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 $721 per night (USD)
VRBO
LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $721 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Unit #308 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bright and sunny; 3rd floor condo: Partial view to beach from private patio. Condo has Cathedral ceilings for spacious ...
From $400 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Unit #210 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Second floor, poolside. Directly over pool. This unit has had numerous upgrades this year including a complete kitchen ...
From $396 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Spacious 2BR Retreat | Walk to Beach + Bay Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our spacious condo, located directly facing the beautiful Crane's Bay. Our units, all measuring over 1600 sq. ...
From $270 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Gulf of Mexico Front Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 BR, 2 Bath, 1684 Sq. Ft., gulf front condo located within the Bayport Beach and Tennis Club on Longboat Key, Florida. ...
From $348 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Sand Between Your Toes, Smiles All Around
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Where flip-flops are the dress code, and your biggest dilemma is beach or pool first? This cheerful 1-bedroom, 2-bath c ...
From $237 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Seas the Day: Gulf-Front Bliss Awaits You!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up to the rhythmic waves of the Gulf and sip your morning coffee on your private beachfront balcony, where salty br ...
From $467 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Gulfside Escape at Sea Twig #103- Relax & Unwind Steps to Sand & Pool by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charmi ...
From $510 per night (USD)
Expedia
From $342 per night (USD)
VRBO
waterfront bungalow north end LBK-2 minute walk to beach (weekly availability)
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nicely updated 1 bedroom/1 bath on Greer Bay, North LBK. The largest beach on the island is just a short walk and the ba ...
From $342 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Long Boat Key Vacation Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
This is a two bedroom, two bathroom open layout condo with an ally kitchen and views of both the gulf and the bay. The c ...
From $209 per night (USD)
Expedia
From $725 per night (USD)
VRBO
Amazing Canal Front 4 Bedrm Home, Heated Pool, Dock Putting Green Close to Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Beautifully updated large home on a deep water canal with room for a boat. Resort-like setting with a heated pool, putti ...
From $725 per night (USD)
VRBO
$3 BEDROOM PENTHOUSE \CRUISE SHIP\ VIEWS w/DOUBLE BALCONY at Beachplace!$
From $685 per night (USD)
VRBO
3 BEDROOM PENTHOUSE \"CRUISE SHIP\" VIEWS w/DOUBLE BALCONY at Beachplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Full Wall-to-Wall renovation and re-imagined 3 Bedroom floor plan 2022! 6TH FLOOR PENTHOUSE "CRUISE SHIP" VIEWS WITH DOU ...
From $685 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Direct beachfront private home by FVC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical Odyssey, a beachfront 4 bedroom home managed by Florida Vacation Connection provides a screened porch with enou ...
From $320 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Buttonwood Cove 104B by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You can't beat the view from this lovely and spacious 2 bedroom, 2 bath, first floor condo! Your private, enclosed lanai ...
From $211 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Play by Day, Unwind by Night - Cedars East #852 Pet-Friendly by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...
From $278 per night (USD)
VRBO
From $514 per night (USD)
Expedia
650 Norton - Longboat Key - Canal Home with private Pool - 3 Bedroom/ 2 Bath,...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
650 Norton - Longboat Key - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - Distance ...
From $514 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Bayfront home with dock, amazing views, outdoor areas, & kayak
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Beach to Bay View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $295 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Unit #101 Sand Cay, Gulf View, Steps to Beach, Recently Remodeled
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This privately located ground floor Gulf View unit was just remodeled with new paint and new luxury vinyl flooring. Well ...
From $437 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Waterfront Longboat Key Retreat With Dream Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Start your days waking up to waterfront views and end your days watching the sunset on the Gulf of Mexico from your priv ...
From $282 per night (USD)
VRBO
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Expedia
White Sands 1BR Condo Bayside
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Indulge in a beach vacation at our one-bedroom, one-bath, pool-view condo, providing all the essentials for a perfect ge ...
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Expedia
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VRBO
1BR Townhouse, Pool and Bay Views, Patio and Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into this inviting two-story townhouse, where coastal charm meets relaxation. The one-bedroom, one-and-a-half-bath ...
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VRBO
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Expedia
Longboat Key 2BR Bayside Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
With tranquil pool views and all the essentials for a dreamy beach vacation, this idyllic retreat is the place to relax ...
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Expedia
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VRBO
Private Pool! 4 Bedroom Home
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
This bay-view home features four bedrooms and three baths, providing all the essential amenities for a beach vacation. T ...
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VRBO
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Expedia
2 BR Woods View Bayside Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a serene ground-level retreat with our inviting two-bedroom, two-bath condo nestled in a wooded paradise. Perf ...
