sunset Gulf of Mexico
sunset Gulf of Mexicosunset bay sidemapaccess to beachthe beachbeachbeach1 of 2 poolstennis courtspoolbay side of propertycarport/front of  villakitchenkitchenkitchenbathdining room view from living roomliving roomliving roomliving roomqueen bedvanity/walk in closetvanity arealanai
“ Excellent ”
13 Reviews
4860 Gulf of Mexico Dr, Longboat Key, FL 34228



Bedrooms: 1
Bathrooms: 1
Sleeps: 4
Type: Villa
Per month: $2,600 - $3,300
Pets allowed: No
Internet: Yes
Description of the Longboat Key vacation villa rental
Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex situated between the Gulf Of Mexico and the Bay offers a fully equipped 850 square foot ground level villa with carport,clubhouse,2 tennis courts, huge heated pool,fitness centre,shuffleboard,fishing,kayaking,and directly across the street is your private deeded beach.Miles of white sand for morning walks and sunset strolls.The beach is very wide ,shallow,and sandy bottomed so is extremely safe and enjoyable for small children.Just 20 minutes from Saraosta /Bradenton Intl. airport or 75 minutes from Fort Myers Intl.airport.This villa can be rented by the month in January,February,March,and April or for 2 week periods or monthly the rest of the year.

Preference given to multiple month bookings .

Linens, bedding,towels,coffee machine,microwave,toaster,cooking utensils,BBQ,cutlery,,beach chairs,laundry soap,toilet paper,paper towels,etc. all included.UNLIMITED FREE long distance calling to anywhere in the USA, Canada, or Puerto Rico.Villa has a secured wireless internet access.Comfortably furnished and extremely clean.The dining room table seats 4 comfortably.The master bedroom has a queen bed and ensuite 4 piece bathroom with another door from the hallway.All furniture and appliances are less than 4 years old.There is a private washer/dryer.The couch in the living room opens to a queen size bed.Tile flooring throughout with an area rug in front of the couch.The lanai has a table for 4 and is screened by palm trees creating privacy.A bike path runs the entire length of the island ( approximately 10 miles) and two bikes are provided for your enjoyment.There is also a two person kayak provided so you can enjoy quiet paddles on Sarasota Bay where dolphins and manatees are often seen.There is an abundance of great restaurants on the Key and Anna Maria in all price ranges.A grocery store is 5 minutes away.Sarasota is 15 minutes away for museums, shopping, and live theatre.Jet skis, sailboat, yacht, kayak , moped and scooter rentals,golf,dolphin cruises, snorkeling,scuba diving,deep sea fishing,parasailing,horseback riding along the beach,and sunset cruises, are all just a 10 minute drive from the condo.Or just pull up a chair by the poolside and read a good book.All rates in USD.



January $2800
February $3200
March $3200
April, November, or December $2800
May,June,July,August, September , or October $2300
Two weeks in May,June,July,August, September,or October $1500
Two weeks in November,or December $1600
Area Information
Along Florida's central west Gulf Coast and nestled between Manatee County and Sarasota County is the barrier island known as Longboat Key. When you think of a Pristine Paradise, think of Longboat Key.
Longboat Key is the idea beach and bay front setting for the ultimate Florida vacation. Stretching between the gorgeous Gulf of Mexico and serene Sarasota Bay.

The area is appreciated by wildlife as well, so these waters are home to manatee, dolphins, and fish, while pelicans, osprey, and a variety of shorebirds find sanctuary here. There are several parks on the Key to visit for a relaxing afternoon.

Whether you like to spend your time shelling, biking, shopping, fishing or dining, opportunities for these activities are boundless on Longboat Key, Lido Key, and St. Armands Key.

Sarasota’s many cultural centers are only minutes away over the south bridge, including Van Wezel Performing Arts Center, Asolo Theater, Ringling Museum, Sarasota Ballet and Opera, and several other live theaters.

You’ll find terrific shopping on Longboat Key, and St. Armands Key. Anna Maria Island and Bradenton, over the north bridge, both also offer a variety of shopping, theater, and cultural experiences.

