Longboat Key Vacation Rentals, Homes and Condos for Rent

Longboat Key Apartment 5.0 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Beautifully remodeled and upgraded; condo 5 sits directly on the Gulf of Mexico Beach and benefits from its prime block location offering optimum views of the pool and the gulf.
This fabulous 2nd floor 2 BD/2 BA condo has been exquisitely upgraded to the highest specification. A c.......

2 Bedrooms - Sleeps 6
Apartment in Longboat Key

Longboat Key Apartment 4.7 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.
A first floor 2 bedroom 2 bath condo that offers a view of the pool and Gulf of Mexico from the living area and the screened lanai which includes teak furniture. The primary bedroom offers a king bed and the guest bedroom suite offers a queen bed which has proven to be perfect for two couples with two lar.......

2 Bedrooms - Sleeps 4
Apartment in Longboat Key

Longboat Key Apartment 4.9 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 1-Queen Bed, 1-Sofa Sleeper
Situated in this idyllic resort comprised of eight units, unit 7 features exceptional views of the ocean and pool. Feel the warm breeze flow in from your screened lanai while enjoying your morning coffee, afternoon cocktail or good book!
The spacious open floor plan provides plenty of.......

2 Bedrooms - Sleeps 6
Apartment in Longboat Key

Longboat Key Vacation Rental 4.5 Star Review

This beautiful townhouse house built in the style of the west coast, has been furnished recently with skilful whimsical, bohemian style in the warm colors of pinks and blues. The house is spread over three levels on the first floor and will welcome you with beautiful and soft sofas (bed) positioned towards a veranda terrace directly overlooking the mangrove forest organized with a table and comfortable chairs to enjoy a drink towards the sunset, next to an 55” smart TV and following a fantastic table positioned near a large comfortable couch where 6- 8 people can comfortably sit, the very.......

2 Bedrooms - Sleeps 7
Vacation Rental Home in Longboat Key

Longboat Key Condo

. The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise........

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

Welcome to Paradise at LBK Getaway! Great opportunity to stay at an exquisite 2-bedroom, 2-bathroom villa style home in the coveted north end of Longboat Key. Just feet away from the crystal blue gulf water and beautiful pristine sandy beaches. Spend the day catching a wide variety of fish on the fishing piers or building sand castles in the sand. You will also enjoy relaxing in your private garden back yard with Lush Landscaping, Decorative Fencing, Accent Lighting, BBQ Grill and Private Outdoor Shower. Delicious dining and Shopping are right around the corner. Maybe you prefer golf, tennis, .......

2 Bedrooms - Sleeps 5
Condo in Longboat Key

Longboat Key Condo 4.9 Star Review

The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box, Nespresso coffee machine, flat screens TV's in every room (65" and 32" in bedrooms) and free WiFi. The Master bedroom has a King and the Guest bedroom a Queen and XL Twin. Two bathrooms and a well furnished kitchen, washer/dryer. You may sun, relax.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

All the comforts of home in this one bedroom, one bathroom condo with killer views. Located on Whitney Beach, this condo is in a beautiful, quiet, and uncrowded area of Longboat Key located on the second level. The condo offers immaculately groomed grounds, pools, tennis courts, a barbecue area, and the use of a private dock the Bayside. Steps away from the Gulf, it's private, yet close to fabulous restaurants and shopping along Longboat Key and St. Armand's Circle. Relax and enjoy the beautiful sunset each night on the outdoor deck!
30 day lease required by HOA. However, occupancy and rate.......

1 Bedrooms - Sleeps 2
Condo in Longboat Key

Longboat Key Condo

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.
• Private beach access with chairs and umbrellas included
• High Speed Wi-Fi and Cable TV
• Lighted tennis courts
• Heated pool and hot .......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Villa 5.0 Star Review

Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, restaurants, groceries and more. Perfect place for a relaxing beach getaway!

Nestled in a quiet residential complex and centrally located in Longboat key, condo features a fully equipped renewed kitchen with upgraded brand-new stainless-steel appliances, new quartz counter tops, with all cookware/dishes/utensils included. Bathroom completely remodeled with new shower, tiles vanity and toilet. (pictures need to be uploaded)

Living room has a large smart flat screen TV with access to Netflix, local channel.......

