacular amenities at the Islander Club including an Olympic-sized heated pool, sauna, Har Tru tennis courts, library, billiard room, recreation room, Gulf front fitness room, secured lobby and on-site management.brbrThis barrier island is filled with beaches, boating, water sports, tennis, and two championship golf courses located at the Longboat Key Club. The Islander is conveniently near St. Armand's Circle and downtown Sarasota where you will find an abundance of upscale shops, fine dining and attractions, including museums, art galleries, entertainment and cultural activities.brbrThis island paradise could provide the perfect setting for your tranquil beach vacation year after year.brbrSTRICTLY No Smoking ANYWHERE in the Islander Property. No pets allowed in the building.brbr90 Day Minimum brbrSubject to Owner/HOA Board Approval. Rental subject to minimum lease requirements.brbrhttps://my.matterport.com/models/FCtcagccoZF cta_origin=last_created_space&organization=q16XknXHLAZ

Float Above The Waves In Paradise - Beach Front, 2 Bed, 2 Bath

Longboat Key, Florida, United States

Bed

Bath

4

Sleeps

Select Dates for Price

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, fitness center and on-premise tennis courts. Make your reservation today and start relaxing on the tranquil Beach that Longboat Key is so desired for. Take leisurely walks along the beach and enjoy the natural setting. brbrThis is a 3 month rental. Come and enjoy your time on Longboat Key. No pets allowed. Requires association application and approval. brRecently refurnished condo. Balcony furniture will be in place for time of rental. brbrYou will love this property.brKing bed in Primary bedroom

Gorgeous Beachside Condo in superior Longboat Location

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$333.42

Our building is located on the beach, this unit has an ISLAND view.br br Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.br br Please note: We do not allow Sunday or holiday arrivals and require a 7 night minimum stay.br br Welcome to the Longboat Key Sarasota's most enjoyable vacation spot ever.br If you are ready to relax and enjoy life, our rental apartment is waiting for you.br br Up to 4 person private accommodation in our 1 Bedroom / 1 Bath unit.br br Faces the sunrise over the island that you could enjoy every morning having a cup of coffee at a spacious private balcony off the living room. There is also an espresso machine for your use.br br Condo located right on the beach and provide complimentary WiFi, beach chairs and parking. Beachcomber condo has heated pool, 2 elevators and laundry room.br br Enjoy a peaceful night's sleep on a new luxurious king size bed.br br Prepare a full meal in your renovated fully equipped kitchen.br br Watch your favorite television shows, movies, sport and more with an 55'' flat panel HDTV.br br Relax on the 'Tommy Bahama' queen size sofa sleeper in the Living room. br br Full bath consisting of a tub/shower, vanity with sink and a toilet.br br Connect with family and friends using the free wireless internet access.br br The building has 2 elevators and laundry room.br br Directly on the Beach on mid Longboat Key.br br Across the street from a shopping plaza with a Publix Grocery Store, CVS Pharmacy, and a variety of smaller shops. br br Gulf side heated pool with lounge chairs and umbrella tables.br br Covered beachside sitting area, spacious sun deck and fabulous sunsets.br br Private white sand beach.br br Free Parking.br br Complimentary lounge chairs and barbeque grill.br br You will have easy access to public tennis courts and a marina.br br *This is a non-smoking unit.br br On behalf of our guests and owners that suffer from asthma and allergies, no pets are allowed on the property. No exceptions! $300 fine.br Amenities Include:br - Balcony: Yesbr - Bed Size 1st/Master: Kingbr - Beds Pull-out: Queenbr - Internet Access: Yesbr - Micro/Dishwash/Disp.: Yesbr - Refrig And Ice Maker: Yesbr - Square Footage, Est.: approx. 800 sq. feetbr - TV Cable/Satellite: Cablebr - TVs/VCR/DVD: 2/0/1br - View: Islandbr - washer dryer: on propertybr - Max number of People: 4br - Hair dryer: Yesbr - Bathtub/Shower: Yesbr - Beach front building: Yes

