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 $479 per night (USD)
VRBO
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 $479 per night (USD)
VRBO
From $364 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 $364 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Sparkling Clean, Updated 2BR/1BA Beach Condo. Unbeatable Location.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sparkling Clean, tastefully Updated 2BR/1BA Beach Condo — Unbeatable Walkable Location – Everything You Need is Steps Aw ...
From $226 per night (USD)
VRBO
From $1239 per night (USD)
Expedia
4 BR/3 BA Lido Canal Home by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Offered by FL Vacation Connection, you will find that everything you want for your perfect vacation is right here, and i ...
From $1239 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
From $360 per night (USD)
VRBO
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 $360 per night (USD)
VRBO
From $284 per night (USD)
VRBO
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 $284 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Amazing Beachfront 2B/2B in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
October and November 2021 are still available with Deep Discount Prices! Wonderful Beachfront condo in magnificent Lo ...
From $136 per night (USD)
VRBO
From $257 per night (USD)
VRBO
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 $257 per night (USD)
VRBO
$Gulf-Front - Anna Maria Island\nApril 2026 Discount Available$
From $339 per night (USD)
VRBO
Gulf-Front - Anna Maria Island\nApril 2026 Discount Available
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Full Gulf-Front Condominium in well maintained complex. Secured building and covered parking (1 space). Beautiful pool, ...
From $339 per night (USD)
VRBO
From $685 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 $685 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Exclusive Beach-Style Condo with great Gulf-View 🌅 Sand Cay 206, Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
🌴Exclusive Gulf View Condo – Sand Cay Beach Resort, Unit 206, Longboat Key 🌴 Welcome to Longboat Key, one of the most ...
From $381 per night (USD)
VRBO
From $1449 per night (USD)
VRBO
AMI Group Stay! Pool, Spa & Rooftop Deck
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
Crystal Waves Oasis by AMI Locals 108 11th St S, Bradenton Beach, Florida TPL21-000121 Welcome to Crystal Waves Oasi ...
From $1449 per night (USD)
VRBO
From $390 per night (USD)
Expedia
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 $390 per night (USD)
Expedia
From $493 per night (USD)
VRBO
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 $493 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $367 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 $367 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Tennis Tranquility at Cedars East Unit #519–Steps to Courts and Pool by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $293 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Peaceful Longboat Key Canal Home
Bedrooms:
1
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 $193 per night (USD)
VRBO
From $208 per night (USD)
Expedia
End-Unit Beach Villa w Stunning Views–Spacious 2BR Whitney Beach #336 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 $219 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 $219 per night (USD)
VRBO
From $396 per night (USD)
Expedia
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 $396 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 ...
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VRBO
From $326 per night (USD)
Expedia
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 $326 per night (USD)
Expedia
From $355 per night (USD)
VRBO
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)
VRBO
From $278 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 $278 per night (USD)
VRBO
From $185 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 $185 per night (USD)
VRBO
From $420 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 $420 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 $407 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 $407 per night (USD)
VRBO
From $822 per night (USD)
Expedia
Hidden Bay/Beach Paradise
Bedrooms:
3
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 $822 per night (USD)
Expedia
From $978 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 $978 per night (USD)
VRBO
From $420 per night (USD)
VRBO
2/2 GULF SIDE UPDATED APT.. SPECIAL 9/1 TO 11/1-LOW SUMMER RATES, 195 PER NIGHT
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 $420 per night (USD)
VRBO
From $418 per night (USD)
VRBO
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 $418 per night (USD)
VRBO
From $475 per night (USD)
Expedia
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 $475 per night (USD)
Expedia
From $487 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 $487 per night (USD)
VRBO
From $506 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 $506 per night (USD)
VRBO
From $478 per night (USD)
VRBO
Float Above The Waves In Paradise - Beach Front, 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
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 $478 per night (USD)
VRBO
From $476 per night (USD)
Expedia
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 $476 per night (USD)
Expedia
From $280 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 $280 per night (USD)
VRBO
From $551 per night (USD)
VRBO
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 $551 per night (USD)
VRBO
From $457 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 $457 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Cedars East Townhome on beautiful Longboat Key
Bedrooms:
2
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 $277 per night (USD)
Expedia
From $1564 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 $1564 per night (USD)
VRBO
From $321 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 $321 per night (USD)
Expedia
From $2068 per night (USD)
VRBO
Steps to Beach-Full gulf views infinity pool-EXQUISITE! Ask @ summer specials!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Endless gulf views in newly constructed spectacular home with private infinity pool. This unit features a brand new mod ...