2 Bedrooms - Sleeps 4
Villa in Longboat Key

Longboat Key Condo 4.5 Star Review

Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in the Silver Sands Gulf Beach Resort. Boasting a fully equipped kitchen and nestled on the ground floor, this beach escape provides all of the essential comforts paired with convenience for a relaxing stay. Tee off at the green in the morning, stroll to the shore to enjoy the direct beach access, tour the Ringling Museum, and enjoy a sunset view from the private porch!

-- THE PROPERTY --

Community Heated Pool | Outdoor Dining | Smart TV w/ Cable

Perfect for s.......

1 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

A very warm welcome to your beautiful, home away from home on this Island Paradise!

This gorgeous location is truly one of the most relaxing places on the planet, and we know that you are just going to love it!

With views of the gorgeous Gulf of Mexico from the living areas, Master Bedroom and Lanai of our fabulous first floor apartment, you can walk straight out onto the lawn and be on the beach or at the pool in moments!

Furnished in Beach Cottage style, the main living area has an L-shaped sofa which will convert to a Queen size bed. There is a beautiful dining suite .......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat key Cottage 5.0 Star Review

The Bikini bottom Cottage is on an alley way that lead directly to the kayak and boat launch. Walk down to view the sunrise coffee in hand with the Sailboat moorings and end your day at The Mar Vista restaurant. Make sure you walk out on the dock and look in the water around the sunken lights.
Across from The Village is the white sandy beach. Meander down the boardwalk and the beach opens up for miles of tranquil shoreline. The tip of the island feels more like you've discovered your own private island. With old trees laying in the water and no structures in site you can float out .......

1 Bedrooms - Sleeps 4
Cottage in Longboat key

Longboat Key Cottage 4.6 Star Review

Beachfront cottage that is located directly on the Gulf of Mexico and the only thing that is between you and your beach front cottage, are sea oats, palm trees and sand dunes. We are a premier and private beach holiday spot. The property is secluded and private and you are assured a hassle free beach front holiday.

The cottage has a full kitchen, living room, sun porch area, two bedrooms - one king, one full bed, one single bed, a pull out sofa and one bathroom.

Our beach front property is over one acre and is located directly on the beach. There are also 3 additional cottages f.......

2 Bedrooms - Sleeps 6
Cottage in Longboat Key

Longboat Key Condo 4.8 Star Review

Our condo has everything you will need for a relaxing vacation on the beach.

The island of Longboat Key...
... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine. Daytime excursions are numerous, so that your holiday will never be without plenty of activity. Orlando and Tampa, with their fabulous theme parks are within easy reach, and the nearby parks offer the local flora and fauna, and numerous animal attractions such as flamingos and alligators. Shop.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

Enjoy what I call my ‘Million Dollar View’ of the turquoise Gulf of Mexico ocean and sugar white sand from this amazing BEACHFRONT condo. This second story condo is located in the Longbeach complex on the north end of Longboat Key and is located in one of the buildings closest to the beach. (you must be OK with stairs to enter) Live serenely in this pristine location knowing that the party and fun of Anna Maria Island and Bridge Street is north just a couple of miles while the upscale ambience of Longboat key is all around you. There are several fabulous restaurants within walking distanc.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area.
This deluxe unit features almost 1700 sq ft with a 52’ long, beachfront lanai. The oversized living and dining area and both bedrooms open to the lanai. There is a fully equipped kitchen with microwave oven and a washer and dryer. The master bedroom has a king size bed with dressing area and bath. The guest bedroom has two twin/single beds and a dressing area and bath. All rooms are furnished in a contemporary Floridian style.
You will en.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo

Immerse yourself in this beautiful 2 bedroom, 2 bathroom condo just steps away from one of the most beautiful beaches in Florida. Fully furnished and tastefully decorated, this slice of paradise will make you feel right at home on Longboat Key. The original artwork that adorns the walls of this vacation home - created by recognized painters, LED-lit wine bar with modern cooler, and plenty of natural light and tropical breeze offers a tranquil surrounding and the perfect setting to relax and unwind. This 2nd floor unit includes a designated sheltered parking space, and has easy access to elevat.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Hotel resort 5.0 Star Review

MINIMUM RENTAL ONE WEEK:
MARCH 9, 2024- MARCH 16, 2024
MARCH 16, 2024-MARCH 23, 2024

The Veranda Beach Club on Longboat Key offers an unparalleled location right along the Gulf of Mexico's shores. Your arrival promises warm hospitality, engaging activities, and a laid-back island atmosphere.

