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Longboat Key Florida Vacation Rentals - Condo
1 / 18

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
Welcome to our Groundfloor Beachfront condo! From large living and dining area with open kitchen just step outside to your patio with privacy and walk right out to the BEACH! Magnificent condo 1100 sqft with open f...
Longboat Key Florida Vacation Rentals - Home
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
This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every cor...
(2) Excellent (2 reviews)
Longboat Key Florida Vacation Rentals - Condo
1 / 22

Longboat Key Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
We have two beautiful condos at Club Longboat. One is a beachfront condo and the other is a garden unit with a restricted view of the Gulf of Mexico from the living room balcony. Both condos are fully furnished, three b...
Longboat Key Florida Vacation Rentals - Home
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
Located near the historic town of Longboat at the north end of Longboat Key, this Key West- style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed arch...
(1) Excellent (1 review)
Longboat Key Florida Vacation Rentals - Condo
1 / 28

Longboat Key Condo
2 BR / 2 BA / Sleeps 6 2 6 30 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
One Month Minimum Rentals Only. No Weekly Rentals. One Of Longboat Key's Best Kept Secrets! Longbeach Is Located At The North End Of The Island, Right On The Gulf Of Mexico. This Quiet Community Offers A Pool And T...
(2) Excellent (2 reviews)
Longboat Key Florida Vacation Rentals - Home
1 / 17

Longboat Key Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
ONE WEEK MINIMUM RENTAL HOME This casual beach home is just the right place to enjoy a laid- back, toes- in- the- sand vacation! Nestled on the shores of the Gulf of Mexico at the north end of Longboat Key, it's t...
(1) Excellent (1 review)
Longboat Key Florida Vacation Rentals - Condo
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
Minimum 30 Day Rental Longboat key offers uncrowded beaches, great food and serene accommodations. Bayport Beach and Tennis Club is a beach to bay complex made up of 2 story buildings that offer privacy in a very sere...
(2) Excellent (2 reviews)
Longboat Key Florida Vacation Rentals - Condo
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
== Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort...
(10) Excellent (10 reviews)
Longboat Key Florida Vacation Rentals - Condo
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 perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52' long, open beachfront lanai. The views c...
(2) Excellent (2 reviews)
Longboat Key Florida Vacation Rentals - Apartment
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
Perfect holiday apartment that is continually renovated. Building was completely renewed in 2008. With 103 sq. m. and balcony, accommodation for up to 5. With all imaginable furnishing, e. g. full HD TV, free Pay TV i...
(1) Excellent (1 review)
Longboat Key Florida Vacation Rentals - Villa
1 / 25

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
Conde Nast Voted Longboat Key The Second Best Island Destination In North America Located On Fabulous Longboat Key Approximately 3 Miles South Of Anna Maria Island, 6 Miles North Of Armand's Circle At Windward Bay. Th...
(13) Excellent (13 reviews)
Longboat Key Florida Vacation Rentals - Condo
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
Beautiful 3000 square foot freestanding condo home in tropical Cedars Tennis Resort, situated across the street from the white sands of the Gulf of Mexico. Recently updated with new linens, pillows, and quick- dry tow...
(24) Excellent (24 reviews)
Longboat Key Florida Vacation Rentals - Townhouse
1 / 26

Longboat Key Townhouse
2 BR / 1.5 BA / Sleeps 4 2 4 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
'Very Welcoming & Peaceful' - several times quoted from our Guests Book. Best value on Longboat Key... Longboat Key is one of the most beautiful and secure barrier islands off of the west coast of Florida. Our townh...
Longboat Key Florida Vacation Rentals - Townhouse
1 / 10

Longboat Key Townhouse
3 BR / 3 BA / Sleeps 7 3 7 90 night min stay
Townhouse / 3 Bedrooms / Sleeps 7
3 bedrooms 3 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
A special address on the Gulf of Mexico beach at the very north end of Longboat Key overlooking a bird sanctuary with views of the sea, sky and our extraordinary sunsets. One of nine contemporary townhomes designed by n...
Longboat Key Florida Vacation Rentals - Apartment
1 / 17

Longboat Key Apartment
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Apartment / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Being steps away from the longest stretch of private beach on Longboat Key and 30 acres o...
Longboat Key Florida Vacation Rentals - Home
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 • Washer/Dryer
Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining a...
(4) Excellent (4 reviews)
Longboat Key Florida Vacation Rentals - Condo
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
Couples Special 12/1 - 1/30 $8000/60 Nites + Tax & Fees Pack Your Swim Suit & Smile - The Rest Is Here Take The Wooden Walkway To Swim In Warm Gentle Azure Gulf Waters Walk Softly Past Sa Turtle Nests & Shell O...
(8) Excellent (8 reviews)
Longboat Key Florida Vacation Rentals - Home
1 / 20

Longboat Key Home
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2...
(1) Excellent (1 review)
Longboat Key Florida Vacation Rentals - Condo
1 / 23

