Longboat Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Longboat Key, Florida on RentalSaver.com!

Longboat Key Rentals

From $420 per night (USD)
VRBO
Sea Grape Inn #7 - Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 1-Queen, 1-Sofa Sleeper ** Ne ...
From $420 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Sea Grape Inn #5- Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...
From $420 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Sea Grape Inn #4- Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen. ** Need to stay less ...
From $439 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Luxury Condo located on Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
. The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along w ...
From $317 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Spectacular 5-star Condo. Walk to beach & restaurants. Just remodeled.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, restaurants, groceries and more. Perfect pla ...
From $185 per night (USD)
VRBO
$4 BR\/3 BA Lido Canal Home by FVC$
From $1024 per night (USD)
VRBO
4 BR\/3 BA Lido Canal Home by FVC
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Offered by FL Vacation Connection, Kon-Tiki is a 4 brm + den private pool home with dock. Contemporary coastal décor wi ...
From $1024 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Whitney Beach Gulfside With Balcony! 30 day lease but real occupancy negotiable.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
All the comforts of home in this one bedroom, one bathroom condo with killer views. Located on Whitney Beach, this condo ...
From $198 per night (USD)
VRBO
$May 2024 available! Condo on the beach, Sunset view, Monthly rental 2B\/B2, Pool$
From $264 per night (USD)
Expedia
May 2024 available! Condo on the beach, Sunset view, Monthly rental 2B\/B2, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor ...
From $264 per night (USD)
Expedia
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VRBO
On the Beach - 1 week rental Long Boat Key ( Sarasota barrier Island )
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
June 29 thru July 6 this is week 26 ONLY Week 26 & 27- UNIT 402 are both available, discount if you book both wee ...
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VRBO
From $158 per night (USD)
Expedia
Luxurious Beachfront Villa with Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secl ...
From $158 per night (USD)
Expedia
From $244 per night (USD)
VRBO
LBK Getaway
Bedrooms:
4
Bathrooms:
2
Sleeps:
5
Welcome to Paradise at LBK Getaway! Great opportunity to stay at an exquisite 2-bedroom, 2-bathroom villa style home in ...
From $244 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Beachcomber unit 401
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $265 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Million Dollar View!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy what I call my ‘Million Dollar View’ of the turquoise Gulf of Mexico ocean and sugar white sand from this amazing ...
From $250 per night (USD)
VRBO
From $159 per night (USD)
Expedia
1st Floor Home Away from Home - Steps to Beach - Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A very warm welcome to your beautiful, home away from home on this Island Paradise! This gorgeous location is truly on ...
From $159 per night (USD)
Expedia
From $334 per night (USD)
VRBO
A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Beachfront cottage that is located directly on the Gulf of Mexico and the only thing that is between you and your beach ...
From $334 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Gulf-Front - Anna Maria Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Full Gulf-Front Condominium in well maintained complex. Secured building and covered parking (1 space). Beautiful pool, ...
From $325 per night (USD)
VRBO
$Beautiful Longboat Key RESORT 2 bed\/2 bath, Sleeps 6,Granite\/Stainless Kitchen$
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VRBO
Beautiful Longboat Key RESORT 2 bed\/2 bath, Sleeps 6,Granite\/Stainless Kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Bay Club provides vacation accommodations that include recreation and pampered relaxation. Take advantage of th ...
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VRBO
From $276 per night (USD)
Expedia
Gulf Getaway with Porch + Direct Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in th ...
From $276 per night (USD)
Expedia
From $488 per night (USD)
VRBO
2 bedroom beachfront condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a bea ...
From $488 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Cozy Vacation Spot Just minutes away from St Armands Circle
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Two bedroom paradise escape just off St Armands Circle in beautiful Sarasota FL. You will be a 2-minute walk from a va ...
From $239 per night (USD)
VRBO
From $379 per night (USD)
VRBO
Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is on ...
From $379 per night (USD)
VRBO
From $825 per night (USD)
Expedia
Paradise awaits at this sparkling 7 bedroom luxury home with pool & rooftop deck
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
Crystal Waves Oasis by Anna Maria Island Locals Home in Bradenton Beach, FL Features: • Private Pool and Spa • Rooftop ...