Although it is known as a private island, Longboat Key is a popular destination for visitors from around the world. You are welcomed to a plush island of tasteful luxury and tempting quiet pleasures that cater to all personalities. If you are the athletic type, activities on Longboat Key are endless! Shelling, biking, fishing, dining, watersports and rollerblading… just to name a few. Tennis and golf enthusiasts are welcome to take advantage of our first-class Longboat Key Country Clubs. For those seeking a little city life, Longboat Key is only minutes from Sarasota. The city offers many cultural activities from the Van Wezel Performing Arts Center, Asolo Theater, Ringling Museum, Sarasota Ballet to the Sarasota Opera House. Even closer than downtown Sarasota is world-class shopping on St. Armand's Circle, just a bridge away!

Longboat Key is host to many activities. Bask in the tropical sun, play a round of golf, game of tennis, cocktails by sunset, dinner by candlelight or a performance in the city. So many pleasures, so little time….escape to our island!

Florida's major attractions are all within convenient driving distance, including Disney World, Busch Gardens, Sea World and Universal Studios. Enjoy a wide variety of recreational activities including pier or deep sea fishing, boating & golfing. Treat yourself to the world class cuisine and exclusive shops and boutiques in elegant St. Armand’s Circle. Across the bay in Sarasota, you'll find rich cultural heritage alive with superb galleries and performing arts such as the Ringling Museum of Art and the Van Wezel Performing Arts Center.

Key Facts

Longboat Key is an offshore barrier island about 60 miles ( 1 hour ) south of Tampa, Florida.

Orlando ( Disney World) is a 2 hour drive.

The nearest airport is Sarasota/Bradenton International. ( 20 minutes)

Average daily high temperature in January: 72°.

Average daily high temperature in July: 90°.

About the owner

Owner Profile


Availability Calendar



Begins Ends Week
Weekly Monthly Min
Feb 01 2016 Feb 28 2016 - - - $3,300 1 Month
Mar 01 2016 Mar 31 2016 - - - $3,300 1 Month
Apr 01 2016 Apr 30 2016 - - - $2,700 1 Month
May 01 2016 May 31 2016 - - - $2,600 2 Weeks
Jun 01 2016 Jun 30 2016 - - - $2,600 2 Weeks
Jul 01 2016 Jul 31 2016 - - - $2,600 2 Weeks
Aug 01 2016 Aug 31 2016 - - - $2,600 2 Weeks
Sep 01 2016 Sep 30 2016 - - - $2,600 2 Weeks
Oct 01 2016 Oct 31 2016 - - - $2,600 2 Weeks
Nov 01 2016 Nov 30 2016 - - - $2,700 2 Weeks
Dec 01 2016 Dec 31 2016 - - - $2,700 2 Weeks
Jan 01 2017 Jan 31 2017 - - - $3,000 1 Month
View all periods
Check In: 3 p.m. Check Out: 10 a.m.
Deposits: $500 deposit required when booking Balance payable 30 days before arrival date
Payment Options: Cashier's Check, Money Order, PayPal, Personal Check
Other Fees: $100 cleaning fee



  • Beds

  • 1 Queen Bed
  • 1 Sofa Bed
  • Features

  • Air Conditioning
  • Full Kitchen
  • Linens Provided
  • Private Pool
  • Beach Chairs
  • Heating
  • Outdoor Shower
  • Sauna
  • Beach Towels
  • High Speed Internet
  • Parking Included
  • Screened Porch
  • Bikes
  • Kayak
  • Ping Pong Table
  • Wheelchair Accessible
  • Dock/Boat Slip
  • Lanai
  • Pool Table
  • Appliances

  • Alarm Clock
  • Hair Dryer
  • Oven
  • TV (Cable/Satellite)
  • Coffee Maker
  • Ice Maker
  • Radio
  • Telephone
  • DVD Player
  • Iron
  • Refrigerator (Full)
  • Toaster
  • Dishwasher
  • Microwave
  • Stove
  • Washer/Dryer
  • Gas Grill
  • Activities

