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 $555 per night (USD)
VRBO
Sea Grape Inn #7 - Beachfront Property
Bedrooms:
2
Bathrooms:
3
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 $555 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Sea Grape Inn #5- Beachfront Property
Bedrooms:
2
Bathrooms:
3
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 $955 per night (USD)
Expedia
From $955 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 $955 per night (USD)
VRBO
From $364 per night (USD)
Expedia
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 $364 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Spectacular 5-star Condo. Walk to beach & restaurants. Just remodeled.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you're seeking a romantic getaway, a family vacation, or simply a peaceful escape, look no more! This newly remo ...
From $266 per night (USD)
VRBO
$4 BR\/3 BA Lido Canal Home by FVC$
From $1172 per night (USD)
Expedia
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 $1172 per night (USD)
Expedia
From $229 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 $229 per night (USD)
VRBO
$On the beach, Sunset view, Monthly rental 2B\/B2 Pool&Tennis$
From $304 per night (USD)
Expedia
On the beach, Sunset view, Monthly rental 2B\/B2 Pool&Tennis
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 $304 per night (USD)
Expedia
From $227 per night (USD)
VRBO
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 $227 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Beachcomber unit 401
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $326 per night (USD)
VRBO
$Amazing Beachfront 2B\/2B in Longboat Key$
From $161 per night (USD)
Expedia
Amazing Beachfront 2B\/2B in Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
October and November 2021 are still available with Deep Discount Prices! Wonderful Beachfront condo in magnificent Lo ...
From $161 per night (USD)
Expedia
From $206 per night (USD)
VRBO
1st Floor Home Away from Home - Steps to Beach - Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A very warm welcome to your beautiful, home away from home on this Island Paradise! This gorgeous location is truly on ...
From $206 per night (USD)
VRBO
From $396 per night (USD)
Expedia
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 $396 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Gulf Getaway with Porch + Direct Beach Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in th ...
From $320 per night (USD)
VRBO
From $1478 per night (USD)
Expedia
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 $1478 per night (USD)
Expedia
From $429 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 $429 per night (USD)
VRBO
From $1819 per night (USD)
Expedia
Paradise awaits at this sparkling 7 bedroom luxury home with pool & rooftop deck
Bedrooms:
7
Bathrooms:
8
Sleeps:
18
Crystal Waves Oasis by Anna Maria Island Locals Home in Bradenton Beach, FL Features: • Private Pool and Spa • Rooftop ...
From $1819 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Your Coastal Oasis at Cabana Beach Club Unit 8! NO MAJOR HURRICANE DAMAGE!!! Just a two-minute stroll from pr ...
From $349 per night (USD)
VRBO
$GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH$
From $470 per night (USD)
Expedia
GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key! Magnific ...
From $470 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Welcome to your Beach Front Dream Condo! LBKTP102
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf Front Longboat Key Vacation Rental! 2 bedrooms, 2 baths, over 1300 square feet under air, walk right out to the bea ...
From $303 per night (USD)
VRBO
From $367 per night (USD)
Expedia
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 $367 per night (USD)
Expedia
From $366 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 $366 per night (USD)
VRBO
From $352 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 $352 per night (USD)
Expedia
From $315 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 $315 per night (USD)
VRBO
From $208 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 $208 per night (USD)
Expedia
From $274 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 $274 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Longboat Key Club!! Direct Beachfront!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming poo ...
From $424 per night (USD)
Expedia
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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 ...
Click For Pricing
VRBO
From $1485 per night (USD)
Expedia
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 $1485 per night (USD)
Expedia
$This AMAZING 2\/2 has stunning views of the bay!$
From $267 per night (USD)
VRBO
This AMAZING 2\/2 has stunning views of the bay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...
From $267 per night (USD)
VRBO
From $355 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 $355 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
From $132 per night (USD)
Expedia
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 $132 per night (USD)
Expedia
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VRBO
Outrigger Resort by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
<p>While you're here, you can enjoy all the comforts of home and more, including a refrigerator and free WiFi, as well a ...
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VRBO
$Cedars East 2BR\/2.5BA Condo Longboat Key- recently updated- 1440 sqft$
From $574 per night (USD)
Expedia
Cedars East 2BR\/2.5BA Condo Longboat Key- recently 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 $574 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Newly Renovated Tree House Condo Across The Street to the Beach!
Bedrooms:
2
Bathrooms:
3
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 $420 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
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 ...
Click For Pricing
VRBO
From $428 per night (USD)
Expedia
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 $428 per night (USD)
Expedia
Click For Pricing
VRBO
Inn on the Beach 3007 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 ...