This five-story elevator building houses a charming 2-bedroom, 2-bathroom unit complete with a fully equipped kitchen. Positioned beachside, it offers stunning ocean views and boasts a lovely, spacious veranda.

Longboat Key is a true paradise with its mesmerizing aqua-gre.......

2 Bedrooms - Sleeps 6
Hotel resort in Longboat Key

Longboat Key Apartment

This is a boat slip. at Harbour Villa Club. Direct access to ICW and Gulf . Up 55 ft LOA. Water included One free month of rent For a six month or longer lease signed between Houzlet publishes listings on Vrbo; which in turn, allows tenants to instantly rent seasonal rentals. Houzlet’s properties are managed by licensed real estate agents. Although the property is an instant rental, it’s possible there can be another pending application. If the home is not available, we can offer you another suitable option or you can cancel for free.


House Rules.
The refundable policy is a.......

Studio - Sleeps 2
Apartment in Longboat Key

Longboat Key Vacation Rental 5.0 Star Review

THIS PROPERTY HAS BEEN INSPECTED BY AND REGISTERED WITH THE TOWN OF LONGBOAT KEY RRR# 00134.2023

*****ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT****PLEASE PROVIDE DETAILED DESCRIPTION OF TRAVELERS WHEN REQUESTING A BOOKING ****

The Pineapple Cottage is a special oasis of tranquility and comfort. Surrounded by the palm trees that symbolize Florida, it is a private home nestled on a canal that leads directly into Sarasota Bay. Our home is situated in the desirable neighborhood of Country Club Shores --- just a short ride from the world class shopping and dining .......

3 Bedrooms - Sleeps 6
Vacation Rental Home in Longboat Key

Longboat Key Condo 4.9 Star Review

Two minute walk to Private Gulf Beach access, no need to cross the street.

This charming unit is the only 2 bedroom ground floor unit in Cabana Beach Club, a secluded, tropical, boutique resort that has all of the amenities for a Romantic Getaway or Family Vacation.

The private patio has an umbrella table and chairs for comfortable outdoor dining as well as a lounge and side table for sunning and relaxing.

NEW hurricane windows and doors make this lovely unit even quieter and more comfortable!

HD cable, Smart TV, Blu-ray/DVD player, CD player, WIFI, central air con.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key!

Magnificent renovated (January 2022) condo with an open 1,132 sq. ft. floor plan, 2 bedrooms, 2 full bathrooms, full kitchen, a large living and dining room as well as a separate sitting room with a queen sleeper sofa. Condo sleeps six.

King bed in master bedroom, 2 twin beds in guest room, queen sleeper sofa, hotel-grade gel foam mattresses in bedrooms, beach chairs, kids pack & play, etc. Highspeed WIFI internet, flat screen internet TV's, ceiling fans in each room (4).......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo

BOOK NOW! AVAILABLE FOR DECEMBER 2023 FOR $ 8500 PER MONTH AND JANUARY 2024 FOR $8500 PER MONTH! Gulf Front Longboat Key Vacation Rental! 2 bedrooms, 2 baths, over 1300 square feet under air, walk right out to the beach from this elegant, yet comfortable home. You will love this updated condo and the coastal inspired decor, it's sure to become your home away from home! Featuring a king bed in the primary bedroom, a I full bed and twin day bed with trundle in the guest bed, 3 flat ...
...screen TV's, Cook's kitchen, and dining for six. Enjoy gorgeous sunsets from the patio or walk out .......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental 4.0 Star Review

Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat docking. The kitchen and bathrooms were fully remodeled in 2023! We're located on a quiet street in close proximity to Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserve.

Relax on your waterfront patio, perfect for outside dining, barbecues and quiet evenings. Bike, Kayak and Paddleboard rentals are available nearby to explore the island and waters. Beach wagon, chairs and umbrella included for your easy 0........