Beachcomber unit 401

Longboat Key, Florida, United States

Bed

Bath

4

Sleeps

$885.06

Summary:brWelcome to the picture-perfect, social media dream that is Villa Sereno by LUXVP. brThis 5-bedroom, 4.5 bathroom canal-front home is elegantly decorated and thoughtfully curated to include everything needed for a relaxing Florida retreat. The owner has thought of every detail from the comfortable furnishings to the personal device outlets by each bed, and everything in between to ensure every guest of Villa Sereno has the vacation of a lifetime. When you enter the home you step into the spacious living room area with vaulted ceilings and open concept viewing. Your formal dining room to the left is large enough to seat a crowd with ample space. The kitchen area is just off the dining room with every kitchen amenity one could possibly need. A family room is located off the kitchen with a comfortable couch -- the kind you can melt into for a relaxing evening. Off the back of the kitchen is the laundry room and a half bathroom. Traveling back through the kitchen and breakfast dining area your eyes immediately take in the breathtaking pool and canal-front views. Off the kitchen is a set of stairs leading up to a private guest bedroom with bathroom en-suite and a private balcony overlooking the front of the property. Back through the living room to the right is a fully-stocked office complete with printer capabilities, a desk and everything needed for a home office space. The next door includes the guest-accessible non-usable single-car garage (located on the west end of the property) but this garage is no ordinary garage. It comes stocked with bicycles and kayak supplies for the athletic members of your group. Still traveling down the hallway is another guest bedroom with en-suite bathroom, a separate full-size bathroom and a third guest bedroom with direct pool access and views. Traveling up the beautiful main staircase includes a game room with ample activities and TV watching with water views that might distract you from anything electronic. To the front of the house is another guest bedroom with bunk beds and supplies that make it the perfect spot for traveling kids. Another half bathroom is off the main hallway, with the master bedroom located upstairs to the back of the house. As you would expect, the master bedroom spares nothing in its pursuit of being amazing including a spacious layout, walk-in closet with ample storage plus an en-suite bathroom with a Jacuzzi tub and walk-in shower. The best feature of the master bedroom may be the private, open air patio located off the back of the house with canal, distant bay and pool views. We guarantee this will be a spot you retreat to unwind and relax. The outdoor pool is just as luxurious as the inside - including a full-size kitchen, large TV and plenty of seating. A private dock is available for fishing and viewing use along with 2 kayaks, paddles and life vests are provided. The boat lift is not available for guest use. Stop dreaming of your perfect vacation and start packing -- Villa Sereno is calling. Answer the phone!brAccommodations: 5-Bedroom, 5.5-BathroombrLocation: 524 Outrigger Lane, Longboat KeybrAmenities: High End Decor, On the Canal with Bay Access, Full-Size Kitchen with Wine Cooler, Office with Printer and Phone, Several En-Suite Bedrooms, Several Private Patios, Open-Air Pool with Removable Safety Gate, Hot Tub, Outdoor Kitchen, Grill, Outdoor TV, Driveway Parking, Wireless Internet, Audio System, Upstairs Game Room, Private Washer/Dryer, Fishing Dock (no boats permitted), 2 Kayaks for Guest Use, 4 Bikes for Guest Use, Keyless Entry, Private Assoc Beach Access less than 12 Min Walk Away, Outdoor Security SystembrBedding: 2 King Beds (Master and Off Kitchen Guest Suite) + 2 Queen Beds (Downstairs Guest Bedrooms) + 1 Full-over-Full Bunk BedbrView: Canal ViewbrGarage Note: Guests will not have use of the 1-car garage on the west end of the home. for parking but accessing the kayaks and bikes. The garage on the east end of the home is locked and not accessible.brbrThe Space:brA 4 digit door code will be provided prior to your arrivalbrbrGuest Access:brPrivate entrance. Driveway parking onlybrbrThe Neighborhood:brLocated in the highly desirable Country Club Shores residential community on the south end of Longboat Key.brbrGetting Around:brThe property is 12 minute walk the deeded beach access with pedestrian crosswalk. 10 minute drive to St. Armand's Circle. 20 minutes into downtown SarasotabrbrOther Things to Note:brThere is an instruction book kept in the kitchen on the bar countertopbrbrInteraction with Guests:brHost is available any time if needed.