From $825 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two minute walk to Private Gulf Beach access, no need to cross the street. This charming unit is the only 2 bedroom gro ...
From $249 per night (USD)
VRBO
$GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH$
From $412 per night (USD)
Expedia
GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key! Magnific ...
From $412 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Welcome to your Beach Front Dream Condo! LBKTP102
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
BOOK NOW! AVAILABLE FOR DECEMBER 2023 FOR $ 8500 PER MONTH AND JANUARY 2024 FOR $8500 PER MONTH! Gulf Front Longboat Key ...
From $258 per night (USD)
VRBO
From $315 per night (USD)
VRBO
UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS PROPERTY HAS BEEN INSPECTED BY AND REGISTERED WITH THE TOWN OF LONGBOAT KEY RRR# 00134.2023 *****ONLY ONE RENTAL ...
From $315 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Spacious 2Bdrm Longboat Key Condo
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Paradise awaits in this beautiful 2 bedroom/2.5 bath condo in the heart of Longboat Key. Conveniently located near Sara ...
From $289 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Florida's Longboat Key Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
MINIMUM RENTAL ONE WEEK: MARCH 9, 2024- MARCH 16, 2024 MARCH 16, 2024-MARCH 23, 2024 The Veranda Beach Club on Lon ...
From $500 per night (USD)
Expedia
From $209 per night (USD)
VRBO
UNIQUE LONGBOAT KEY OASIS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We are please to offer our lovely, artfully ornamented and spacious 2BR/2BA second floor unit on a Longboat Key. Functio ...
From $209 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Cedars East #519 Townhome by RVA
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...
From $247 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Peaceful Longboat Key Canal Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat dock ...
From $177 per night (USD)
VRBO
From $123 per night (USD)
Expedia
Whitney Beach #336 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with ne ...
From $123 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Beach Front Condo Newly Renovated
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Longboat Key second floor beach-front condo, with two bedrooms, additional bonus room, two full bathrooms, breathtaking ...
From $226 per night (USD)
VRBO
From $212 per night (USD)
VRBO
Longboat Key Club!! Direct Beachfront!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming poo ...
From $212 per night (USD)
VRBO
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VRBO
Silver Sands, Oceanfront - Gulf Beach Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
55 steps away from the Gulf of Mexico Beach! Beautiful beach with the most amazing sunsets. Family friendly resort wit ...
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VRBO
From $875 per night (USD)
VRBO
Luxury 4 brm home by FVC
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to one of the most picturesque views on Longboat Key. Elegance, privacy and nature abound in this stunning Long ...
From $875 per night (USD)
VRBO
$BEAUTIFUL VIEWS OF THE BAY! THIS IS AN AMAZING 2\/2!$
From $311 per night (USD)
VRBO
BEAUTIFUL VIEWS OF THE BAY! THIS IS AN AMAZING 2\/2!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Want a beautiful view of the Sarasota Bay from a luxury condo on Longboat Key? This two bedroom second Floor unit with T ...
From $311 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Love the beach? Tennis? Swimming? This great family friendly retreat has it all!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Spacious 2400 square foot elevated home (there are 16 steps to enter and exit) featuring wide open floor plan with vault ...
From $215 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Luxury Beach Front Condo on the most private and select beach in Longboat Key.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Are you looking for a quiet and select, non-touristy location right on what happens to be one of the most spectacular an ...
From $240 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Newly Remodeled! Directly Across from Beach ~ Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. T ...
From $198 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Beautiful views from your lanai! Call for your getaway.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
• Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, st ...
From $191 per night (USD)
VRBO
From $176 per night (USD)
VRBO
Canal front cottage, walking distance to sandy Gulf
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comforts of home with a fully equipped kitchen and washer/dryer. New queen and XL twin beds. Bedding and sheets supplie ...
From $176 per night (USD)
VRBO
$Cedars East Unit #521 2BR\/2.5BA Condo Longboat Key- updated- 1440 sqft$
From $225 per night (USD)
VRBO
Cedars East Unit #521 2BR\/2.5BA Condo Longboat Key- updated- 1440 sqft
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Cedars Tennis Resort, is a luxury vacation rental on Longboat Key, close to Sarasota and world renowned St Armand's Circ ...
