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Longboat Key Florida Vacation Rentals - Home
1 / 44

Longboat Key Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 105 BR / 4.5 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$667

/ night

Email Owner
Bedrooms:5
Bathrooms:4.5
Sleeps:10
Type:Home
Per night:$667
Per week:$4,667
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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Longboat Key Florida Vacation Rentals - Townhouse
1 / 10

Longboat Key Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 73 BR / 3 BA / Sleeps 7
Townhouse / 3 Bedrooms / Sleeps 7

from

$267

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Townhouse
Per night:$267
Per week:$1,867
Pets allowed:No
Internet:Yes

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 noted architect Tim Seibert (Sarasota School of Design), this...

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1 / 49

Longboat Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 63 BR / 3 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$334

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$334
Per week:$2,334
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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Longboat Key Florida Vacation Rentals - Condo
1 / 8

Longboat Key Condo
1 Bedroom / 1 Bathroom / Sleeps 41 BR / 1 BA / Sleeps 4
Condo / 1 Bedroom / 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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Longboat Key Florida Vacation Rentals - Home
1 / 22

Longboat Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 63 BR / 2.5 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(2) Excellent 2 Reviews

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$229 - $429
Per week:$1,600 - $3,000
Pets allowed:Yes
Internet:Yes

Save 15% this May and June. $3400 for the month reduced from $4000. $1360 per week reduced from $1600 The Banyan home is ideally located just four blocks to the beach on the south end of Longboat Key in Country Club Shores. Situated on a large corner lot this spacious home has ...

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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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Longboat Key Florida Vacation Rentals - Condo
1 / 20

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4
(2) Excellent 2 Reviews

from

$59

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$59 - $184
Per week:$409 - $1,284
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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Beautiful, fabulous location.

“ Excellent ”
January 4, 2015
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 easy to follow.Except in Babados I have never seen so much attention paid to esthetics of the property, it was like being in a botanical garden. The condo itself had everything, we were able to cook a full CHRISTMAS dinner. Condo is beautifully decorated and the free calling and cable was a super bonus. The location makes trips to events everywhere in the keys easy and not travel intensive. Just around the corner (1.5 miles) from the new bay isles complex with a fabulous new publics and cvs. The beach is private and just across the road with umbrellas and plenty of chairs, and of course sensational sunsets. Mornings watching the sun rise on the bay was terrific I would not think twice about renting this condo again. Bravo Ravi!!!
Lee Easterly, Nova Scotia, canada

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Longboat Key Florida Vacation Rentals - Condo
1 / 10

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4
(10) Excellent 10 Reviews

from

$151

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$151 - $259
Per month:$4,530 - $7,770
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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...as we expected - nice!

“ Excellent ”
August 16, 2015
Netter, hilfreicher Vermieter, gute Ausstattung, schöne, ruhige, aussichtsreiche Anlage direkt am Meer. Das Büro sorgte sich nett um uns, trotz Anreise in der Nacht. Wir als Familie haben die Ferien hier in vollen Zügen genossen und kommen gerne wieder einmal. Ein tägliches Tennisspiel durfte nicht fehlen wie auch die ausgedehnten Strandspaziergänge oder Ausfahrten mit dem Bike. Strand übrigens sehr schön, sauber, nicht zu stark belegt (man will ja nicht alleine sein) und gut ausgestattet. Nette Grillstelle direkt am Meer - nun, ja, die Amis hatten die grösseren Steaks als wir...;) , anschliessend herrliche Sonnenuntergänge - einfach so wie erträumt. Und natürlich: Shopping!
hans-kaspar schwarzenbach, Zürich, Switzerland

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Longboat Key Florida Vacation Rentals - Condo
1 / 28

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6
(4) Excellent 4 Reviews

from

$139

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$139 - $319
Per month:$4,170 - $9,570
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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Great Place For your Vacation

“ Excellent ”
June 13, 2015
THIS WAS A GREAT CONDO UNIT NO 309 AND I WOULDN'T USE ANY OTHER IT WAS CLEAN, EXCELLENT FURNISHINGS AND ON THE 3RD FLOOR SO YOU ARE NOT OVERLOOKED THERE WAS EVERYTHING YOU COULD IMAGINE AND NOTHING LACKING IN THIS BEAUTIFUL UNIT ..I WOULD'NT STAY ANYWHERE ELSE THIS IS A GENUINE REPORT FROM MY WIFE AND MYSELF..LES C UK
Les Collinge, Cheshire U.K.

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Longboat Key Florida Vacation Rentals - Condo
1 / 11

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review

from

$176

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$176 - $515
Per week:$1,230 - $3,600
Pets allowed:No
Internet:Yes

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 cannot be beat! The beach is great and the pool and hot tub...

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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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Longboat Key Florida Vacation Rentals - Condo
1 / 23

Longboat Key Condo
3 Bedrooms / 2 Bathrooms / Sleeps 83 BR / 2 BA / Sleeps 8
Condo / 3 Bedrooms / Sleeps 8

from

$150

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$150 - $217
Per week:$1,050 - $1,517
Pets allowed:No
Internet:Yes

Our condo is a third floor unit, which we are currently renovating. It will be a fully furnished, 3 bedroom, (one king bed, two twin beds, one queen sofa bed, one full sofa bed) 2 bath condo with a lovely Gulf front view from the living room and balcony. You will have direct...