Longboat Key Condo
1 BR / 1 BA / Sleeps 4 1 4 No min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
We offer two beautiful completely renovated in September 2015 1 Bedroom / 1 Bath apartment in the Beachcomber condo. Unit 303 and 401. See our unit's info on AwayToParadise Condo located right on the beach across th...
(1) Excellent (1 review)
Sarasota Florida Vacation Rentals - Home
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Sarasota Home - 4.0 mi away
3 BR / 2 BA / Sleeps 5 3 5 7 night min stay
Home / 3 Bedrooms / Sleeps 5
3 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
Sarasota Florida great beaches, nice gulf area - on the West coast of FL... perfect fun- filled getaway! FREE Beach parking! ! ! Amazing Sunsets! ! ! Summer Savings! ! ! Spring & Fall Specials Relaxing...
(14) Excellent (14 reviews)
Sarasota Florida Vacation Rentals - Guesthouse
1 / 11

Sarasota Guesthouse - 4.2 mi away
1 BR / 2 BA / Sleeps 3 1 3 Min stay varies
Guesthouse / 1 Bedroom / Sleeps 3
1 bedrooms 2 bathrooms Sleeps 3
High Speed Internet • Microwave • Washer/Dryer
Newly remodeled 'Old Florida' Guest Cottage is a charming vacation rental destination located half a block from Sarasota Bay on a one block street, west of the Trail. A well equipped, fully applianced eat- in kitchen, ...
(10) Excellent (10 reviews)
Beach house at St. Armand\\\'s Key
1 / 17

Sarasota Home - 4.4 mi away
3 BR / 2 BA / Sleeps 7 3 7 7 night min stay
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
Historic Florida home has been architectually designed to reflect the essence of St. Armands Key's "Old World Charm". Steps away from the world- famous St. Armands Circle with dozens of highly rated restaurants, upscale...
(6) Excellent (6 reviews)
Sarasota Florida Vacation Rentals - Condo
1 / 8

Sarasota Condo - 4.4 mi away
Studio / 1 BA / Sleeps 2 0 2 Min stay varies
Condo / Studio / Sleeps 2
Studio 1 bathroom Sleeps 2
High Speed Internet • Microwave • Air Conditioning
King Size Bed, Condo Room - 350 Sq Ft, 1 Bath Privately Owned - Independently Operated Condominium Located In A Hotel At 7150 N Tamiami Trail, Sarasota... With: Direct Water Views Of The Sara Bay Marina. 1 Bedroo...
Sarasota Florida Vacation Rentals - Condo
1 / 8

Sarasota Condo - 4.4 mi away
Studio / 1 BA / Sleeps 2 0 2 Min stay varies
Condo / Studio / Sleeps 2
Studio 1 bathroom Sleeps 2
High Speed Internet • Dishwasher • Microwave
New king size bed with new 47 inch led flat screen television with full cable and HBO. Full bathroom with bath/shower. Microwave and small refrigerator.
Sarasota Florida Vacation Rentals - Condo
1 / 16

Sarasota Condo - 4.4 mi away
2 BR / 2 BA / Sleeps 8 2 8 No min stay
Condo / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Air Conditioning
Please Email Me For A Link To Preferred Listing Address This Is A Privately Owned Condominium At 7150 N Tamiami Trail, Sarasota, Directly On The Sara Bay Marina With Direct Access To The Gulf Of Mexico. Yacht Rentals ...
(2) Excellent (2 reviews)
Bradenton Florida Vacation Rentals - Condo
1 / 16

Bradenton Condo - 4.6 mi away
2 BR / 2 BA / Sleeps 4 2 4 90 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
Dishwasher • Microwave • Washer/Dryer
First floor in four story building with elevator. Split floor plan with bedroom and bath on each side of living room. Large screen porch off living room and both bedrooms. Nicely appointed. Coin operated washers and drye...
(2) Excellent (2 reviews)
Sarasota Florida Vacation Rentals - Home
1 / 13

Sarasota Home - 4.6 mi away
2 BR / 1.5 BA / Sleeps 2 2 2 7 night min stay
Home / 2 Bedrooms / Sleeps 2
2 bedrooms 1.5 bathrooms Sleeps 2
High Speed Internet • Microwave • Washer/Dryer
2 bedroom, 1. 5 bath home with a sunroom/office on a large private property in a highly desirable residential neighborhood in the Indian Beach Sapphire Shores/ Ringling Museum area. Lovely, bright, with an open floor ...
Bradenton Florida Vacation Rentals - Condo
1 / 21

Bradenton Condo - 4.7 mi away
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
(Before sending an inquiry please see minimum # nights for period requested). Elegant condo on the IMG golf course. March 2015: all new furniture, new paint, new linens. September 2015: new kitchen, bathrooms and ...
(1) Excellent (1 review)
Sarasota Florida Vacation Rentals - Guesthouse
1 / 10

Sarasota Guesthouse - 4.7 mi away
1 BR / 1 BA / Sleeps 2 1 2 7 night min stay
Guesthouse / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Dishwasher • Microwave
Be swept away to luxurious Spain in this beautiful one bedroom guesthouse overlooking a lovely pool. Relax and sip your morning coffee as you take in the peaceful surroundings and bay breezes, with a private entrance, ...
(28) Excellent (28 reviews)
Sarasota Florida Vacation Rentals - Condo
1 / 8

Sarasota Condo - 4.9 mi away
1 BR / 1 BA / Sleeps 4 1 4 30 night min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Please Check The Availability Calendar Before You Email Us. Sorry, We Cannot Do Short Term Rentals Due To Condo Regulations! The Rustle Of Palms And A Gulf View! We're Across The Street From The Sands Of Lido Beach, ...
(2) Excellent (2 reviews)
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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.

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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!