Longboat Key Vacation Rentals, Condos, & More

1-21 of 21 Longboat Key Rentals

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Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$192

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$192
Per week:$1,342
Pets allowed:No
Internet:Yes

This condo rents for a minimum of 3 months at a time PER THE CONDO ASSOCIATION RULES (sorry we can not rent for any less of a timeframe). It is currently available Dec 19th through March 18th and January 5th through April 4th. Please let us know which dates you are interested in when...

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Longboat Key Florida Vacation Rentals - Home
1 / 44

Longboat Key Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 10

Bedrooms:5
Bathrooms:4.5
Sleeps:10
Type:Home
Per night:$1,000
Per week:$7,000
Pets allowed:No
Internet:Yes

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 corner, fully- equipped gourmet kitchen, fireplace, BBQ, and...

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Spacious double unit(walk to beach in offseason)
1 / 18

Longboat Key Condo
4 Bedrooms / 2.5 Bathrooms / Sleeps 10

“ Excellent ”22 Reviews

from

$195

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:10
Type:Condo
Per night:$195 - $225
Per month:$5,850 - $6,750
Pets allowed:Yes
Internet:No

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 towels. The walls are imbued with beach colors and themes, newer...

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Great home, Great beaches= Great Vacation

“ Excellent ”
October 18, 2014
I stayed with 5 of my girlfriends from college for our informal 30 year reunion and we loved it. There was lots of space to spread our wings but it was cozy with a wonderful full sized kitchen with an open family/living room to relax an socialize together. The home was bright, cheerful and clean and we were able to walk to the resort pool as well as to Euphemia Haye to enjoy their extroadinary desserts. We loved the key lime pie and likely gained 5 pounds in the process of indulging, but that's what vacations are all about! We are making plans to return again next year to the same residence. It actually exceeded all of our expectations as it cost less than many others we had considered on Longboat.
Sue Rodriuez, Chevy Chase ,MD

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Longboat Key Florida Vacation Rentals - Home
1 / 49

Longboat Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

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 architect Frank Folsom Smith, on property formerly owned by the ...

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View from balcony
1 / 13

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$150 - $197
Per week:$1,050 - $1,377
Pets allowed:No
Internet:Yes

This unit is only available on a monthly basis. This beautiful 2 bedroom, 2 bathroom unit is right on the water with gorgeous Gulf views from your own balcony. Walk right out to 10 miles of beach or enjoy a heated pool, boat dock, fishing pier and tennis courts. Beachfront Swimming...

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From Bay
1 / 7

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$77 - $150
Per week:$537 - $1,050
Pets allowed:No
Internet:Yes

Ground level unit in Banyan Bay Club - one of the most desirable on the key. Best of both worlds! Great views of Sarasota Bay, which lies just feet from your door AND just 200 yards to magnificent white sand private beach on Gulf of Mexico. See every sunrise and sunset without ...

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1 / 8

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$67 - $124
Per week:$467 - $864
Pets allowed:No
Internet:Yes

Looking for med/long term rental for 2016! ! ! ! ! ! Beautiful condo for rent.. third floor with elevator, corner unit Stunning view of the Gulf and the Bay. Very peaceful... Minimum Stay :1 month Kitchen well equipped with granite counters Breakfast area Nespresso...

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Island Paradise
1 / 16

Longboat Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$269

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$269 - $446
Per week:$1,880 - $3,120
Pets allowed:No
Internet:Yes

This canal front home with 3 Bedrooms, 2. 5 baths is immaculate and was renovated in 2004 with ceramic tile flooring throughout, wood kitchen cabinets, granite countertops, new appliances and with tremendous attention to detail. The furnishings are high quality with a modern,...

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Great house, with our own beach on the Gulf

“ Excellent ”
July 4, 2013
The house was great for our 1-week stay. Very comfortable, and couldn't ask for a better location.
Ed Berger, Rockville, MD USA

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sunset Gulf of Mexico
1 / 34

Longboat Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$74 - $107
Per week:$514 - $747
Pets allowed:No
Internet:Yes

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. This 27 acre condominium complex situated between the Gulf Of Mexico...

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Caught in a pickle

“ Excellent ”
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!!!
Dave Leaman, Waco Texas

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Outside of 843 bayport
1 / 20

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”1 Review

from

$50

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$50 - $167
Per week:$350 - $1,167
Pets allowed:No
Internet:Yes

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 serene and relaxing environment. 843 Bayport way is a 2 bedroom 2...

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EXCELLENT!!!!!!!!!!!!!!!

“ Excellent ”
June 11, 2014
EXCELLENT STAY AND BEAUTIFUL SURROUNDINGS
Dan Boston, LOUISVILLE, KENTUCKY

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Longboat Key Florida Vacation Rentals - Condo
1 / 10

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”6 Reviews

from

$165

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$165 - $181
Per month:$4,950 - $5,430
Pets allowed:No
Internet:Yes

== 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 on the exclusive island of Longboat Key. South facing balcony....