From $225 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Newly Renovated Tree House Condo Across The Street to the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the outdoor heated pool or take a 1 min stroll across the street to the Gulf of Mexico where our pristine beaches ...
From $360 per night (USD)
VRBO
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VRBO
Gulf Beach Resort - B
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Unit Features: 1-bedroom, 1-bathroom unit in the Orange Building Layout Note: Please note, the front door to unit 245 op ...
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VRBO
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Expedia
Gulf Beach Resort - A
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
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Expedia
From $294 per night (USD)
VRBO
Unit #212 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tastefully renovated, non-smoking, second floor unit. New updates every year. Light and bright with all the comforts of ...
From $294 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Unit #211 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2 bedroom 2 bath condo on the 2nd floor featuring over 1200 sq. with a beach theme. This unit was recently re ...
From $326 per night (USD)
Expedia
From $604 per night (USD)
VRBO
Bird's eye beach view by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this island getaway is located on the southern tip of Longboat Key with beautiful bea ...
From $604 per night (USD)
VRBO
$Hidden Bay\/Beach Paradise$
From $655 per night (USD)
VRBO
Hidden Bay\/Beach Paradise
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away fro ...
From $655 per night (USD)
VRBO
From $734 per night (USD)
VRBO
Tasteful 2brm Beachfront luxury
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large Living, dini ...
From $734 per night (USD)
VRBO
From $800 per night (USD)
Expedia
FANTASTIC COTTAGE ON LONG BOAT KEY FLORIDA...WEEK OF March 30- April 6 2024
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
WE ARE RENTING A FANTASTIC KEYWEST STYLE COTTAGE ON THE BEACH OF LONGBOAT KEY FLORIDA JUST STEPS TO THE SANDY BEACH OF T ...
From $800 per night (USD)
Expedia
$2\/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)$
From $335 per night (USD)
VRBO
2\/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sand Cay resort is open using the industries best practices and guidelines to ensure that all CDC sanitizing guidelines ...
From $335 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Unit #207 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Second floor,.. It's very cozy with all the comforts of home. This renovated unit has an updated kitchen and baths wit ...
From $326 per night (USD)
Expedia
From $630 per night (USD)
VRBO
Welcome to a Boaters dream!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept w ...
From $630 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Luxurious Beachfront Suite by FVC
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Offered by Florida Vacation Connection, enjoy this spacious 650 square feet beachfront Club Suite. This perfect island ...
From $337 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Direct Gulf front Condo on top floor, corner unit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Turtle Crawl Inn encompass all that is hallmark to a Gulf front vacation. Many others on the island claim to be Gulf ...
From $304 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Wonderful beach condo, heated pool, peaceful location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This large and airy 2 bedroom condo is right on the beach. It is a corner unit on the ground floor and it is very privat ...
From $360 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Sea Grape Inn #1- Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACH FRONT Condo- 1st Floor of Beach Front Property, 2 BDRM/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...
From $520 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Gulf Front 1 BR with Great Room Awesome View End Unit 227 with 42' TV
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Spend some time in paradise! Relax in a comfortable Laz Boy Recliner overlooking the Gulf. Enjoy breakfast while watchi ...
From $400 per night (USD)
VRBO
From $106 per night (USD)
VRBO
Float Above The Waves In Paradise - Beach Front, 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have two units in this condo building. One on the 2nd floor and one on the 7th. Both with magnificent Gulf of Mexic ...
From $106 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Modern Bayfront Retreat with boat dock and short walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This lovely 3 bedroom, 3 bath home waterfront hideaway will take you to another place and time. This treetop house is t ...
From $336 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Beachcomber unit 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beautifully renovated 1 bedroom, 1 bath ...
From $254 per night (USD)
VRBO
$*** OCEAN FRONT STUDIO SPECIAL *** FROM $99\/NIGHT$
From $197 per night (USD)
VRBO
*** OCEAN FRONT STUDIO SPECIAL *** FROM $99\/NIGHT
Bedrooms:
1
Bathrooms:
0
Sleeps:
3
*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT This complex is a two-story building with only 14 condos, beautiful ...
From $197 per night (USD)
VRBO
$Lido Beach House\n$
From $400 per night (USD)
VRBO
Lido Beach House\n
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Cozy beach house on stunning Lido Key 3 Bedrooms and 3 bathrooms with rooftop deck Beautiful private heated pool and spa ...