From $2068 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
From $500 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 $500 per night (USD)
VRBO
From $258 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 $258 per night (USD)
VRBO
From $481 per night (USD)
VRBO
Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Beach & Boaters Paradise a home in a residential community where you will have immediate access to beautiful ...
From $481 per night (USD)
VRBO
From $314 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 $314 per night (USD)
VRBO
From $241 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 $241 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Charming Longboat Village Hideaway–2BR in a Quiet Coastal Neighborhood 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 $459 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Beautiful Portobello Condo Steps to Private Beach, Tennis and Pool
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 $278 per night (USD)
VRBO
From $528 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 $528 per night (USD)
VRBO
From $240 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 $240 per night (USD)
VRBO
From $290 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 $290 per night (USD)
VRBO
From $1404 per night (USD)
VRBO
Precise Realty presents The Canal Breeze Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
St. Armand's Canal-Front Pool Home steps to the beach! This gem, ranch style home estate has been completely rebuilt ...
From $1404 per night (USD)
VRBO
From $337 per night (USD)
VRBO
Your Paradise Awaits...
Bedrooms:
3
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 $337 per night (USD)
VRBO
From $537 per night (USD)
VRBO
Longboat Bay Club, Longboat Key Florida, Condo
Bedrooms:
2
Bathrooms:
2
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 $247 per night (USD)
VRBO
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 $247 per night (USD)
VRBO
From $1050 per night (USD)
Expedia
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 NO CANCELATION FEES Cancellation Policy (Effective for reservations ...
From $1050 per night (USD)
Expedia
From $256 per night (USD)
VRBO
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 $256 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 $284 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 $284 per night (USD)
VRBO
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 $156 per night (USD)
VRBO
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 $156 per night (USD)
VRBO
From $237 per night (USD)
VRBO
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 $237 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Amazing Gulf Beach Condo Steps From The Sand
Bedrooms:
2
Bathrooms:
2
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)
VRBO
From $494 per night (USD)
Expedia
Sea Grape Inn #6- 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 $494 per night (USD)
Expedia
$Gulf Front Luxury - \Serenity Sunset\ - Long Boat Key, FL$
From $217 per night (USD)
VRBO
Gulf Front Luxury - \"Serenity Sunset\" - Long Boat Key, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upsc ...
From $217 per night (USD)
VRBO
From $208 per night (USD)
Expedia
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Gray House is a completely renovated historical cottage dating back to the early 1900s, in the historical fishing vi ...
From $208 per night (USD)
Expedia
From $274 per night (USD)
VRBO
New Listing: Sun, Sea Breeze & Seagulls – The Ultimate Beach Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the heart of Longboat Key Gulf Key provides it’ guest with one of the best locations on the key. With two (2) ...
From $274 per night (USD)
VRBO
From $676 per night (USD)
Expedia
Coquina Moorings 201 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath with...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coquina Moorings, Unit 201 - Anna Maria Island - 2 Bedroom/ 2 Bath with Den, maximum occupancy of 6 people. Bay an ...
From $676 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Recently Updated!!! Lovely 2 Bedroom Condo in Bayport Beach and Tennis Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This tastefully furnished, second-floor condo in the Bayport Beach and Tennis Club offers a comfortable living space wit ...
From $215 per night (USD)
VRBO
From $481 per night (USD)
VRBO
Precise Realty presents Coastal Bliss on Longboat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Booked February 1st through April 30th 2026. 3 month rental required. Located directly on the beach, this remodeled 2/2 ...
From $481 per night (USD)
VRBO
From $800 per night (USD)
VRBO
637 Norton - Longboat Key - Private canal home 4 Bedroom/ 3.5 Bath with...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
637 Norton - Longboat Key - 4 Bedroom/ 3.5 Bath, maximum occupancy of 8 people. Canal Home - Private Pool - Boat D ...
From $800 per night (USD)
VRBO
From $396 per night (USD)
VRBO
Longboat Harbour towers
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This beautiful condo is furnished in island style furniture. It includes an inside entry, washer/dryer, big screen TV, f ...
