Longboat Key Vacation Rentals, Private Homes & Condos for Rent.

Apartment in Longboat Key

*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 .......

5.0 Star Review

Apartment in Longboat Key

*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 th.......

4.7 Star Review

Apartment in Longboat Key

*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.......

4.9 Star Review

Private Vacation Home in Longboat Key

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 fantas.......

4.5 Star Review

Condo in Longboat Key

. 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
Vacation Rental in Longboat Key

Condo in Longboat Key

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 Outdoo.......

5.0 Star Review

Condo in Longboat Key

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 bedro.......

4.9 Star Review

Condo in Longboat Key

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.......

5.0 Star Review

Condo in Longboat Key

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

2 Bedrooms - Sleeps 4
Vacation Rental in Longboat Key

Villa in Longboat Key

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.......

5.0 Star Review

Condo in Longboat Key

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!

-- TH.......

4.5 Star Review

Condo in Longboat Key

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 a.......

5.0 Star Review

Cottage in Longboat key

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 o.......

5.0 Star Review

Cottage in Longboat Key

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 pr.......

4.6 Star Review

Condo in Longboat Key

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 off.......

4.8 Star Review

Condo in Longboat Key

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 ambien.......

5.0 Star Review

Condo in Longboat Key

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 .......

4.8 Star Review

Condo in Longboat Key

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 unwi.......

2 Bedrooms - Sleeps 4
Vacation Rental in Longboat Key

Hotel Resort in Longboat Key

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 boa.......

5.0 Star Review

Apartment in Longboat Key

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.......

Studio - Sleeps 2
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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.......

5.0 Star Review

Condo in Longboat Key

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 a.......

4.9 Star Review

Condo in Longboat Key

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.......

4.8 Star Review

Condo in Longboat Key

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 ...
.........

2 Bedrooms - Sleeps 4
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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 .......

4.0 Star Review

Condo in Longboat Key

• 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 ame.......

4.0 Star Review

Private Vacation Home in Longboat Key

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 e.......

6 Bedrooms - Sleeps 10
Vacation Rental in Longboat Key

Condo in Longboat Key

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, .......

5.0 Star Review

Condo in Longboat Key

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
Vacation Rental in Longboat Key

Condo in Longboat Key

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.......

2 Bedrooms - Sleeps 4
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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 .......

4 Bedrooms - Sleeps 10
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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 bea.......

1 Bedrooms - Sleeps 3
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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, .......

1 Bedrooms - Sleeps 3
Vacation Rental in Longboat Key

Condo in Longboat Key

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. On.......

4.7 Star Review

Private Vacation Home in Longboat Key

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:

- .......

2 Bedrooms - Sleeps 6
Vacation Rental in Longboat Key

Private Vacation Home in Longboat Key

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........

5.0 Star Review