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Longboat Key Florida Vacation Rentals - Home
1 / 8

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(4) Excellent 4 Reviews

from

$125

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$125 - $150
Per week:$720 - $1,400
Pets allowed:No
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. Two minute walk...

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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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Longboat Key Florida Vacation Rentals - Home
1 / 13

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(1) Excellent 1 Review

from

$415

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$415 - $515
Per week:$2,900 - $3,600
Pets allowed:No
Internet:Yes

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 the perfect spot for relaxing days on the beach, followed by ...

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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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Longboat Key Florida Vacation Rentals - Condo
1 / 23

Longboat Key Condo
1 Bedroom / 1 Bathroom / Sleeps 41 BR / 1 BA / Sleeps 4
Condo / 1 Bedroom / Sleeps 4
(1) Excellent 1 Review

from

$99

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$99 - $190
Per month:$2,970 - $5,700
Pets allowed:No
Internet:Yes

We offer 2 relaxing, beautifully decorated 1 Bedroom / 1 Bath apartments 303 and 401 in the beautiful Beachcomber condo. See our unit's info on AwayToParadise Condo located right on the beach across the street from shopping malls with Pablix superstore, CVS, Italian restaurant...

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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 - Apartment
1 / 24

Longboat Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 52 BR / 2 BA / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

from

$135

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$135 - $238
Per month:$4,050 - $7,140
Pets allowed:No
Internet:Yes

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 in a great quality in every room, CD stereo system, Blu Ray ...

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Longboat Key Florida Vacation Rentals - Home
1 / 20

Longboat Key Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 62 BR / 2.5 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$300
Per week:$2,100
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 / 5

Longboat Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / 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 Florida Vacation Rentals - Condo
1 / 18

Longboat Key Condo
4 Bedrooms / 2.5 Bathrooms / Sleeps 104 BR / 2.5 BA / Sleeps 10
Condo / 4 Bedrooms / Sleeps 10
(23) Excellent 23 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 stay

“ Excellent ”
March 31, 2015
A wonderful Lbk place for a family vacation especially with kid/grandkid. Owner organization and communication was terrific
richard fiore, Illinois

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Longboat Key Florida Vacation Rentals - Condo
1 / 14

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4
(1) Excellent 1 Review

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$74 - $124
Per week:$514 - $864
Pets allowed:No
Internet:Yes

LOOKING FOR MED\LONG TERM RENTERS FOR 2016 May to December 2015 still available ... 1 month minimum Beautiful condo for rent.. third floor with elevator, Sunny corner unit Stunning view of the Gulf and the Bay. Very peaceful... Minimum Stay :1 month Kitchen well...

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Lovely condo - Excellent setting

“ Excellent ”
February 7, 2015
The condo is beautiful, with upgraded kitchen & bathrooms, charming furniture, and all the comforts of home. There are walk-in closets & plenty of drawer space to accommodate clothing for a longer stay. The are lovely water views from the living room of the Gulf of Mexico & of the Bay from the kitchen. The grounds & pool area are beautifully maintained & the walk to the beach is directly across the street. We walked & sat on the beach almost every day & went back in the evening to watch the glorious sunsets. The owner is kind, helpful if you need her & very accommodating. We highly recommend this condo & hope to return again.
Noelle & Paul Barton, South Bend, IN USA

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Longboat Key Florida Vacation Rentals - Condo
1 / 55

Longboat Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6
(8) Excellent 8 Reviews

from

$143

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$143 - $215
Per week:$1,000 - $1,500
Pets allowed:No
Internet:Yes

DECEMBER DEAL $3000/26 Nights 12/2- 12/26 + tax&fees. Booked until 7/31 PACK YOUR SWIMSUIT AND SMILE - THE REST IS HERE 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...

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It doesn't get better than this!

“ Excellent ”
April 7, 2015
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 beach towels, to books for a rainy day, to condiments in the fridge.. I particularly enjoyed walks on the beach and dips in the outdoor hot tub. Lots of great restaurants, interesting shops, museums, cultural events, an aquarium, etc. to enjoy. We felt more like we were borrowing a friend's condo than renting a vacation property. Hosts Ed and Nancy couldn't have been kinder or more helpful.
Marilee H. Garlanda, Sullivan County, New York

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Longboat Key Florida Vacation Rentals - Villa
1 / 25

Longboat Key Villa
1 Bedroom / 1 Bathroom / Sleeps 41 BR / 1 BA / Sleeps 4
Villa / 1 Bedroom / Sleeps 4
(13) Excellent 13 Reviews

from

$87

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Villa
Per night:$87 - $110
Per week:$607 - $770
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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Windward Bay Villa, Longboat Key FL

“ Excellent ”
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.
Bill Mattingly, Carmel, IN USA

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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 ...

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