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Expedia
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VRBO
Longboat Key 2BR/1Ba Bayside
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This two-bedroom, one-bath bayside villa offers all the essentials needed for a vacation at the beach. The kitchen is we ...
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VRBO
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Expedia
2BR Two Story Townhouse Balcony and Patio. Pool and Partial Bay Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bring your family to an unforgettable getaway in our spacious two-bedroom, two-bath townhouse at White Sands, Longboat K ...
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Expedia
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VRBO
Gulf Side Pool View 2BR Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Embark on an ideal beach vacation with our two-bedroom, two-bath ground floor condo overlooking the pool, providing all ...
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VRBO
From $213 per night (USD)
Expedia
Salt Air, Sunlight, and Old Florida Flair
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into a simpler time with this cozy Cape Cod-style cottage, where beach vacations feel timeless and the pace is set ...
From $213 per night (USD)
Expedia
From $347 per night (USD)
VRBO
2BR Cottage Bayside Time for Relaxation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape the daily hustle and embrace tranquility at this charming cottage with breathtaking bay views. The spacious main ...
From $347 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Longboat Key Cottage Steps to Pool and Bay Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Little Gull Cottage, a charming retreat with a spacious main bedroom featuring a king bed for ultimate comfor ...
From $359 per night (USD)
Expedia
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VRBO
Throwback Charm Meets Beach Bliss 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step back in time to the golden days of beach vacations—think breezy porches, tiki huts, and palm-fringed paths that lea ...
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VRBO
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Expedia
2BR Cottage Bayside Close to the Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Little Gull Cottage, where Cape Cod charm meets Longboat Key's natural beauty. This cozy retreat features a s ...
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Expedia
From $285 per night (USD)
VRBO
Charming Bayside 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the charm of this cottage, featuring a generously sized main bedroom with a king bed, providing a comfortable ...
From $285 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step back in time and settle into a slice of Old Florida at Little Gull Cottage, a 2-bedroom, 2-bath coastal retreat tha ...
From $412 per night (USD)
Expedia
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VRBO
Gulf-Front Charm with Old Florida Soul-2BR Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Flashback to the golden days of beach vacations, where sunsets were your screen time and nature was your entertainment. ...
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VRBO
From $345 per night (USD)
Expedia
2BR Cottage Bayside of Property, Full Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Key is a haven for wildlife lovers, where you might spot tortoises, egrets, wild parrots, and even the island?s ...
From $345 per night (USD)
Expedia
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VRBO
2BR Cottage Gulf Side of Property, Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking to relive the beach vacations of your childhood—minus the car fights and soggy bread? Welcome to your grown-up v ...
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VRBO
From $615 per night (USD)
Expedia
BEACH ACCESS, BEAUTIFUL HOME, WALK TO PARK & AMENITIES
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighborhood. Take a leisurely 5 ...
From $615 per night (USD)
Expedia
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VRBO
Private Longboat Key House on Water
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Open floor plan main living area with the great room almost 28ft in height. This home literally has everything you nee ...
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VRBO
From $403 per night (USD)
Expedia
Your Home Away from Home: Little Gull 4BR Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Situated bayside with breathtaking views, this four-bedroom cottage is the ideal spot for your Florida beach getaway. Th ...
From $403 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Relax and Recharge in this 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming bayside cottage, featuring a spacious main bedroom with a king bed and a living room with a fire ...
From $244 per night (USD)
VRBO
From $4734 per night (USD)
Expedia
Boater’s Paradise–Pool & Dock, Walk to Beach Seas the Day: Home in LBK by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Seas the Day, a home by RVA. This waterfront home is in the Country Club Shores and has a gorgeous open floor ...
From $4734 per night (USD)
Expedia
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VRBO
The Beach on Longboat Key #225 Resort by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...
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VRBO
From $212 per night (USD)
Expedia
Beachfront Bliss: 2/2 with Stunning Gulf Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Dolphin's Retreat, where you can experience the ultimate beachfront vacation! 🏡 Property Highlights: ✨ Bea ...
From $212 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Relaxing Beachside Retreat on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Newly Renovated!! Sunny southern exposure abounds from this charming 2 bedroom 2 bath get a way at Beachplace. This thi ...
From $356 per night (USD)
VRBO
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Expedia
Florida Getaway on Longboat Key: 2BR Wooded Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Embark on a retreat to our inviting two-bedroom, two-bath condo situated on the second level within a wooded paradise. I ...
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Expedia
From $400 per night (USD)
VRBO
Piece of Paradise
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located on a most welcoming friendly street. This house with 3 bedrooms & 3 full bathrooms sits on a canal with dock and ...