From $396 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Walk to Everything, Gulf Views, Waterfront, Heated Resort Style Pool w/ Slide
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...
From $1759 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Beach, Boat & Paws–Pet-Friendly Pool Home Blue Heron in Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blue Heron House by RVA. This three-bedroom plus office, two-bathroom house is located on the Northern end of ...
From $532 per night (USD)
Expedia
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VRBO
Ocean view Longboat Key condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 BR/2 BA spacious condo timeshare at the Veranda Beach Club in Longboat Key with Gulf of Mexico views from the balcony. ...
Click For Pricing
VRBO
From $301 per night (USD)
Expedia
Direct bayfront views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views ...
From $301 per night (USD)
Expedia
From $276 per night (USD)
VRBO
LONGBOAT KEY BEAUTY! This 2/2 unit offers stunning views of the bay! Call today to book your fall vacation!
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 $276 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Right on the beach.Renovated ground Floor unit 63.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Completely renovated. Everything is new. Amazing location. Charming studio right on the beach. Condo management will h ...
From $334 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Bright Key West style home on the Longboat Key-Walk to the Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a great vacation home on the north end of Longboat Key near Longboat Pass. This home is set on a lovely bayou and ...
From $500 per night (USD)
VRBO
Click For Pricing
Expedia
beachfront condo on 6th floor of the longboat key club resort !
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
6th floor bedroom king suite with 1 bathroom living room area with pull out queen bed and kitchen with washer dryer con ...
Click For Pricing
Expedia
From $229 per night (USD)
VRBO
Upscale Beachplace Condo...availability starting in May 2026....please inquire
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LATEST NEWSFLASH FOR BEACHPLACE UNIT 4-404: * 2025 and Winter season 2026 have been fully booked. First available date ...
From $229 per night (USD)
VRBO
From $452 per night (USD)
VRBO
LONGBOAT KEY BEACH CONDO
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Longboat Key (LBK) Family Home. Our condo is a true family home where we gather together to get away fr ...
From $452 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Beachplace - 6 305, 3 Bedroom Condo with Gulf and Bay views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
All the bells and whistles! This is a gorgeous 3 bedroom/2 bath corner unit with wrap around windows! Beautiful open con ...
From $276 per night (USD)
VRBO
From $179 per night (USD)
Expedia
2 Bd/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Available from June 1st - December 15, 2023. Long-term renter desired. Beautiful corner unit condo with an abundance of ...
From $179 per night (USD)
Expedia
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VRBO
Gulf Front 3 bedroom Condo in Club Longboat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful, ground floor, gulf front, condo in Club Longboat features two full bedrooms, two full baths, a den with ...
Click For Pricing
VRBO
From $381 per night (USD)
Expedia
Updated Townhome, Secluded Beach + Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Renovation completed in 2025! New master bath, whole house repaint, new furniture, etc. Longboat Key beach is ok post-hu ...
From $381 per night (USD)
Expedia
From $318 per night (USD)
VRBO
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Perfect, private retreat! Time slips into Beach time, where nature guides your days and evenings. Fully renovated post 2 ...
From $318 per night (USD)
VRBO
From $372 per night (USD)
VRBO
We Are Open! No damage to our Beautiful Beachfront Condo on Gulf of Mexico
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hi everybody, we are happy to report that our unit incurred no damage and our association had only minimal damage due to ...
From $372 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Lido Key Getaway With Heated Private Pool and Private Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This amazing mid-century modern home is the perfect Lido Key getaway for relaxation and vacation in Florida. Steps from ...
From $371 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Longbeach Lucky 13: Where Island Time Begins & Relaxation Never Ends by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
No luck needed here to know you've stumbled upon one of the best spots Longboat Key has to offer. Longbeach Lucky 13 by ...
From $368 per night (USD)
Expedia
Click For Pricing
VRBO
Spectacular Views of Beach and Bay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
3 month minimum rental no smoking no pets. We are renting our turnkey condo fully furnished including all utilities. The ...
Click For Pricing
VRBO
From $312 per night (USD)
Expedia
Exquisite Beachfront Condo with both Sunrise & Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A tropical treasure is waiting for you. Newly renovated beachfront beauty with Tommy Bahama inspired furnishings through ...
From $312 per night (USD)
Expedia

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