Villa Sereno Summary:

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$437.8

What's better than your own private paradise Come and enjoy this beautiful, recently remodeled, canal front 2 bedroom 2 bathroom private home with heated pool located within walking distance to the longboat key beaches. Close proximity to restaurants and a neighborhood atmosphere This beautifully updated elevated 2BR/2 BATH block home features a private setting with 100ft of canal frontage. Private dock, with spectacular view. Across the canal is an undeveloped nature preserve owned by the Town of Longboat Key (no homes).br Fully screened back patio with tons of comfy seating provides ample space for indoor/outdoor living. brThe outdoor area features two lounge chairs, sofa seating with fire pit and additional dining table by the water so you can easily watch for manatee or dolphins.br But, that's not all, there is also a dock so you can bring your boat or rent one from a local marina, do a little fishing or launch kayaks (ask Michaela about the rent)The dock is also equipped with a 10,000 lb. boat lift which is available for use for a small fee to have the lift bunks adjusted to your boat. brMaster Bedroom features a king size bed, 55 smart HD TV and en-suite bathroom.brGuest room features 2 twin size beds , 43 smart HD TV. Fully equipped kitchen. Plenty of pool towels, beach towels and more.....brBEACH ACCESS across Gulf of Mexico Drive on Gulfside drive across from Christ church. We provide a beach wagon, beach chairs &umbrellas.brTo heat the pool during the winter time, we charge $150/week.

Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

Longboat Key, Florida, United States

3

Bed

Bath

6

Sleeps

$226.95

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 and built in ovens. Reimagined master, stone solid surfaced kitchen counters, unique wood high end cabinetry, exquisite window treatments. br 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 , clubhouse, 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 unitbrbrRental includes Cable tv, Wifi, parking, water and electric.brbrManaged by FGC Vacation Rentals

Beachplace 7 - 202 by FGC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$302.57

Discover a newly renovated beachfront sanctuary where Tommy Bahama-inspired style meets modern luxury. This 4th-floor retreat features travertine marble floors, granite countertops, and custom cabinetry throughout. Relax on your private lanai as the sun sets over the Gulf of America, or spend your days enjoying our heated beachside pool, private tennis and pickleball courts, and exclusive beach access.brAdventure awaits with bay access for kayaking and fishing, and Bayfront Park just across the street. When you aren't exploring, unwind in the spacious living area featuring smart TVs, a new Bassett sectional, or retreat to the master suite with its own private balcony and spa-like walk-in shower. Located just seven minutes from the world-class dining of St. Armand's Circle and the cultural gems of Sarasota, this is the ultimate tropical lifestyle.

Exquisite Beachfront Condo with both Sunrise & Sunset Views

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$258.34

Welcome to Bay Dream Believer, your elegant bayfront retreat on beautiful Longboat Key, Florida. This stunning 2-bedroom, 2-bathroom condo offers panoramic views of Sarasota Bay through massive floor-to-ceiling windows and an enclosed patio that lets you enjoy the scenery year-round. With public beach access just across the street, you’ll experience the best of both worlds — tranquil bayfront living and easy access to the Gulf sands.brbrStep inside to discover a tastefully upgraded interior featuring modern finishes, coastal-inspired décor, and an open layout filled with natural light. The fully equipped kitchen has everything you need to prepare meals at home, while the spacious living and dining areas are perfect for relaxing or entertaining. Both bedrooms are designed for comfort, with the primary suite showcasing incredible bay views and a peaceful ambiance.brbrThe community offers resort-style amenities including two heated swimming pools, convenient elevator access, a fitness center, community kayaks, tennis and pickleball courts, and scenic walking paths along the bay. Reserved parking adds convenience, and pets are welcome upon approval so you can bring your four-legged family member along.brbrWhether you’re here for a short getaway or an extended stay, Bay Dream Believer delivers the perfect mix of comfort, luxury, and coastal charm. Enjoy easy access to St. Armands Circle, Lido Key, and Anna Maria Island, where you’ll find endless shopping, dining, and entertainment options — all just minutes away.brbrBook your stay at Bay Dream Believer and experience why Longboat Key is one of Florida’s most peaceful and picturesque coastal destinations.brbr15 DAY MINIMUM BOOKING PRIOR TO CHECK IN! Association application requires social security numbers.

