Longboat Key FL Real Estate & Homes for Rent

This EXQUISITE 3 bedroom - 3 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14' ceiling's perimeter creating a dramatic living space. The entire condo has been renovated incorporating the latest in design, trends and materials. A few of the highlights are: custom "barn doors", custom kitchen cabinetry with floor to ceiling pantry space, state of the art appliances and a quartz countertop, a wine fridge and custom bar space, new recessed lighting and spectacular light fixtures, master suite complete with custom closets, king size bed and a breathtaking bathroom, a guest bedroom with an en suite bath. All of this with outstanding, breathtaking views of the Gulf, Bay and Golf Course. You won't find another unit like this on LONGBOAT KEY. Schedule an appointment to visit today. LUXURY, GULF OF MEXICO, SARASOTA RENTALS, LONGBOAT KEY.

*Rented for Season 2025* Welcome to peaceful Buttonwood Harbour, composed of 50 homes in one of Longboat Key's oldest and sought-after communities. Situated in the middle of Longboat Key, it is walking distance for most, to Publix, the Shoppes of Bay Isles, Tennis, post office, and CVS. Full of friendly neighbors and a favorite place for nature lovers. Boaters and fisherman will be happy with accessibility to the BHA boat ramp for launching and ability to dock your boat at the house during your stay, even utilize the kayak storage if you decide to rent them. No bridges from Buttonwood Harbour out to Sarasota Bay's open waters. Enjoy the day at Bayfront Park, 1.4 miles from the house. Amenities found at Bayfront Park include a 1,350 square foot indoor Recreation Center, a playground, a basketball court, shuffleboard courts, a multi-purpose open field, 3 dedicated pickleball courts, a tennis court, picnic tables, restrooms, and parking for a Town public beach access located across the street. The Bayfront Park Recreation Center is a public recreation facility run by the Town of Longboat Key. You will also find a dog park for your fur babies. This well maintained home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Inside utility room, open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals or visit the many wonderful restaurants on LBK and St Armand Circle. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into the crystal clear deep end. Plenty of new stone pool deck on the offered lounge chairs to bask in the Florida sun. Fabulous teak furniture for outdoor dining and entertainment. The 8 person dining table and cushioned sofa will draw you outdoors. You will be delighted with spending time at this wonderful location and amazing home.

LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. A five minute walk to shopping & pharmacy. Short drive to St. Armand's or downtown Sarasota, for restaurants , theaters and boutique shopping. SARASOTA FL.BEACHFRONT,GULF OF MEXICO,RENTAL,SEASONAL,LUXURY

Available 2025 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness center and tennis courts plus. 24 hr. Concierge and garage parking. Recently painted, new flooring in bedrooms and kitchen. Short distance to St. Armands circle with upscale shopping and restaurants or drive to downtown and enjoy symphony, opera, ballet, live theater and a variety of restaurants to suit most palates.

Available January 2025. Leased February - April 2025. Available May 1 - January 31, 2025. New beautiful renovated kitchen in 2023. SEASONAL/ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. The Large primary bedroom has a King bed and bathroom with a walk-in shower with his/her sinks and a separate seating area. Ample storage available with a large utility closet and a stackable washer and dryer. Guest Bedroom has 2 twin beds and an adjoining bathroom.Amenities include a 24 hour manned guard gate, private beach access, Wi-Fi, lighted tennis courts, pickleball, heated pool and hot tub, two state of the art fitness centers, and BBQ gas grills by the pool. This condo comes with 2 parking spaces - one inside the building close to the elevator and the other outside. Minutes to St. Armand's Circle for first class shopping and dining. Off-season guests pay the monthly electric bill. Sorry, no pets or smoking permitted.

AVAILABLE. 2025 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views from the master lanai. Unit has a washer/dryer and 2 full baths. Feel free to bring your small dog as well. Easy access to St. Armands Circle and Bradenton Beach.

AVAILABLE 2025 SEASON! AVAILABLE APRIL 2024-DEC.2024 This unit has been remodeled with all new furnishings. This is a first-floor walk-down two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space and two balconies. There is a screened balcony/lanai and an open exterior private balcony/lanai. There is a staircase entrance to the front door of the unit as well as a staircase entrance to the exterior balcony/lanai which opens in the screened balcony/lanai. The unit has partial water views from the Living Room, Dining Room, den and the screened balcony and exterior open balcony/lanai over the tennis courts and grounds to the marina and bayou/bay. This is 'old Florida' at its best in ambiance and lifestyle. There are two lighted tennis courts, a community pool and hot tub, a community exterior shaded deck for eating, grilling and relaxing. There is a kayak launch as well. Ask about 2 week minimum rentals in low season months.

Rented for All of Season 2025. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floorplan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy flooring, this home has it all. Sit outside on the upper deck with a view of the refreshing pool during breezy afternoons or the covered deck downstairs which offers shade while not sunning. Ping pong and bocce ball complete the picture for hours of fun. The dining table sits (6) with (4) breakfast bar seats nearby. Two bedrooms have (1) Queen and (1) twin each, one quest bedroom has a Queen and the master has a King bed, all with large screen televisions.

Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Seasonal, furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer. The master bedroom features a queen bed, walk-in closet and ensuite bathroom; second bedroom features twin beds. The spacious living and dining area opens to a private outside patio. If you enjoy an active lifestyle, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will entice you to utilize the available kayaks, boating and fishing pier, as well as private access to the sandy beaches of the Gulf of Mexico. In addition to the over-sized heated pool, Beach Harbor Club has a new fitness center and a library/media room. Elevator accessible and assigned parking complement the amenity package. Enjoy Florida living at its best!

This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views.This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can't be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered parking.As you step into this beautiful 2 bedroom 2 bath turnkey furnished condo, you will find tiled floors throughout and a split floor plan. The large family room has beautiful views of the Gulf, from the sliding glass doors that open to your screened-in balcony. Cable & Wi-Fi Included. There is a gorgeous chandelier over the quaint dining table with 4 chairs, where everyone can gather for a wonderful meal.The kitchen boasts gorgeous granite counters and white cabinetry a ceiling fan, & recessed lighting.The Master has a King-sized bed, TV, & opens to the balcony. The en-suite Master Bath offers double sinks, a shower stall and large walk-in closet. The adorable guest bedroom boast 2 twin beds to share, a ceiling fan, and a guest bathroom with tub/shower. Ideally located near everything the area has to offer, including world-class dining & shopping of historical St. Armand's. There are plenty of outdoor activities as well to keep you busy, such as kayak rentals, bicycle rentals, and take a quiet stroll through Bayfront Park. Your quaint & cozy retreat awaits you! Sorry, no furry friends thank you.

FULL GULF VIEWS from this 12th floor condo at Islands West on Longboat Key. This 2 bedroom, 2 bath unit comes turnkey furnished including flat screen TV's and WiFi. The large master suite features a King sized bed, a large closet and breathtaking Gulf views and the ensuite bathroom has a large walk in shower. You will find the guest bedroom to be quite comfortable and features Queen sized accommodations and also has gorgeous views of the Gulf. The guest bath has a shower/ tub combo. The kitchen has been nicely updated with stainless steel appliances and granite counter tops although you may prefer dining out at one of the area's hot spots. If you're looking for light and bright with priceless views, you won't want to pass on this one. Community amenities include a large heated lap pool and spa, fitness room, clubhouse with cable TV and catering kitchen, outdoor grills, tennis courts, and direct beach access with beach chairs and umbrellas. Islands West is the ideal location. Located at the intersection of the Publix Shopping Center on the Gulf Side at the southern end of Longboat Key. Very convenient to shops and dining and just a short drive to St. Armand's Circle or Downtown Sarasota.

Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for the occasional guests. The condo comfortably sleeps 6. This beachfront community features a large, heated swimming pool, fitness rooms, bicycle racks, and a clubhouse with a catering kitchen perfect for get-togethers. Conveniently located across from the Centre Shops and just a short drive north to the famous Beer Can Island or drive south to St. Armand's Circle and downtown Sarasota. The possibilities are endless! Perfect for an extended stay.

Seasonal. Welcome to the popular Country Club Shores community on South Longboat Key. This 3 bedroom, 2 bath European-style, canal front home features streamlined furnishings, granite bathrooms with rain showers, updated kitchen with sleek stainless-steel appliances, an open living area, terracotta tile and wood floors, heated pool, boat dock, 2 car garage and private beach access. $250 cap on electric. This spacious vacation home is large enough to accommodate up to 12 with 2 king bedroom suites, 2 queen beds in the third bedroom, queen Murphy bed and sleeper sofas. If traveling with your furry friends, this is the home for you, as it is pet-friendly and will accept larger pets.

LUXURY LIVING...behind the gates of LONGBOAT KEY CLUB. Spacious two bedroom, 3 bath condo with a FABULOUS VIEW OF THE GULF OF MEXICO and the SARASOTA BAY FRONT. A huge wrap around balcony to enjoy your morning coffee and beautiful sunsets every night. Conveniently located, a short distance from restaurants and shopping on St. Armand's Circle. A few minutes drive to downtown Sarasota with our expansive theatre district, casual and fine dining rows of shopping. King bed in the master and a queen bed in the guest room. If it's comfort and luxury your seeking for your vacation...you've just found it! GULF OF MEXICO, SARASOTA VACATION PROPERTY, SARASOTA BAYFRONT, LUXURY.

Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous property. Enjoy your morning coffee while sitting on the screened lanai that looks out over the bay. Community amenities include private beach access, pool, tennis courts, clubhouse, kayak launch and BBQ area. Call today as this will not last long!!!

SEASONAL; From floor to ceiling - you'll just love the magnificent views from every room in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully renovated with new professionally designed interior. Sip your morning coffee on the lanai with new glass railings as you plan your daily adventures. Escape to the tranquil master bedroom with exquisite bedding overlooking azure waters with sitting area and ensuite master bath. Entertaining is a delight in the gourmet kitchen with stainless appliances. The light and bright living room features exquisite leather seating area with state of the art digital components including 65-inch TV and DVR. For your added enjoyment there's a dedicated desk with computer and printer, full size - awesome - washer and dryer, built-in closet systems, wifi, large screen smart tv's for guests and covered parking. Live the life you've always imagined with resort-style amenities that include a gulf side heated pool, har-tru tennis court, updated social room and state of the art fitness area and kayak and paddle board & bike storage. Conveniently located to shopping, dining, St. Armand's Circle and downtown Sarasota and the Arts. No pets or smoking permitted. JAN - MAR 2025 ALREADY TAKEN.