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Sandy Cay - unit 218

“ Excellent ”
June 15, 2014
I rented condo 218 together with my friend from Holland. We both have been to Longboat many times before but this was the best location ever. The building is nicely laid out, clean and efficient. The apartment was everything that was promised: excellent view of the gulf, rooms were clean and had all the amenities you would need. Specially loved the high chairs on the balcony !The complex provides beach chairs and in the apartment were sunbrella's and beach towels. So we had everything we needed. The beach was beautiful and we were lucky to see dolphins and lots of birds. And every day there was a new turtle nest !We didn't use the pool, but it looked nice and clean.Only (minor) issue was, that we wanted to stay a little longer on the last day, and the apartment wasn't rented after us. yet we had to pay $100 extra if we wanted to stay until 3 pm instead of 11 am. I find that rather steep.But overall we had a great time !
Arda van Dongen, Houston, Texas

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Longboat Key Florida Vacation Rentals - Condo
1 / 28

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$139

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$139 - $299
Per month:$4,170 - $8,970
Pets allowed:No
Internet:Yes

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...

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Gorgeous Condo

“ Excellent ”
November 1, 2013
We were fortunate to be able to spend a few days in Longboat Key for a mini-vacation of sorts and spent 3 nights in Unit 206 at Sand Cay. We were impressed by the beautiful décor of this newly-renovated condo on the second floor. I loved the layout and each room was beautifully decorated and gave a warm, cozy feeling throughout. There is a great view of the Gulf from the living area and balcony. The unit is equipped with everything one needs for a fun, relaxing vacation. We will definitely recommend this to friends and family and hope to return for a longer stay!
Colleen Moore Mauk, Marion, OH

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Longboat Key Florida Vacation Rentals - Condo
1 / 11

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$285

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$285 - $500
Per week:$1,995 - $3,495
Pets allowed:No
Internet:Yes

This deluxe beachfront unit was updated in 2012 with new living room furniture including a 55" flat screen television. Many upgrades fall 2010 include new flooring, kitchen appliances, beautiful kitchen counters and fresh interior paint. The perfect island getaway, located on the...

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Longboat Key 3007

“ Excellent ”
July 24, 2012
The apartment was beautifully furnished and the kitchen was well equipped. The view from the balcony - the apartment was on the tenth floor - was spectacular. The only downside to the interior was that the bathrooms were quite small and old, and there were no ceiling fans, which made the bedroom quite stuffy. (There was a floor fan but this was very noisy.)The beach area was lovely and as we on a resort loungers and sun umbrellas were available. Because we visited in July, the beaches were very quiet. St Armand's Circle, which was very close, was busy but it was never a problem finding a place to eat, the shops were charming and we enjoyed window shopping. Our main complaint, is that the apartment was part of a resort but we were not. To explain, we were allowed to use the beach and the pool as well as the loungers and umbrellas, but everything else, towels, cabanas, food, and drinks - which were served on the beach and poolside - as well as the bar and restaurant were by resort card only and we were not allowed to have a resort card or use a credit card. In retrospect, it wasn't a bad thing as we ate more healthily and didn't drink a lot of extra calories!All in all it was a wonderful, relaxing week, we probably wouldn't use the apartment again but that's because we like to try new destinations.
Rowena Croxford, Chicago, IL USA

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Step across wooden walkway to our private beach & warm gentle azure gulf waters
1 / 55

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”7 Reviews

from

$117

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$117 - $217
Per week:$817 - $1,517
Pets allowed:No
Internet:Yes

PACK YOUR SWIMSUIT AND SMILE - THE REST IS HERE (BOOKED UNTIL 4/29/) Take the wooden walkway to swim in warm gentle azure gulf waters Walk softly past sea turtle nests & shell on your own private gulf beach Watch dolphins & shore birds from sun umbrellas & loungers set up ...

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Great location; beautiful beaches; awesome owner

“ Excellent ”
November 26, 2014
Club Longboat is a wonderful development with excellent property managers. I stayed at Ed's condo from August thru October of 2014. Even during the 'low season', this area is just plain awesome. The beaches, pools, and fitness facilities are excellent. The grounds are well kept, safe, and inviting. Ed was outstanding to work with and really went the extra mile to make sure my stay was first rate. The condo is very spacious, well appointed, and very comfortable. It has nice views and everything you could possibly need. The Internet connection is reliable and fast if you need online access. Longboat Key is undoubtably the best gulf island in the area and Club Longboat is one of the nicest communities on the island. I highly recommend this property and owner!
James Kimmerle, Indianapolis, IN

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Longboat Key Florida Vacation Rentals - Condo
1 / 22

Longboat Key Condo
Studio / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$135

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$135 - $190
Per week:$912 - $1,470
Pets allowed:No
Internet:Yes

Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every evening,...