2 Bedrooms - Sleeps 4
Vacation Rental Home in Longboat Key

Longboat Key Condo 4.0 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 area
• Washer and Dryer Conveniently located in unit.
• Master bedroom with a king size bed and beautiful view of the bay!
• Spacious guest bedroom with 2 twin beds
• Large Patio with outdoor seating and a table and direct access to the pool and BBQ.

Harbor Villa Club amenities
• Pool
• Hot Tub
• Tennis Court
• Boat Slips (Rented Separately)
• E.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental

Embrace yourself with pure luxury and privacy, surrounded by lush landscaping and steps from the gorgeous Gulf of Mexico waters! This vacation home is over 4,300 square feet and is perfect for families and executive retreats providing flexibility and privacy for all guests. 4 of the 6 bedrooms have an ensuite. This home provides multiple areas to collaborate and make memories that will last a lifetime. This magnificent home is elegantly decorated and furnished with high-end furnishings to enjoy during your stay and a superior level of cleanliness. Our mission is to make you feel welcome .......

6 Bedrooms - Sleeps 10
Vacation Rental Home in Longboat Key

Longboat Key Condo 5.0 Star Review

Want a beautiful view of the Sarasota Bay from a luxury condo on Longboat Key? This two bedroom second Floor unit with Tommy Bahama Inspired Décor is perfect for a peaceful getaway. This condo is perfect for couples or small families looking to get away from it all.
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.
• Comfortab.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo

55 steps away from the Gulf of Mexico Beach! Beautiful beach with the most amazing sunsets. Family friendly resort with super friendly staff. Plenty of lounge chairs and sun umbrellas, just bring your bathing suit and sunscreen. Special amenities include Pool, shuffle board and miniature golf course........

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo

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 .......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental

Welcome to one of the most picturesque views on Longboat Key. Elegance, privacy and nature abound in this stunning Longboat Key waterfront home that is professionally managed by Florida Vacation Connection. Nestled on half an acre at the bay end of one of Longboat Estates' canals, The Dolphin House, designed by local architect Las Casitas in 2003 and named after the abundance of marine life that can be seen at any given time from the 200 ft of waterfront, is a perfect marriage of serenity and style.
This incredible home is a 4 bed plus den, 4 car garage, Mediterranean-style residence, wi.......

4 Bedrooms - Sleeps 10
Vacation Rental Home in Longboat Key

Longboat Key Vacation Rental

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Daily maid service is provided and laundry services are available, so y.......

1 Bedrooms - Sleeps 3
Vacation Rental Home in Longboat Key

Longboat Key Vacation Rental

Unit Features: 1-bedroom, 1-bathroom unit in the Orange Building Layout Note: Please note, the front door to unit 245 opens into a bedroom space before proceeding into the living areas. We kindly ask guests to take this layout feature into consideration when making their travel selections. View: Pool/Gulf View Bedding: 1 King, Sleeper Sofa Resort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Daily Maid Service, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, .......

1 Bedrooms - Sleeps 3
Vacation Rental Home in Longboat Key

Longboat Key Condo 4.7 Star Review

Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maximum of four adults. Your private community includes lush tropical landscaping and the white powdery beach sand that the Longboat Key is famous for. Only minutes away from Saint Armands Circle, Sarasota and Anna Maria Island. This gorgeous property b.......

1 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental

The spacious bedroom has a larger screen TV and a ceiling fan. Full size washer and dryer in the property , makes longer stays convenient.

SLEEPING ARRANGEMENTS (sleeps 6):

Main bedroom

- 2 Queen beds

- Night stand with reading lamp

- Dresser with smart TV

- Full bathroom with walk-in shower


2nd accomodations

-Queen size bed off living room , with Futon Couch for extra sleeper with privacy sliders


Highlights:

- Fully-equipped kitchen with dishwasher, coffee maker, blender & more!

- Washer & dryer

2 Bedrooms - Sleeps 6
Vacation Rental Home in Longboat Key

Longboat Key Vacation Rental 5.0 Star Review

Comforts of home with a fully equipped kitchen and washer/dryer. New queen and XL twin beds. Bedding and sheets supplied. Enjoy local restaurants, white sand beaches and fish the canal, bay or Gulf........

