Longboat Key Vacation Rentals & Apartments - 28 Rentals Available

Sort: Relevance
Min price
Max price
More filters
Your search has been expanded to include more rentals
Close x
1 / 44

Longboat Key Home
5 BR / 4.5 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 4.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"Fabulous home located beach front. House was everything as advertised. Kitchen very well equipped. Property manager responded very quickly to the few issues we had while there. Very Impressed."
- Don Bereheiko, Brigantine, NJ
(2) Excellent (2 reviews)
1 / 49

Longboat Key Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Our Stay at the Conrad Cabana on Longboat Key was more than we had wished for. The moment we entered the home we knew that we would be very comfortable and we were. Throughout the rental process everything went smoothly and when we arrived we were met..."
- Brenda Shapiro, Las Vegas, Nevada and Indianapolis, Indiana
(1) Excellent (1 review)
1 / 18

Longboat Key Condo
4 BR / 2.5 BA / Sleeps 10 4 10 Min stay varies
Condo / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"We rented this for our women's group over the first weekend in November. It was spacious, well kept, and nicely located on Longboat Key. Our ladies absolutely loved the time we spent here, and the memories we were able to make. Can't wait to do it ..."
- Emily Hamsher, Englewood, FL
(25) Excellent (25 reviews)
1 / 10

Longboat Key Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Saubere, sehr gut ausgestattete und geschmackvoll eingerichtete Wohnung mit allem was man benötigt und noch vielem mehr. Im 2. Stock (= 3rd Floor in USA) gelegen, über eine Außentreppe direkt neben dem zur Wohnung gehörenden Parkplatz oder per ..."
- Dirk Jendritzki, Germany
(11) Excellent (11 reviews)
1 / 25

Longboat Key Condo
2 BR / 2 BA / Sleeps 4 2 4 30 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The condo is much larger and much more upscale then the pictures actually show. The location on the resort site makes for an excellent vacation, no noise, close to pool and fitness Center. The direction left by the owner re everything was exact and ..."
- Lee Easterly, Nova Scotia, canada
(2) Excellent (2 reviews)
1 / 20

Longboat Key Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The Longboat Beach Club was a beautiful vacation location! The hotel room was the best I ever had. The beach was picture perfect, the food was excellent and the weather could not have been better. I thought I was vacationing in heaven! Thank you!..."
- Lisa Gilbert, Indianapolis. Indiana
(2) Excellent (2 reviews)
1 / 24

Longboat Key Condo
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Room was very clean and nicely updated, The air systems worked great and were quiet. great access to beach with a nice pool. The only thing I did not like was that there is no lighting in the outside hall ways and pool area. total darkness to make your..."
- Bill Ashby, Florida, usa
(1) Excellent (1 review)
1 / 24

Longboat Key Apartment
2 BR / 2 BA / Sleeps 5 2 5 5 night min stay
Apartment / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"This was our first time to Longboat Key, Florida. This condo was adorable and in a great location! We arrived at night and once we unlocked the door were so relieved. It is a quaint 2 bedroom 1 bath condo that was so clean and lovely furnishings. We..."
- Cassy Landreth Maher, Holland, Michigan USA
(1) Excellent (1 review)
1 / 8

Longboat Key Home
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Air Conditioning
"I would highly recommend. Very clean and comfortable- great floor plan. We enjoyed our breakfast and evenings in the lanai daily! About 100 yards walk to clean, beautiful beach."
- Justine Carter, New Haven CT
(7) Excellent (7 reviews)
1 / 27

Longboat Key Villa
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Villa / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"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..."
- Dave Leaman, Waco Texas
(13) Excellent (13 reviews)
1 / 55

Longboat Key Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The two balconies and lanai overlooking the fabulous Gulf of Mexico provid a beautiful and ever- changing view of Nature's best work. Condo is large, clean and comfortably furnished with wifi and 3 TV's. Every convenience has been thought of, from ..."
- Marilee H. Garlanda, Sullivan County, New York
(8) Excellent (8 reviews)

About Longboat Key

With endless white sand beaches and unobstructed views of the Gulf of Mexico, it’s no surprise that Longboat Key is a vacation hotspot. Book the perfect seaside Longboat Key condos for you and your family, and get ready for a vacation you won’t forget.

Introduction to Longboat Key

Located just off the Gulf Coast of Florida, Longboat Key is a barrier island that includes just four square miles of land and about 12 square miles of water. With such an expansive waterfront, Longboat Key is a true beach community. Many residents live here only in the winter, which means there are numerous vacation homes available throughout the warmer months.

Longboat Key Climate

Like many Gulf Coast communities, Longboat Key welcomes hot, humid summers and warm winters. The highs in July and August average about 90 degrees, while December and January days typically top out around 60 degrees. Longboat Key welcomes over 250 sunny days, and though the area receives an above average amount of rain, it’s extremely rare to spot snow along the coast.