  • Bicycling
  • Sailing
  • Park
    (1 mile)
  • Volleyball Court
    (3 miles)
  • Boating
  • Snorkeling
  • Shopping Area
    (1 mile)
  • Windsurfing
    (3 miles)
  • Canoeing
  • Tennis
  • Hiking
    (2 miles)
  • Aquarium
    (5 miles)
  • Children's Pool
  • Amusement Park
    (<1 mile)
  • Miniature Golf
    (2 miles)
  • Theme Park
    (5 miles)
  • Fishing
  • Basketball Court
    (<1 mile)
  • Deep Sea Fishing
    (3 miles)
  • Golf
    (6 miles)
  • Gym/Fitness Center
  • Beach
    (<1 mile)
  • Grocery Store
    (3 miles)
  • Horseback Riding
    (6 miles)
  • Kayaking
  • Jet Skiing
    (<1 mile)
  • Live Entertainment
    (3 miles)
  • Movie Theater
    (8 miles)
  • Playground
  • Ocean
    (<1 mile)
  • Parasailing
    (3 miles)
  • Bowling
    (10 miles)
  • Pool
  • Restaurant
    (<1 mile)
  • Scuba Diving
    (3 miles)

Other Vacation Rental Amenities
100 yards to 10 miles of gorgeous white sand beach.The beach stays shallow for quite a ways out so is very "kid friendly."You can walk either direction on the beach for several miles.The villa is located at Windward Bay on a beautifully manicured 27 acre property with fishing and boating docks, fruit trees, gym,men and women's saunas, library, 2 heated pools, 2 tennis courts (night lights),shuffleboard, pool table, ping pong,dart board, all on site.We provide bicycles so you may enjoy touring the island as well as a 2 person kayak.Canoes,kayaks,more bikes, or motorboats can be rented nearby and delivered to the villa.This is a beautiful vacation property with plenty to do in the immediate vicinity or do nothing at all.

Reviews (13)

Reviews for this vacation villa rental in Longboat Key, Florida

Have you been a guest of this property? Write a review!
“ Excellent ”
13 reviews
Bill Mattingly

Bill Mattingly

Carmel, IN USA

Windward Bay Villa, Longboat Key FL

April 16, 2015

Outstanding location for the beach, uncrowded and across the street. two pools available, church nearby along with several nice restaurants. Accommodations were very good. Overalll, a pleasant stay, actually from January thru March.

Dave Leaman

Dave Leaman

Waco Texas

Caught in a pickle

June 3, 2013

After a cancellation at another site we were forced to go on a hunt with only ten days before our flight. Found this gem on line and got in touch with Brad and easily make our vacation plans. This place was above what we imagined. great location on Longboat and villa 1 was great. Had a wonderful two week stay ! We will be back for sure!!!

Marilyn Gagne

Marilyn Gagne


One bedroom villa

April 5, 2013

We really enjoyed staying st this one bedroom villa. The unit was bright and clean and nicely outfitted. Plenty of kitchen equipment and everything you would need. It is located between the two pools in the complex so very convenient to other amenities. It is perfect for a couple.

james monahan

james monahan

New Hartford New York USA

great time

April 5, 2013

The Villa that we stayed in was very nice and clean it had everything there that we needed we enjoyed the pools and the Gulf side very much . We thought that the weather could have been better but I guess the weather has not been good anywhere but overall it was OK just cool in the mornings and it took till after noon to warm up but we were told that this was the first March that is was cooler than normal. But we had a great time and are looking to return next year. Jim & marianne

Gary Hamman

Gary Hamman

Warsaw, Indiana

Windward Bay Villa #1, 4710 Long Boat Key

February 7, 2013

This ground level villa was completely remodeled and had new furnishing and appliances. We spent 1 month and enjoyed every minute of it. The location is perfect for beach access and the pools are also very close to this unit. Everyone was very friendly and helpful. The location makes it easy to get to St Armand's Circle in 15 minutes or almost anywhere on Anna Maria Island in 10 or 15 minutes. We had a great time and will go back.

Penny Huddleston

Penny Huddleston

Springfield, IL

A lovely place to hang your hat!

February 5, 2013

Thanks, Brad, the villa was wonderfully restful. We hung up our clothes, unpacked our bags, and we were home! You really thought of everything for our comfort. Couple that with blue skies and 70 and 80 degree temperatures most of January and we were happy campers. Had great sunsets each night at the beach across the road and spent most mornings in the shade at Coquina Beach just a short car ride up to Bradenton Beach. The Blue Dolphin Cafe's breakfast and staff were great, as were lunches on the deck at the Hilton. The new Publix was a joy to shop in and I hate to shop! Longboat is a beautiful island...a real treasure of enjoyment. Thanks, again. The Huddlestons.