Click For Pricing
VRBO
$Hidden Bay\/Beach Paradise$
From $805 per night (USD)
Expedia
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 $805 per night (USD)
Expedia
From $929 per night (USD)
VRBO
Luxury 2 bedroom Beachfront Condo by FVC
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 $929 per night (USD)
VRBO
$FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3\/29 - 4\/5 2025$
From $678 per night (USD)
Expedia
FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3\/29 - 4\/5 2025
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
WE ARE RENTING A FANTASTIC KEY WEST STYLE COTTAGE ON THE BEACH OF LONGBOAT KEY FLORIDA. JUST STEPS TO THE LOVELY BEACH ...
From $678 per night (USD)
Expedia
$2\/2 GULF SIDE UPDATED APARTMENT$
From $432 per night (USD)
VRBO
2\/2 GULF SIDE UPDATED APARTMENT
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 $432 per night (USD)
VRBO
From $427 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 $427 per night (USD)
Expedia
From $1064 per night (USD)
VRBO
Luxurious Beachfront Suite by FVC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Proudly offered by Florida Vacation Connection, this beautifully updated 650-square-foot beachfront Suite (also known as ...
From $1064 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Direct Gulf front Condo on top floor, corner unit
Bedrooms:
1
Bathrooms:
2
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 $389 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Wonderful beach condo, heated pool, peaceful location Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
On the beach! Wonderful 2 BR condo This large and airy 2 bedroom condo is right on the beach. It is a corner unit on th ...
From $406 per night (USD)
VRBO
From $673 per night (USD)
Expedia
Sea Grape Inn #1- Beachfront Property
Bedrooms:
2
Bathrooms:
3
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 $673 per night (USD)
Expedia
From $481 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 $481 per night (USD)
VRBO
From $123 per night (USD)
Expedia
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 $123 per night (USD)
Expedia
From $209 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 $209 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Beachcomber unit 205
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our building is located on the beach, this unit has an ISLAND view. Beautifully renovated 1 bedroom, 1 bath ...
From $321 per night (USD)
Expedia
$Lido Beach House\n$
From $499 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 $499 per night (USD)
VRBO
From $355 per night (USD)
Expedia
PENTHOUSE DOUBLE BALCONY FULL GULF & BAY VIEWS FROM EVERY ROOM Beachplace 5-602
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our beautiful PENTHOUSE UNIT at BEACHPLACE, named “Bird’s Eye View”, has a breathtaking view of the Gulf of Mexico from ...
From $355 per night (USD)
Expedia
$Stunning 2\/2 Condo LBK with Bay Views & Boat Slip Rental!$
From $444 per night (USD)
VRBO
Stunning 2\/2 Condo LBK with Bay Views & Boat Slip Rental!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Longboat Key is perfect for a dream vacation on an island! This condo offers a stunning 180-degree view of Sarasota Bay. ...
From $444 per night (USD)
VRBO
From $234 per night (USD)
Expedia
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 $234 per night (USD)
Expedia
From $1638 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 $1638 per night (USD)
VRBO
$Now Open! 7-Night Deal – Oceanfront w\/ Private Balcony & Stunning Views$
From $413 per night (USD)
Expedia
Now Open! 7-Night Deal – Oceanfront w\/ Private Balcony & Stunning Views
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 $413 per night (USD)
Expedia
From $1566 per night (USD)
VRBO
Steps to Beach-Full gulf views infinity pool. EXQUISITE! No hurricane damage
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 $1566 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Renovated Beach Paradise. Ground Floor unit 64
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Completely renovated. Everything is new. Amazing location. Condo management will help you with your accommodation. The u ...
From $311 per night (USD)
Expedia
From $211 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 $211 per night (USD)
VRBO
From $589 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 $589 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
From $285 per night (USD)
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 ...
From $285 per night (USD)
VRBO
From $283 per night (USD)
Expedia
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 $283 per night (USD)
Expedia
From $429 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 $429 per night (USD)
VRBO
$Rare 3 Bedroom Condo\/Villa with Beautiful Bay Views$
From $314 per night (USD)
Expedia
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 $314 per night (USD)
Expedia
From $353 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 $353 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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 $241 per night (USD)
Expedia
From $455 per night (USD)
VRBO
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 $455 per night (USD)
VRBO
From $236 per night (USD)
Expedia
JANUARY 1-30 2026 AVAIL. Beautiful Portobello Tennis Pool & Private Beach
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 $236 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Beachfront 1-bedroom condo in Longboat Key, Private beach in your backyard.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the ultimate beach lifestyle with this ground-floor condo at Silver Sands Resort, where your back lanai steps ...