2 Bedrooms - Sleeps 6
Vacation Rental Home in Longboat Key

Longboat Key Condo 4.4 Star Review

Second floor,.. It's very cozy with all the comforts of home. This renovated unit has an updated kitchen and baths with new ceramic tile. New furniture through out with a flat screen television. Complete beach supplies, toys and umbrellas. Unit sleeps a max of 6 people: 1 queen, 2 twins, 1 sleeper sofa.
Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will become part of our family, and we will look forward to your return year after year.
When planning a trip to the beautiful Gulf Coast Beaches, stay with us. All of o.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

LongBoat Key Cottage 5.0 Star Review

WE ARE RENTING A FANTASTIC KEYWEST STYLE COTTAGE ON THE BEACH OF LONGBOAT KEY FLORIDA JUST STEPS TO THE SANDY BEACH OF THE GOLF OF MEXICO. PERFECT FOR SWIMMING, STROLLING ALONG THE BEACH AND WATCHING THE SUNSET, BUILD SAND CASTLES. IT HAS 3 BEDROOMS, A SOFA BED , 2 BATHS, A LIVING ROOM, DINING ROOM, FULLY EQUIPPED KITCHEN AND A FRONT PORCH WITH ROCKING CHAIRS. THIS RESORT HAS IT ALL. IT IS A 'GOLD CROWN' TIMESHARE WHICH WE CANNOT USE...AVAILABLE ONLY THE WEEK OF March 30 -April 6 2024. LOCATED ON THE BEACH OF THE CALM WATERS OF THE GULF OF MEXICO, THIS IS A PERFECTLY IDEAL SPOT FOR RELAXING;.......

3 Bedrooms - Sleeps 8
Cottage in LongBoat Key

Longboat Key Vacation Rental 4.9 Star Review

Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis / Pickle Ball court. For the boater enthusiasts, enjoy docking your boat/yacht in your private, deep-water dock.

This 4000 square foot home is perfect for entertaining and accommodating all your friends and family. This home offers four large bed.......

4 Bedrooms - Sleeps 8
Vacation Rental Home in Longboat Key

Longboat Key Condo

Whitney Beach 149

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Open up the double glass sliders to feel the balmy bay breezes while watching manatees in the canal at this relaxing Whitney Beach retreat. Situated on the north end of Longboat Key, this beach-to-bay community boasts deeded beach access and a waterfront location on Bishop's Bayou which leads out to Sarasota Bay for boating, fishing, kayaking & paddle boarding. On the gulf side, the Whitney Beach Conservancy offers two tennis c.......

1 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large living area. Living, dining, and bedrooms open to balcony. Designer kitchen with Thermador appliances, dolomite marble backsplash, waterfall dining table, white quartz countertops, and acacia wood paneling. King in Master, dressing area, full bath. 2 doubles in guest, dressing area, full bath. 2 workstations in each room. Guests have access to private beach, pool and hot tub only........

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.9 Star Review

Offered by FL Vacation Connection, this island getaway is located on the southern tip of Longboat Key with beautiful beach views and pool area. Located on the 10th floor, you will enjoy gorgeous views in this beachfront property. The living and dining area and both bedrooms open to the lanai plus you have a full kitchen. Both full bathrooms offer tub and shower combinations. The master bedroom has a king size bed with dressing area and bath. The guest bedroom has two xtra long full size beds, a dressing area and bath. All rooms are furnished in a contemporary and Floridian style.
You w.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 4.7 Star Review

Tastefully renovated, non-smoking, second floor unit. New updates every year. Light and bright with all the comforts of home! Lovely furnishings. Fully equipped new kitchen. Italian style tiles throughout the unit. Tempur-pedic mattress in master bedroom and walk-in shower. Amenities include: three HD (1080) LCD televisions in all rooms, DVD Stereo, CD, Blue Ray DVD player in living room, high speed internet, and an office!

You will miss nothing in this unit.

Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will bec.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.9 Star Review

Beautiful 2 bedroom 2 bath condo on the 2nd floor featuring over 1200 sq. with a beach theme. This unit was recently remodeled with new paint, new floors, appliances and granite counter tops in the kitchen and bathrooms. New furniture throughout. Master bedroom is spacious with a comfortable king size bed and en suite with a large tv. Guest bedroom features 2 queen beds with blackout drapes to ensure a wonderful nights rest.