How to Get Around Longboat Key

West Florida is a car lover’s paradise, with Gulf of Mexico Drive as the single main road that extends along the length of the key. Most Longboat Key condos are just a short drive away from both the main drag and the waterfront, so be sure to rent a car if you’re flying into Sarasota Bradenton International Airport.

Hit the Beaches

Longboat Key Beach faces the Gulf of Mexico and boasts clear, calm water and soft, white sand. You won’t find buzzing boardwalks or massive crowds here, but you will find plenty of space to swim and sunbathe. There are several public beach access points along the key, but arrive early to take advantage of limited parking.
At the northern edge of the key, Beer Can Island offers a secluded spot to swim, fish, and gather with friends. Since this beach is only accessible by boat, plan to rent a boat or charter a boat trip.

Explore the Gulf

One of the most popular ways to explore offshore is renting a boat. Outfitters like Cannons Marina and CB’s Saltwater Outfitters rent boats by the half day, full day, or week. Depending on what you want to do and the size of your group, you can rent a three-person motorboat for fishing, a six-person speedboat for cruising along the coast, or a 14-person pontoon that’s perfect for spending the day at sea. Be sure your group’s driver has a driver’s license and some boating experience under his or her belt.

Go Golfing

If you're a landlubber, rest assured there's plenty to do back on shore. Harbourside Course offers three different courses and 27 holes of golf. Play in the midst of flora like palmettos and palms, and enjoy the sparkling gulf views and refreshing breeze.

With easy beach access, activities on and offshore, and numerous Longboat Key condos for rent, this spot makes the perfect beach vacation.


Longboat Key Travel Tips

If you are looking for a vacation destination that includes white sandy beaches and a great mix of activities for the whole family to enjoy, make plans now to visit Longboat Key, FL. With the Gulf of Mexico on one side and Sarasota Bay on the other, there are miles of beach to be explored. The neighboring attractions in Sarasota, Bradenton, and Anna Maria Island offer more opportunity to explore the area while enjoying the Caribbean-like beaches of Longboat Key. Plan your family vacation today with VacationHomeRentals.com and enjoy your visit from any of the many Longboat Key rentals on the island. 

Longboat Key Attractions

While it is no secret that the main attraction of Longboat Key is the easy access to many popular beaches, you can find many family centered adventures within nearby parks. Longboat Key offers plenty of opportunities to enjoy first class shopping and dining. Continental cuisine, fresh seafood, coffeehouses, and more are all available. Enjoy shopping at Longboat Key's Avenue of Flowers shopping area, the specialty boutiques at The Centre Shops or explore the galleries and shops at St. Armand Circle. If you are a collector of beautiful antiques you will want to be sure and visit the Soma District, located a short drive from Longboat Key.
The entire island is only 11 miles long but includes easy access to some of the most beautiful beaches in the state. While it may be hard to decide on a favorite beach during your first visit, you can find Longboat Key vacation rentals to choose from that provide you with the ideal starting point for access to one or several of the following beaches.
  • Greer Island
  • Cortez Beach
  • Holmes Beach
  • Manatee County Beach
  • Ann Marie Beach
  • Coquina Beach
  • Lido Key
Enjoy local dining and attractions such as these:

South Lido Park

South Lido Park a beautiful park covers 100 acres and offers attractive views of the Gulf of Mexico and the city of Sarasota. The whole family will enjoy kayaking, picnics, cookouts, nature trails, and many more seasonal outdoor activities. 

Blind Pass Beach

Blind Pass Beach may be one of the best kept secrets in the Longboat Key area. Located approximately 12 miles from Longboat Key this beach is a bit isolated, but offers the seclusion you might expect to find on a Caribbean vacation! Plan a day to enjoy the water, free parking, playground equipment to keep the younger family members busy and much more. You and your family can wander along the nature trail that includes dunes, rent a canoe or kayak to launch from the beach, or try your luck at fishing.
Other attractions you and your family may enjoy while relaxing in Longboat Key include Quick Point Nature Preserve and Islandside Golf Club. Additionally, you and your family are sure to enjoy are the Chartered Fish Tours and Ringling Bros. Barnum & Bailey Circus. The circus winter headquarters are in Bradenton which is a short drive from Longboat Key. Kids and adults alike will enjoy a tour of the museum and an opportunity to tour the grounds and enjoy regularly scheduled shows and exhibits.

Longboat Key Events

As a small town, Longboat key doesn't have a lot of events aside from their annual Holiday Night of Lights which features Christmas carol sing-alongs and a parade, but neighboring cities such as Bradenton provide ample entertainment and opportunities. Every Sunday you can enjoy Jazz Brunch on the Beach in Anna Maria. On New Year's Eve, a big celebration happens on Main Street in Bradenton.
Plan your family vacation travel today with VacationHomeRentals.com and see for yourself why so many families like yours return to Longboat Key every year!