From $500 per night (USD)
VRBO
From $474 per night (USD)
Expedia
2 BR Beach front villa with enclosed lanai overlooking the pool
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 $474 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
$Beachplace 4-604 Luxurious 2 BR\/2 BA Penthouse Condo.$
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Retreat Between the Beach & Bay
Bedrooms:
2
Bathrooms:
4
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 $290 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
St. Armand's Canal-Front Pool Home
Bedrooms:
4
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 $1148 per night (USD)
Expedia
From $436 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 $436 per night (USD)
VRBO
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Expedia
Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully furnished beach front property, Second floor corner garden unit with two balconies. Private beach with umbr ...
Click For Pricing
Expedia
From $537 per night (USD)
VRBO
Longboat Bay Club, Longboat Key Florida, Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently renovated over the last 2 years 1600 sq. ft. 2 bedroom, 2 baths, sleeps 6, pool, hot tub, tennis court, outdoor ...
From $537 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Longboat Key , Beach , Pool , Dock , Canal , Boat Access. Kayak rentals, Fishing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Large open rooms, Canal for Kayaking and Boating - 2800 sq ft, 4 Bedroom, 3 Bath, Beach, Pool Large Longboat Key Home - ...
From $238 per night (USD)
Expedia
From $1363 per night (USD)
VRBO
Mermaid's Landing managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
110 11th Street South - Bradenton Beach - FL 34217 Book with confidence: You may cancel your reservation up to 60 days ...
From $1363 per night (USD)
VRBO
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Expedia
BEAUTIFUL GULF-VIEW CONDO
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Spectacular balcony and window views sitting on the Gulf. Private beach, swimming pool and tennis court. Spacious unit ...
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Expedia
From $276 per night (USD)
VRBO
Discounted rates for May! This beautiful unit has front row seats to the sunrise! Direct bayfront!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Harbour Villa #305 was just recently updated with a brand new fully stocked kitchen from appliances to counter tops and ...
From $276 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Longboat Key with Gulf to Bay access. Beautiful view of Bishop's Bayou.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Outdoor living at its best in this updated WATERFRONT first floor condo in Whitney Beach Bay Side. Mesmerizing views of ...
From $230 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Breathtaking Beach Front Property Ground Floor Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Granite and stainless steel appliances in the kitchen. The living room’s sliding patio door provides first floor access ...
From $327 per night (USD)
VRBO
Click For Pricing
Expedia
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
This spacious 4.5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a lar ...
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Expedia
From $325 per night (USD)
VRBO
Undamaged - Can't Get Closer to the Beach Without Getting Your Feet Wet!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We were extremely lucky. Storm surge from Helene stopped 10 feet from our Lanai. We were on "safe" side of Milton that l ...
From $325 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Spectacular Sarasota Bay Views from all rooms
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seasonal Rental. Spectacular views of Sarasota Bay and the Gulf of Mexico from this island penthouse condo. Enjoy the ma ...
From $289 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Beautiful Condo Overlooking Gulf - Multiple Monthly Rental Preferred
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Manatee County Condo RRCR# RRR-00751.2023 Wake up to the amazing sounds and beautiful views of the Gulf of Mexico! We ...
From $315 per night (USD)
VRBO
$Gulf-Front - 2 1\/2 bedroom, 2 Baths$
From $232 per night (USD)
Expedia
Gulf-Front - 2 1\/2 bedroom, 2 Baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
On LBK’s laid-back, beachy North End: A 26-foot lanai overlooks a pristine stretch of dune and the wide, under-populate ...
From $232 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Best desired location on Southern end of LBK in Country Club Shores
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Private home located in the prime desirable quiet neighborhood of Country Club Shores. (sought after southern end with ...
From $452 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Amazing Gulf Beach Condo Steps From The Sand
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a small cozy 5 STAR rated Time Share Rental Property with less then 50 units in the middle of the 11 mile beach ...
From $380 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Sea Grape Inn #6- Beachfront Property
Bedrooms:
2
Bathrooms:
3
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 $547 per night (USD)
VRBO
From $555 per night (USD)
Expedia
Sea Grape Inn #2- Beachfront Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper, ...
From $555 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Oceanview Beautiful Penthouse 3 Rms Private Patios Spacious Steps to the Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
* DISCOUNTED RATE AVAILABLE FOR MORE THAN 90 DAYS. CONTACT OWNER FOR DETAILS* Life is good at Beach Harbor Club in Longb ...
From $340 per night (USD)
VRBO
$First level - steps to beautiful beach, Longboat Key\n$
From $297 per night (USD)
VRBO
First level - steps to beautiful beach, Longboat Key\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
First level - steps to beautiful beach, Longboat Key This condo is located on gorgeous Whitney Beach, at the north end ...
From $297 per night (USD)
VRBO

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