After a day at the beach, you can unwind in the den or our living room, which overlooks the pool with a beautiful garden view of the property with palm trees. .......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

Located on the famous Longboat Key, it offers a unique experience with a 180 degree Sarasota Bay view.
Located on Dream Island Rd, this beautiful condo is 1,293 sq ft with 2 bedrooms and 2 bathrooms, on the 2nd floor with an elevator.
It's in the Harbor Villa Club community which is quiet with many available amenities: large heated communal pool with a view on the water, spa and tennis courts.
Public beach access is at a 15 min walk and 5 min by car!

The open-plan kitchen has white cupboards, and is fully equipped with microwave, oven, dishwasher, modern fridge, stove, washer .......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

WELCOME TO Longboat Key, Florida!

Our beautiful PENTHOUSE UNIT at BEACHPLACE, named “Bird’s Eye View”, has a breathtaking full view of the Gulf of Mexico from the master bedroom, living room, kitchen and dining room. The guest room and kitchen look out over Sarasota Bay. The unit was purchased from an original owner and on the market one day...because the view is spectacular.

My husband and I started coming to Beachplace as kids…and we have enjoyed many vacations on the famous powder white sand of Longboat Key. This building is our favorite at Beachplace! As you enter th.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT

This complex is a two-story building with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get, direct beautiful Ocean views.

The ground floor studio features a queen-sized bed, as well as a sofa bed, which can accommodate 2 adults and 1 child. A large walkout private patio with a table, 4 chairs, and 2 chaise lounges allow you to enjoy the white sand beach and the emerald green waters of the G.......

Studio - Sleeps 3
Condo in Longboat Key

Longboat Key Condo 5.0 Star Review

Our building is located on the beach, this unit has an ISLAND view.
Beautifully renovated 1 bedroom, 1 bathroom condominium overlooking the island toward Sarasota Bay. Owner has renovated this condo with the highest quality materials including Starmark Cabinetry, Cambria Quartz kitchen countertops, Grohe fixtures, Kohler shower doors and so much more. This kind of quality is hard to find in a rental unit!
* Enjoy preparing meals in the oversized kitchen, fully equipped with blender, coffee maker, ice maker in refrigerator.
* Stainless steel appliances.
.......

1 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental 5.0 Star Review

This lovely 3 bedroom, 3 bath home waterfront hideaway will take you to another place and time. This treetop house is tucked away in lush native landscaping perched on the water's edge looking out at Longboat Pass. It is the perfect retreat for a couple with small family or three couples. It has a modern, open Scandinavian style floor plan with light hardwood floors, high ceilings bathed in natural light. There are views of the water from almost every room with a large covered wrap around deck facing the Longboat Key pass. This terrace has a lovely seating area with couch and chairs as well.......

3 Bedrooms - Sleeps 6
Vacation Rental Home in Longboat Key

Longboat Key Apartment 4.9 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHFRONT Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Updated stunning BEACHFRONT condo, boasts the prime location at the complex - located on the 1st floor at the very front of the building with the closest direct beach access.
The unit has recently been updated with all the modern conveniences of home, in a luxury vacation rental. .......

2 Bedrooms - Sleeps 6
Apartment in Longboat Key

Longboat Key Condo 4.7 Star Review

We have two units in this condo building. One on the 2nd floor and one on the 7th. Both with magnificent Gulf of Mexico views.

Please 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.

Please look at the title on each photo to see each condo.

Take advantage of the beach at your back door and enjoy this stunning vacation condominium with spectacular views of the Gulf of Mexico, located on .......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.8 Star Review

Spend some time in paradise! Relax in a comfortable Laz Boy Recliner overlooking the Gulf. Enjoy breakfast while watching the dolphins play. Come see picturesque sunsets that seem surreal. Newly remodeled beach front two story condo offers an awesome full gulf view with private terrace. This one bedroom, KING size bed(amazing mattress), one bath condo, has a fully equipped kitchen (cherry wood cabinets, granite countertops, stainless steel appliances)2 flat screen TV's (1 TV in Bedroom & 1 in Living room 42') with DVD. There is also an extremely comfortable Murphy bed (queen size) in a .......