Luxury Bayfront Condo | Stunning Views, Pools & Beach Across Street

Longboat Key, Florida, United States

Bed

Bath

5

Sleeps

$508.5

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

Villa

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

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$228.93

LATEST NEWSFLASH FOR BEACHPLACE UNIT 4-404: br* 2025 and Winter season 2026 have been fully booked. First available dates start May 1, 2026. Please inquire for special discounts offered May - Nov 2026. brbr* Winter months (Dec-April) for any year are not available for booking online....sorry.brbr* For your safety, we continue to follow COVID cleaning and safety protocols as established by the American Hotels & Lodging AssociationbrbrALLOW US TO HOST YOU AND YOUR FAMILY FOR A BEACH HOLIDAY:brThis beautifully furnished beachfront condo on Longboat Key, Florida is the largest 2 bedroom unit available in the Beachplace complex...over 1500 sqft. We recently completed a total window replacement project, installing new windows and doorwalls throughout the unit. The views are spectacular....few rental units have this added luxury. We also upgraded the entertainment system in the living room with 60 wall-mounted Sony TV and soundbar....great for movies and sports. Xfinity cable box allows you to log into your Netflix or Amazon Prime accounts and also has DVR service. brbrThis two bedroom/two full bath condo was totally remodeled and renovated, floor to ceiling. It was gutted down to the cement frame and rebuilt with premium, high-end features (more details below). If you value cleanliness, this condo is immaculate....please see my guest reviews. Beachplace is very popular in the summer with European and Canadian vacationers with many families returning year after year.brbrLocated on Florida's Gulf Coast just across the bay from downtown Sarasota, this luxury unit is in the Beachplace complex (building 4, 4th floor) at the south end of Longboat Key. As an exclusive premium gated community, Beachplace has all the amenities including a large heated pool, hot tub spa, tennis courts, exercise gym, clubhouse, walking paths, wireless internet, and much more. But the real reason to come here is the private beach -- 9 miles of sugar white sand, crystal clear water, and plenty of peace and quiet. Stroll for hours, swim in 85+ degree water in the summer, hunt for exquisite sea shells, or fish from the local pier. brbrThis unit offers a King bed master suite, and two twin beds in second bedroom, large screen HDTVs, DVD players, wireless internet, all linens, dishes, etc provided. Washer and dryer are in the unit. The unit is 'turn key' - everything you need is there including fishing and tennis gear. Also there is a spacious furnished patio with views of the Gulf of Mexico to the right, and Sarasota Bay to the left. Enjoy spectacular sunrises or sunsets!brbrThe unit is located on the 4th floor (of 6) and is over 1500 square feet with covered parking included. Our renovation included completely gutting the unit down to the cement frame and modernizing everything with high-end features. Here are some highlights:br• New HVAC system in 2019, includes an ultraviolet disinfection system that kills airborne viruses and bacteria in the air. br• Beautiful kitchen with custom premium cherry cabinets, Brazilian granite counters and backsplash, stainless steel appliances, and porcelain tile floor br• New (2024) LG front loading washer and dryer in unitbr• Hardwood floors throughout - Amendiom Brazilian oak harvested under the principles of sustainable forest managementbr• Master bath with custom-built walnut spa vanity, Brazilian granite top, two graphite vessel sinks, charcoal porcelain tile, multi-head shower with stone tile surround and clear glass enclosure.br• Guest bath with custom-built cherry vanity, Brazilian granite top, patterned glass vessel sink, porcelain tile, Jacuzzi tub / shower with stone tile surround, custom glass sliding door.br• Open design and layout - removed walls, raised ceilings, created an open and bright floorplanbr• Bright lighting throughout with dimmersbr• Casablanca ceiling fans in both bedrooms, absolutely silent with infinitely variable speedsbr• Hunter-Douglas window treatmentsbr• New high-definition flat screen TVs (Sony) and Xfinity cable. On demand options plus access to Netflix, YouTube, Prime Video and more. brbrbrRates are shown below: brbrRATE INFORMATION (per month based on 28 nights.....not including taxes fees):br 2025 2026brJanuary - March............ $ 12300 $ 12500brApril & Dec......................$ 7200 $ 7300brMay - November........... $ 4950 $ 4950brbrAll rentals subject to $165 application fee, $200 cleaning fee & 13% state & local taxesbrbrDiscounts for 3 or more month rentals.....inquire for special quotes.brbr* Summer holiday vacationers from UK, mainland Europe, and Canada receive a special treat. Inquire for details.