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Nice Room

“ Excellent ”
September 3, 2014
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 way to the beach at night.
Bill Ashby, Florida, usa

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Longboat Key Florida Vacation Rentals - Home
1 / 13

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$458

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$458 - $600
Per week:$3,200 - $4,200
Pets allowed:No
Internet:Yes

BEACHFRONT CHRISTMAS SPECIAL - SAVE 15%. $2, 550 FOR THE WEEK REDUCED FROM $3, 000. JANUARY 30% OFF - $2, 520 PER WEEK REDUCED FROM $3, 600. This casual beach home is just the right place to enjoy a laid- back, toes- in- the- sand vacation! Nestled on the shores of...

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Loved It!!

“ Excellent ”
October 16, 2014
We spent a week at this property & absolutely loved it. Even our kids (ages 21 & 25) were saying best time ever. We had planned to do a couple day trips to the Orlando area and only ended up leaving the area once (to Universal) because no one wanted to waste a day somewhere else! The beach was awesome for shelling. The dolphins made a swim by everyday. The fishing was awesome. My husband had no problem setting an alarm for 6 a.m. so he could start his fishing days early. As for me, the pool was a small slice of heaven. We didn't use the pool table (needed work), or the table tennis (needed paddles), or the bikes (only 1 worked) but with a pool & your own beach who wanted to be inside...No One LOL!! The house itself is older but with an unique character & charm that fits perfectly with a beach escape. The kitchen was well stocked with all the things we needed. Cooked the fish we caught & life was good! If you want a true private beach experience this is the place! :)
Donna Needham, Nebraska

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1 / 8

Longboat Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$84

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$84
Per week:$584
Pets allowed:No
Internet:Yes

Wonderful gulf front one bedroom one bath fully furnished condo with king bed and two sofas for sleeping. Expansive white sandy beach. Private walled garden in back of screened porch and patio and living room, dining room and kitchen face the patio, pool and view of the gulf with...

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1 / 8

Longboat Key Villa
1 Bedroom / 1 Bathroom / Sleeps 4

from

$84

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Villa
Per night:$84 - $97
Per week:$584 - $677
Pets allowed:No
Internet:Yes

Make this charming Beach Villa your seasonal escape! ! 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 nestled between the Gulf Of Mexico and the Bay offers a...

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Longboat Key Florida Vacation Rentals - Home
1 / 22

Longboat Key Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

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 bedrooms, an outside sleeping porch/bunk bed, along with 2...

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A new adventure

“ Excellent ”
December 4, 2014
We rented a boat for the week. The owner met us at the marina and guided us to the island. Very hospitable. When we arrived the music was playing and it was quite magical. Wonderful retreat for my family. We were there to celebrate a few birthdays and Thanksgiving. Great table for 12 people to comfortably sit around as there were many places to sit and enjoy a fire, the view and the sunset. The dock was also a great place to hang out. We all really enjoyed this new adventure and would highly recommend.
Valerie Sloan de Stefanis, CT

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Longboat Key Florida Vacation Rentals - Home
1 / 8

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”4 Reviews

from

$125

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$125
Per week:$720 - $1,360
Pets allowed:Yes
Internet:No

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 area. Quiet upscale residential neighborhood. Three minute...

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Great Place to Stay!

“ Excellent ”
June 10, 2014
This was a great vacation home rental at a great price. The home was very clean and very roomy. We have four children and they all enjoyed it very much! The pool has a toddler gate which is wonderful option as we have a 2 yr old. I would highly recommend this property. It is about 15 minute drive to a public beach, but worth the drive to stay in this quiet, peaceful neighborhood, away from the beach noise and traffic. We will definitely be looking at this house as an option if we return to the area next year!
Lisa Duncan, Indianapolis, IN

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Home on Canal/ 5 minute walk to Beach
1 / 5

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$127

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$127
Per week:$887
Pets allowed:Yes
Internet:Yes

House on canal, 5 minute walk to the Beach. A 3bedroom/ 2 bathroom home on the north end of Longboat Key, Florida. One king bed, 2 Queen beds, and One bath has a walk- in shower and the other has the tub choice. A nice large kitchen to cook for your family and friends, while...

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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. When making your family travel plans, call ahead and schedule visits to attractions in advance whenever possible. Many Florida attractions offer family packs at a discount that include fun for all ages.
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 near vacation rental by owner homes. 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
When you go online to reserve your Longboat Key vacation rental early, you have your choice of home from a wide selection of Longboat Key condo rentals located within a short drive to local beach access. Early reservations also mean you have a choice of a Longboat Key house rental that offers all the comforts of home while allowing you to enjoy local dining and other 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. When you stay in any Longboat Key rentals you are ideally based for a fun trip to the park without a long commute.
Blind Pass Beach
Blind Pass Beach may be one of the best kept secrets in the Longboat Key area. Located approximately 12 miles from many Longboat Key vacation rentals 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 any of the ideal vacation rentals Longboat Key has to offer 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!
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