1 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Condo 4.9 Star Review

This large and airy 2 bedroom condo is right on the beach. It is a corner unit on the ground floor and it is very private and peaceful. No stairs - just step right outside. The ideal spot for a relaxing getaway and memorable sunsets.

This easy access ground floor unit offers two-bedrooms, two-bathrooms, a spacious living room, a full-size kitchen, washer/dryer and a private lanai.

The master bedroom has a king size bed and a queen bed. Flat screen tv. The second bedroom has a queen size bed. Free wireless high speed internet and cable. Linens and towels are provided. This roomy.......

2 Bedrooms - Sleeps 6
Condo in Longboat Key

Longboat Key Apartment

Historical neighborhood. Open loft-like space features newly remodeled kitchen/bath, brand new designer queen tempurpedic sofa bed (no bar in mattress) and two twins in a daybed. Walk in closet with shelving. Light and bright w windows thru-out! Brand new front yard and landscaping. This is a nice, quiet, fully furnished guest house with wifi, brand new 18K BTU air conditioner and water filtration system. Here, you'll experience the Old-Florida feel...this area isn't built up by the celebrity-driven craze that draws a huge crowd and the locals intend on keeping it that way! 2 blocks from pier,.......

1 Bedrooms - Sleeps 2
Apartment in Longboat Key

Longboat Key Apartment 4.7 Star Review

Offered by Florida Vacation Connection, enjoy this spacious 650 square feet beachfront Club Suite. This perfect island getaway is located behind the gates on the prestigious southern tip of Longboat. The dressing area is updated with blue Brazilian granite counters resembling the blue Gulf waters and the bathroom with Italian porcelain tile and an onyx inlaid bathtub / shower. The open and private lanai is a pleasant place to take in the view, read a good book, enjoy a cup of coffee, or an evening meal and watch dolphins passing by. Wake up every morning and see the gentle waves of the Gulf .......

Studio - Sleeps 2
Apartment in Longboat Key

Longboat Key Vacation Rental

PLEASE SEE COVID 19 AND STANDARD POLICIES BELOW - it is different from VRBO policy options as are payment options. Arrivals prior to 90 days are to be paid in full. Please note that the minimum lease period a month. due to City Code restrictions. We are not able to make an exception.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.......

3 Bedrooms - Sleeps 6
Vacation Rental Home in Longboat Key

Longboat Key Condo

ABSOLUTELY GORGEOUS INSIDE! Bayport Beach and Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social.......

2 Bedrooms - Sleeps 4
Condo in Longboat Key

Longboat Key Vacation Rental 4.9 Star Review

Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience for you and your family like no other.

The house has 4 bedrooms and 4 bathrooms and an outdoor shower. All rooms view out over the azure waters of Longboat Pass, with 300 feet of beachfront, palm trees, shaded hammocks, and private dock.

Boat Access - Reasonably priced discounted local boat rentals are available for our guests from Cannons Marina on Longboat Key or Bradenton Beach Marina - both a short distance away from the Island in protected well marked Int.......

4 Bedrooms - Sleeps 10
Vacation Rental Home in Longboat Key

Longboat Key Hotel resort

Four Winds Beach Resort is located on Longboat Key Island, just off the shores of Sarasota, Florida. Come enjoy the sandy beach and beautiful sunsets right out your front door.

Four Winds Resort offers heated swimming pool, hot tub, tennis courts, bbq grill, and miles of a sandy beach.

One bedroom is fully furnished and includes a full kitchen with refrigerator, stove, dishwasher and microwave.

Famous Armands Circle and great seafood restaurants located within minutes.

Fly into Sarasota airport or the Tampa and Fort Myers airport.

Disneyland within 2 hour dr.......

1 Bedrooms - Sleeps 4
Hotel resort in Longboat Key

Longboat Key Condo 5.0 Star Review

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT
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This complex is a two-story building with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get, direct beautiful Ocean views.
The ground floor studio features a queen-sized bed, as well as a sofa bed, which can accommodate 2 adults and 1 child. A large walkout private patio with a table, 4 chairs, and 2 chaise lounges allow you to enjoy the white sand beach and the emerald green waters of the Gulf .......

Studio - Sleeps 3
Condo in Longboat Key