Keith Pearse

Keith Pearse



July 24, 2012

We just got back from a 3 week stay it was wonderful, wish we could of stayed longer. The apartment is lovely very clean and comfortable, it is a 2 minute walk to the beach which was so convenient. The beach is so nice we went for lots of walks and the sunsets are just amazing. Brad was very helpful and we will definitely book again. Thankyou for sharing your home with us. Kind regards the Pearse's.

Robert Lammers

Robert Lammers

Minster, OH

Three Months In Heaven

April 20, 2012

This villa absolutely lived up to its description and then some. It is well decorated, neat, and very, very clean. Being able to have a washer and dryer in the storage room outside kept noise at a minimum inside the unit. We ate our breakfasts in the tiled lanai with windows on three sides. It was like eating in the middle of a garden with all of the grass, bushes, flowers and a very Large fig tree for a focal point. Its one minute walk to the bay and three minutes to the white sand beach on the beautiful Gulf of Mexico. At the cluhouse, less than a minute walk away, thtere's a great swimming pool, fitness center library, men and women's sauna and a large meeting area for numerous social gatherings. There are many nice people at Windward Bay and we made a number of friends. W3ee madegood use of the furnished bikes, beach chairs and umbrella. You will not find more bang four your buck then thes villa. Bob and Dorothy



Mississauga, Ontario, Canada

Simply Awesome!

July 18, 2011

THE AREA: Longboat key and its surrounding area are gorgeous, it was our first visit to the area so we drove around many places, the area offers lots of possibilities in what to eat/do according to different personalities and budgets. THE BEACHES: This is the main reason to visit this place, there are beaches everywhere and they're all beautiful. THE VILLA: Very clean, safe and so convenient, everything is there for you to enjoy. THE OWNERS: Really straight up folks, they are a pleasure to deal with and they totally make the difference when booking a place for rent. My family and I had a great time here and hope to come back soon.

Brooks Basinger

Brooks Basinger

boston, ma and houston, tx

easy and relaxing!

April 25, 2011

I loved longboat key...and the condo provided everything my family needed. It is a short walk from the most lovely beach, where early morning swims and evening sunsets are spectacular. The sand is soft and white and the water and surf are clean and sooo swimable! The owners of the condo (Brad specifically) is super nice and he communicated with me clearly about all the details. That makes all the difference! They have two bikes and two pools and beach chairs and an umbrella! The clubhouse has a workout area (which we did not use) and a ping pong table (where we had a family tournament). We had a gas here and I would absolutely would return. We lucked out and not only had awesome weather, but we found a very comfortable place. The Basinger Family

Tony and Christine Martiano

Tony and Christine Martiano

toronto ontario canada

great vacation spot

August 10, 2010

We had a fantastic time at this location.The condo is very clean and has everything you need on a vacation.The kitchen was well stocked and we didn't even need to buy toilet paper, dishsoap etc. There are 2 bikes provided and we thoroughly enjoyed using the bike lane up and down the island.There is a company that delivered kayaks for the kids right to the property where you can directly access Sarasota Bay.Armands Circle is very impressive.This is a great location , so close to the beach and in a wonderful setting.There are quite a few delightful restaurants very nearby.The beach is stunning!All said we will definitely come again.Excellent value and well maintained by owners who were most accomodating.

Judy and John

Judy and John

Arlington, MA

New England escape!

April 12, 2010

Great beach access, very nice facilities (pools, library, tennis courts, work out area)and well equipped condo. Very reasonably priced. Highly attentive owners. We were just unlucky with the weather, March was the worst in recorded history of Florida!! Farmers' market, Owens Fish Camp, and sunset at the Hilton bar are terrific.




Fantastic spot

January 20, 2010

The beach is gorgeous the ground floor is so accessible. We enjoyed the ammenities, bikes, pool and beach what a month!

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Last updated: January 31, 2016

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Owner Profile

Brad Gabriel

Brad Gabriel

905 379 7433