From $400 per night (USD)
VRBO
From $297 per night (USD)
VRBO
PENTHOUSE DOUBLE BALCONY FULL GULF & BAY VIEWS FROM EVERY ROOM Beachplace 5-602
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WELCOME TO Longboat Key, Florida! Our beautiful PENTHOUSE UNIT at BEACHPLACE, named “Bird’s Eye View”, has a breathtak ...
From $297 per night (USD)
VRBO
$Amazing 2\/2 Condo LBK w\/ Spectacular Bay Views!$
From $325 per night (USD)
VRBO
Amazing 2\/2 Condo LBK w\/ Spectacular Bay Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located on the famous Longboat Key, it offers a unique experience with a 180 degree Sarasota Bay view. Located on Dream ...
From $325 per night (USD)
VRBO
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VRBO
Longboat Key Oasis, golf course water views, pool, hottub
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Luxury living behind the gates of Longboat Key Club. Your private villa overlooks the Signature 5th hole of Longboat Key ...
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VRBO
$*** OCEAN FRONT STUDIO SPECIAL *** FROM $99\/NIGHT$
From $199 per night (USD)
VRBO
*** OCEAN FRONT STUDIO SPECIAL *** FROM $99\/NIGHT
Bedrooms:
1
Bathrooms:
0
Sleeps:
3
*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT . This complex is a two-story building with only 14 condos, beautiful ...
From $199 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Spacious and Bright Townhome on beautiful Longboat Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to Longboat Key - paradise awaits! Large newly renovated, spacious and bright 2 bed/2.5 bath 3 story townhome w ...
From $223 per night (USD)
VRBO
From $1424 per night (USD)
VRBO
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience f ...
From $1424 per night (USD)
VRBO
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VRBO
Not Currently Available
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Four Winds Beach Resort is located on Longboat Key Island, just off the shores of Sarasota, Florida. Come enjoy the san ...
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VRBO
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Expedia
Just 130 steps from your walk-out balcony to the Beautiful White Sand Beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tasteful and very clean 1500sq ft. 1st Floor 2 bedroom/2bath condo with all the amenities of home! Enjoy the ability to ...
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Expedia
From $349 per night (USD)
VRBO
AMAZING OCEAN VIEWS FROM PRIVATE BALCONY
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Beach Resort is located on exclusive Long Boat key a 12-mile long barrier Island off the Florida peninsula coast. He ...
From $349 per night (USD)
VRBO
From $2000 per night (USD)
VRBO
Steps to Beach-Beautiful gulf views and infinity pool. Exquisite!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Endless gulf views in newly constructed spectacular home with private infinity pool. This unit features a brand new mod ...
From $2000 per night (USD)
VRBO
From $129 per night (USD)
Expedia
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
GULF FRONT! One minute walk to the beach. No street crossing. Please be Advised before booking that this condo doesn't ...
From $129 per night (USD)
Expedia
From $185 per night (USD)
VRBO
A vacation condo like a home
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Our condo is located on the north end of Longboat Key, about 2 1/2 miles from Coquina Beach. We are between the Gulf of ...
From $185 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Tropical Paradise - boutique house and cottage with outdoor entertainment deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This house, located in a prime location next door to the best restaurant on the Island, is a tropical paradise that you ...
From $350 per night (USD)
Expedia
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VRBO
Penthouse timeshare
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
A rare opportunity to escape to your four bedroom penthouse on the beach in Longboat Key or for a week in February (2/5/ ...
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VRBO
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Expedia
Veranda Beach Club, beachfront Longboat Key, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit #309, a beach front condo, is available Weeks #51 & #52 2019, and Week #1 2020. Unit #306, with a partial ocean vi ...
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Expedia
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VRBO
Longboat Key’s rare location!Beautiful canal front house with a private dock!
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This wonderful, remodeled, neat unit has one bedroom king size bed with walk in closet and private bathroom, living room ...
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VRBO
From $239 per night (USD)
VRBO
Wonderful Canal Front Condo! Bring Your Boat!UNIT 11
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This beautiful and comfortable unit 11 has 1 bedroom and living room with sleeper sofa so it can easily accommodate 4 ...