Upscale Beachplace Condo...availability starting in May 2026....please inquire

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$757.41

Welcome to Longboat Dream! Professionally managed by Gulf Coast Vacation Rentals, experience this brand new 3-story residence on Longboat Key offering the ultimate in luxury and relaxation. Boasting a private pool and spa, this oasis is just steps away from private beach access at the end of the street.brbrMain Level: As you enter, the main level greets you with a spacious garage and sliding glass doors that lead to the fenced-in yard. Here, you'll find the sparkling pool and spa, complemented by an outdoor dining table and plenty of chaise loungers for soaking up the Florida sun.brbrInside, the open-concept living area is flooded with natural light from large windows, creating an inviting and airy atmosphere. The living room features a comfortable L-shaped couch and two additional day chairs, perfect for lounging or entertaining. Adjacent to the living room is a chef's dream kitchen, complete with a large kitchen island, top-of-the-line appliances, and a lovely dining table. A convenient half bathroom is also located on this level.brbrThe first bedroom, also on the main level, offers a king-size bed and an attached bathroom with a gorgeous walk-in shower, providing a private retreat for family and loved ones.brbrTop Level: The top level houses the laundry area with a washer and dryer for your convenience. At the end of the hall, the primary bedroom awaits, featuring a king-size bed, a desk for setting up your remote office, and an attached spa-inspired bathroom. Indulge in the dual vanity and the giant walk-in shower with dual shower heads for a truly luxurious experience.brbrThe third bedroom is perfect for kids, with double bunk beds accommodating four twin beds and an attached bathroom with a stunning shower/tub combo. The fourth bedroom offers another king-size bed and an attached bathroom with a shower/tub combo, ensuring comfort and privacy for all.brbrEvery detail in this home exudes a lovely coastal and welcoming vibe, allowing you to truly relax in paradise. Nothing was overlooked in the design, ensuring that your stay here will be nothing short of extraordinary.brbrThere is an 85 TV in the main living room and 55 TV's in all of the bedrooms. brbrThere are outdoor deck space on each level including rooftop deck, that has two chaise loungers for you to soak up the Florida sunshine, a table perfect for dining while looking over the view of the water. brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties.brbrFurry friends welcome! Up to 2 pets allowed. A non-refundable pet fee applies and must be paid directly to the management company.brbrPrivate beach access is down at the end of companion way, next to Sea Twig Condominiums. brbrPool heating is optional, for an additional non-refundable fee of $25 per day + taxes to be paid directly to the management company after the reservation is confirmed. Pool heat request made after guest arrival will incur an additional $45 trip charge. The pool & spa cannot be heated at the same time.

Luxurious 4BR pool home on Longboat Key steps to the beach - Longboat Dream

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$462.36

Sand Cay resort is using the industries best practices and guidelines to ensure that all CDC sanitizing guidelines are carried out completely. Moving forward we will use only a EPA-registered product, qualified for use against against SARS-CoV-2, the novel coronavirus that causes COVID-19. br. We are centrally located on beautiful Longboat Key, next to the new Zota hotel with it's great restaurants and bars. Our resort has an immaculate white sandy beach, heated pool, shuffleboard, basketball and full tennis/pickle ball court. We have a free laundry room next to the pool, a large barbecue area and an elevator. Our remodeled unit features a fully equipped kitchen with stainless steel appliances, living room with a 52 inch smart HDTV, HDTV in each bedroom and a dining room that seats six. We have a king bed in the master bedroom, two twin beds in the second bedroom and a queen size sleeper sofa in the living room. The private balcony has seating for four with views of the garden, pool and Gulf.