Stunning Portobello Vacation 2/2 Condo on Longboat Key. AVAILABLE JAN-APR 2025. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style dcor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes and HD Extreme channel lineup, king size Master bed and guest bedroom provides two double beds, in unit washer and dryer for convenience. One assigned parking space and guest parking available for second car. WiFi and cable package are provided. Heated swimming pool, tennis court and boat dock located conveniently across the street on the bayside of the complex. Only 1/2 mile to Publix shopping and dining center and approximately 5 miles from fabulous St. Armand's Circle. Sorry no pets permitted (no exceptions). No smoking permitted. Off Season $4800. 13% sales and tourism taxes apply for any rental less than 6 months.

LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.

Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat screen TV's, wireless internet and in-unit washer and dryer. Amenities abound at Beachplace including a junior-sized Olympic pool, kiddie pool, spa, tennis courts, grilling areas, clubhouse, and fitness center. Walkers or joggers will love the lush landscaping and extensive (1450 lineal feet) private beach. St. Armand's Circle's shops and restaurants is less than a 5 minute drive and downtown Sarasota with its arts and culture is less than a 15 minute drive. If you simply want to relax, beach umbrellas and chairs are laid out daily for your relaxation. Simply enjoy! No pets or smoking allowed.

SEASONAL :Just you and the Gulf! Enjoy breathtaking sunsets from this lovely 2 bedroom, 2 bath direct Gulf condo with views from every room. Newly renovated, well appointed and can accommodate 6 comfortably with queen-sized pull-out sofa in the living room. Relax, unwind, fish, take a dip in the pool, walk the beach or simply chill with your favorite beverage. Close to everything...shopping and restaurants are a short stroll or drive. St. Armand's is less than a 10-minute drive, downtown Sarasota 15 minutes away and Anna Maria approximately 20 minutes or so. Enjoy cooking, watch the sea birds and listen to the waves while preparing a sumptuous meal. Privacy galore...the master bedroom features a king size bed, personal bath and walk-in closet. Your guests will enjoy the comfortable guest room with twins, desk and TV armoire. Your home away from home includes is well-stocked and offers wifi, flat screen TV's and washer/dryer. No smoking or pets are permitted, Beach chairs await, just bring your suit and sunglasses! Booked DEC - APR 2024.

SEASONAL: AVAILABLE FOR 2025 SEASON! All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the perfect Winter getaway. One visit to this 3BD+Den/2.5BA golf course detached home will have you wanting more! It has been updated in all the newest tones, is fresh, and combined with natural lighting, is so inviting. Pavered drive and lush landscaping and walkway lead you into the foyer entry. The combined living/ dining area is warm and inviting with vaulted ceilings, tile flooring and new comfortable furnishings. The kitchen is designed for entertaining or just relaxing with a marvelous view of the 2nd green. The den is a cozy retreat for TV or for catching up on work or emails in the dinette area. The private and spacious master suite offers ensuite bath and has a seating area to relax and enjoy the views! The second bedroom features queen accommodations and the third bedroom offers twins. All have their own private entrance for a relaxing stay. Additional charges for pool heater use. This marvelous turnkey residence comes complete with gated security, Wifi, inside laundry, 2 car garage, private and community pool and easy access to shopping, dining and cultural arts from St. Armands Circle to downtown Sarasota. 60 DAY MINIMUM REQUIRED.

Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Master Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive white sand beach on the Gulf of Mexico.

End unit beautifully turnkey furnished townhouse in Fairway Bay of Longboat Key. Lovely decorating in this light and spacious unit that has a view of the canal. Lots of windows and two stories with skylights giving the unit loads of light. Living room is two stories with a vaulted ceiling. Two primary suites with King and Queen sized beds, two dens with double fold out couches. One of the primary suites is on the main living area. Private garage and tenant will have access to one garage parking spot. The unit has two stair master chairs from the garage to the first floor. Available for a six month minimum booking starting May 15, 2024. Call today as this will not last long!!

Gorgeous Bay views await you in this nicely furnished and well equipped two bedroom, two bath, third floor condo in popular Fairway Bay. You will enjoy watching the wildlife frolic in the bay as you sip your morning coffee. There are two twins in the guest bedroom with it's own access to the guest bath, King in the Master bedroom and a large master bath with plenty of closet space. The kitchen has plenty of cookware and dishes and a full size washer and dryer. This vibrant community offers several heated community pools, pickleball and tennis and a newly renovated fitness room. In addition, you will have access to the private Beach Club located at 2111 Gulf of Mexico Drive. This gated beach club has full facilities and ample parking, gas and charcoal grills and volleyball. Booked for January, February, March and April of 2024.