From $239 per night (USD)
VRBO
From $489 per night (USD)
VRBO
Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Beach & Boaters Paradise a home in a residential community where you will have immediate access to beautiful ...
From $489 per night (USD)
VRBO
$Rare 3 Bedroom Condo\/Villa with Beautiful Bay Views$
From $276 per night (USD)
VRBO
Rare 3 Bedroom Condo\/Villa with Beautiful Bay Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy beautiful Bay views from this spacious three bedroom two bathroom one-story (no elevator) villa that comfortably s ...
From $276 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Beautiful Beachplace - 1135 Gulf of Mexico Drive
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy spectacular sunsets from this direct Gulf front, 2 bedroom, 2 bath well appointed property. Located on the 5th flo ...
From $144 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Beachfront Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Steps to the heated pool and gorgeous beach - which runs for over ten miles! Run out barefoot to the beach, enjoy a swim ...
From $310 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Condo with Beach access and just minutes from St. Armand Circle
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The perfect beach getaway! Gulf front community with excellent amenities includes a private beach with beach chairs for ...
From $250 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Longboat Village Getaway: House on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into tranquility with Longboat Village Getaway, a charming two-bedroom, two-bathroom stilted home nestled on the pe ...
From $159 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Beautiful Portobello Condo with Tennis, Heated Pool and Private Beach unit B305
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
MONTHLY/SEASONAL RENTAL! Welcome to Paradise. This very comfortable and spacious 3rd floor, 1500 sqft 2 bed/2 bath condo ...
From $144 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Directly on the sand of private beach on Longboat key, closest to the ocean.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Updated for 2024! Ground floor Condo with two steps that lead out the back lanai to the white sands of the private beach ...
From $428 per night (USD)
VRBO
From $352 per night (USD)
VRBO
2 BR Beach front villa with enclosed north bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom home with a split floor plan works beautifully to accommodate your family's vacation. You walk into a wel ...
From $352 per night (USD)
VRBO
From $214 per night (USD)
VRBO
North End Villa Spacious Longboat Key Villa minutes walk to a private beach grill, WIFI, PERFECT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You can’t get closer to a private beach without the beach front price tag! Longboat has monthly rentals but will rent fo ...
From $214 per night (USD)
VRBO
$Beachplace 4-604 Luxurious 2 BR\/2 BA Penthouse Condo.$
From $200 per night (USD)
VRBO
Beachplace 4-604 Luxurious 2 BR\/2 BA Penthouse Condo.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stunning, Fully Furnished, Penthouse, 2 BR/2BA Condo With Amazing Views! Recently remodeled to give a cozy yet sophist ...
From $200 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Club Suite at Longboat Key Club
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Peaceful water views from this lovely lagoon junior suite at The Inn on the Beach, behind the gates of the Resort at Lon ...
From $500 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Retreat Between the Beach & Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The quaintness of our condo and its location are unmatched. This 2B/2B unit is steps away from the bay, and merely acros ...
From $250 per night (USD)
VRBO
From $890 per night (USD)
VRBO
St. Armand's Canal-Front Pool Home
Bedrooms:
8
Bathrooms:
4
Sleeps:
8
St. Armand's Canal-Front Pool Home steps to the beach! This gem of an estate has been completely rebuilt and remodeled. ...
From $890 per night (USD)
VRBO
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VRBO
Beach Therapy! Sophisticated St. Armand's Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Sophisticated and modern updated St. Armand's pool home attends to every detail to achieve a wonderfully relaxing vacati ...
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VRBO
From $230 per night (USD)
VRBO
Your Paradise Awaits...
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Enjoy the ambiance of this Key West style bungalow, one of the earliest properties in the charming Long Beach Village. R ...
From $230 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Home On Canal, Bring Boat & Kayaks, Minutes to Beaches, Dog* (See Note)...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
**ASK ABOUT LAST MINUTE DEALS! Willow Bay is a perfect location for any large family gathering. Located in ...
From $240 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Beachplace Beachfront-Special rate for May
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wake up to sparkling sea views, take a beach walk, raise a glass to a brilliant west coast sunset, listen to the waves, ...
From $230 per night (USD)
VRBO

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