2/2 GULF SIDE APARTMENT, DISCOUNT NIGHTS IN APRIL AND MAY. GULF & BAY VIEWS.

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$271.13

Welcome to your island getaway at 6960 Poinsettia Avenue, a bright and breezy 2-bedroom, 2-bath home just a short stroll from the beautiful beaches of Longboat Key. This laid-back coastal retreat is all about comfort, sunshine, and easy island living.brbrInside, you’ll find an open, airy floor plan with plenty of natural light and a relaxed beach-house vibe. The kitchen is fully equipped for casual meals at home, and the cozy living area is perfect for lounging after a day on the sand. Step outside to your private patio surrounded by tropical greenery — the perfect spot for morning coffee, or unwinding under the stars.brbrYou’ll love how close you are to everything — the beach, local restaurants, island shops, and even nearby St. Armands Circle are just minutes away. Whether you’re here to soak up the sun, paddle through the bay, or simply slow down and enjoy the island pace, this charming home makes the perfect Longboat Key escape.brbrHighlights:br2 bedrooms / 2 bathroomsbrShort walk to the Gulf beachesbrPrivate patio with tropical landscapingbrBright, open living spacesbrClose to restaurants, shops, and island attractionsbrPets AllowedbrbrAccommodations: 2- Bedroom, 2- BathroombrbrLocation: 6960 Poinsettia Ave. Longboat Key, FL 34228brbrBedding: Queen in primary, Queen in guest, Queen sleep sofa in living roombrbrView: GardenbrbrMinimum Night Requirements: 30 day minimumbrbrPet Policy: An additional pet fee will be added to applicable bookings. To reserve a pet-friendly booking contact our local team or select the additional pet fee at checkout. Pets not given prior approval will not be accepted.

Casa Poinsetta- 2BR in a Quiet Coastal Neighborhood by RVA.

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$605.02

Beautiful partial beachview unit on the 2nd floor with lake view and Beach View. Hard to find beautifully appointed 3 bedroom, 2 bath unit with a real feel of home. King Bed in Master, King Bed in 2nd Bedroom and 2 twins in 3rd bedroom. Washer/Dryer in the condo. Come to your home away from home and enjoy.brNewly remodeled kitchenbrNew Windows/Doors have just been installed! Not yet showing in the pictures.brbrbrThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brRental includes Cable tv, Wifi, parking, water and electric.brProperty books by the calendar month

Partial Beach View 3 Bedroom Condo

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$418.43

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway, which includes your beach supplies. It’s 1 block to the beach access, great restaurants and a deli, Also Included is membership and access to Cedars East Tennis Club, which includes a junior Olympic POOL, Pickleball Courts, world class tennis courts, pickleball courts, 24 hour gym and tiki bar, also a 5 minute walk away. Minutes to Holmes and Coquina Beaches.brCentrally located on Longboat Key, with the casual lifestyle, home is located on a quiet street that dead ends at a canal with bay. It’s 1 mile to the beach access it’s a block to Great Restaurants and Shopping! Walk to 32 acre Durante Park - a beautiful coastal hammock forest. Take a bike ride to Bicentennial Park or enjoy shuffleboard, basketball, soccer, tennis and more at the Bay Front Park Recreation Center. Welcome to Paradise! Only minutes from St. Armand’s Circle Cozy beach house has a private backyard with outdoor seating and fire pit. There is a gas grill for grilling your meals. The outdoor shower is a great way to rinse off in nature. The front porch offers a nice place to have your morning coffee.

Longboat Key Beach House

Longboat Key, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charming wooden boardwalk that extends to the back of the property. Hugged by lush landscaping and featuring a spectacular swimming pool, Sea Twig is a paradise beach getaway. This two-bedroom, two-bath unit is beautifully furnished in Florida pastel decorations. Enjoy the hardwood floors, full-sized kitchen, private lanai, and community pool.brbrbrbrAccommodations: Two-bedroom, two-bathbrbrbrbrAmenities: Private Lanai, Grill, Wireless Internet, Full-size Kitchen, Community Pool, Washer/Dryer, Beach AccessbrbrbrbrLocation: 5645 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Requirements: Restrictions Apply

Gulfside Escape at Sea Twig #103- Relax & Unwind Steps to Sand & Pool by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$403.94

There are no ratings and reviews because this is my new property. However, I am a Premier Host with a 5-star rating and excellent reviews, which can be checked here: www.vrbo.com/4425713 for reference.brbrPlease note: Cancellations are subject to a 4% credit card transaction charge.brbrA luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. br This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. brWhile the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.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.

Sunset and Beach view unit 402

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$288.29

Step into tranquility with Longboat Village Getaway, a charming two-bedroom, two-bathroom stilted home nestled on the peaceful residential side of Longboat Key. Situated within walking distance of the Longboat Key Center for the Arts, where creativity flourishes, you'll relish in the serene ambiance this vacation retreat offers.brbrbrbrRecently updated with clean, contemporary furnishings and amenities, and just a brief stroll from the renowned Longboat Key beach, this spacious home is perfect for families, groups, couples, or anyone seeking ample space to unwind in paradise.brbrbrbrFeaturing wireless Internet access, a fully-equipped kitchen, private balconies off each bedroom, a loft media room, a cozy den for additional guests, and a convenient private washer/dryer, Longboat Village Getaway provides everything you need for a memorable vacation experience.brbrbrbrEscape to your own slice of paradise - book your stay at Longboat Village Getaway today and embrace the bliss of Longboat Key's tranquil surroundings.brbrbrbrAccommodations: 2-Bedroom, 2-BathroombrbrbrbrLocation: 7080 Longboat Drive North, Longboat KeybrbrbrbrAmenities: Private Balconies off each Bedroom, Wireless Internet, Full-size Kitchen, Loft Media Room, Pets Allowed (with restrictions), Washer/Dryer Availability, Private LocationbrbrbrbrBedding: 1 King in Master, 1 Queen in Downstairs Guest Bedroom + Sleeper Sofa in DenbrbrbrbrView: Garden ViewbrbrbrbrMinimum Night Requirements: Restrictions ApplybrbrbrbrPet Policy: An additional pet fee will be added to applicable bookings. To reserve a pet-friendly booking contact our local team or select the additional pet fee at checkout. Pets not given prior approval will not be accepted.

Charming Longboat Village Hideaway–2BR in a Quiet Coastal Neighborhood by RVA

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$319.64

Kick off your shoes and settle into the easy rhythm of coastal living. Start your mornings with a stroll along the soft sands, spend the afternoon exploring the island or lounging in the sun, and wrap it all up with a front-row seat to one of Longboat Key’s legendary Gulf sunsets—drink in hand, sea breeze in your hair, and not a care in the world.brbrThis charming Cape Cod-style cottage blends cozy comfort with classic beach style, making it the perfect retreat for couples, families, or small groups.brbrInside the Cottage:brPrimary Bedroombr• King-size bed for a restful night’s sleepbrbrLiving Roombr• Queen sleeper sofabr• Fireplace for a cozy touch on cooler nightsbr• Plenty of space to relax, read, or playbrbrKitchenbr• Galley-style with full-sized appliancesbr• Stocked with all the basics—just add groceries and good companybrbrWildlife, Waves & That Old-Florida MagicbrLongboat Key is teeming with natural beauty. Don’t be surprised if you spot wild parrots overhead, a tortoise crossing your path, or one of the island’s famous peacocks showing off. The cottage’s relaxed vibe fits right in with the local charm and lush surroundings.brbrGood to Know:br• Stairs required to access this cottagebr• No pets, no smoking or vaping, and no partiesbr• Must be 21+ to rent and check inbr• Refundable security hold required at check-in (see details)br• While we aim to keep all amenities in great shape, maintenance may occur—we resolve issues quickly and professionally.brbrOnsite Office Hours:br• Monday–Friday: 8 AM – 4 PMbr• Saturday: 9 AM – 5 PMbrbrThis is your invitation to slow down, breathe deep, and enjoy the simple pleasures of the Gulf. Your beachside cottage is waiting.

Cottage

1BR Gulf Breezes & Old Florida Charm

Longboat Key, Florida, United States

Bed