From $400 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Tiffany Plaza in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Longboat Key Gulf Front Vacation Rental! Enjoy fabulous views from almost every window in this 2 bed, 2 bath condo on th ...
From $259 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Adorable Gulf Front Studio, Private Beach, Originally Part of Starfish Motel
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Adorable hidden oasis in the heart of Longboat Key. Beachfront studio with spectacular views of the beach and Gulf of Me ...
From $256 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Beach Front Hidden Gem Steps to the Gulf and Sand
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Adorable hidden gem directly on the beach and Gulf of Mexico. Your own private beach with sun loungers and all the beach ...
From $330 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Beachfront Cozy Condo: Sand n Gulf Steps Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private oasis directly on Longboat Key beach and steps to the Gulf of Mexico. Fully equipped with all the essentials, co ...
From $322 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Charming Beach Front Studio Steps to the Sand and Gulf
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming hidden gem directly on Longboat Key Beach for a secluded getaway. Amazing views of the Gulf of Mexico, and just ...
From $224 per night (USD)
Expedia
From $252 per night (USD)
Expedia
Longboat Key Beach Bliss
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our serene 2-bedroom, 2-bathroom condo nestled right on the pristine shores of Longboat Key, Florida. With th ...
From $252 per night (USD)
Expedia
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Expedia
Beach lovers paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to our beautiful gated community on Longboat Key. With four heated swimming pools a fitness center, game room ,fi ...
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Expedia
From $265 per night (USD)
VRBO
Waterfront condo with pool, tennis court, fitness center, internet, W/D, & AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Island Breeze Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $265 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Sutton Place #102A Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathr ...
From $247 per night (USD)
Expedia
From $352 per night (USD)
VRBO
The Isla at Beachplace-Beachfront condo with 5-star amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Be one of our first guests at The Isla at Beachplace. This beautifully updated 4th floor unit, elevator access, is fille ...
From $352 per night (USD)
VRBO
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Expedia
Lovely condo on Longboat Key. Boutique resort with all amenities ocean to bay.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Last minute cancellation provides you with an opportunity for a fabulous vacation at a fraction of the normal price. 2 ...
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Expedia
From $237 per night (USD)
VRBO
Turquoise Gem 1st Floor no stairs Longboat Key FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private BEACH Access! *Designer Renovation* Single level/Ground Level, 4 minute Walk to Bright White Quartz Sand, Welcom ...
From $237 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Chic Longboat Key Retreat, 10 Min Walk to Beach & 2 Mins to Dining!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seven Palms Beach House by AMI Locals Home in Longboat Key, FL 34228 Welcome to Seven Palms Beach House! This three-bed ...
From $214 per night (USD)
Expedia
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VRBO
Arbomar #604: Beachfront 2BR / 2BA Luxury Condo on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience modern beachfront luxury at Arbomar #604 on Longboat Key, brought to you by RVA. Nestled mid-island on this b ...
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VRBO
From $250 per night (USD)
Expedia
Beach front newly renovated 2.5 bedroom condo with private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxury Longboat Key Condo – Fully Renovated (Dec 2024) & Steps from the beach (private access). Welcome to Sea Pines Co ...
From $250 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Fairway Bay #155 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fairway Bay Fifth-Floor Retreat: Unparalleled Sarasota Bay Views Offered by Florida Vacation Connections Experience ...
From $223 per night (USD)
VRBO
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Expedia
Beautiful 3 bedroom with views of the Beach of Longboat Key.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity ...
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Expedia
From $517 per night (USD)
VRBO
Direct Beachfront Condo Birds eye view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible ...
From $517 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Partial Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful unit on the 5th floor with lake/pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with ...
From $229 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Gulf Views & Cozy Comfort w Large Lanai Tern's Nest #22 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in this stunning Longboat Key condo, where every day starts with incredible water views and ends with ...
From $222 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Charming 2-bedroom condo steps from Beach, Library and Grocery on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Get ready to relax in this marvelous 2-bedroom condo in Longboat Key. This cozy retreat features 1 king bed and 2 queen ...
From $267 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Gorgeous Beachside Condo in superior Longboat Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. ...
From $367 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Unit #313 Sand Cay Beach Resort Pool and Garden
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $400 per night (USD)
Expedia
From $817 per night (USD)
VRBO
Coastal Elegance by FVC
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Coastal Elegance managed by Florida Vacation Connection! Experience unparalleled luxury in this magnificent ...
From $817 per night (USD)
VRBO
From $529 per night (USD)
Expedia
4-bedroom house on Longboat Key with private beach access only 150 yards away.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Make yourself at home in this large recently remodeled 4-bedroom 3 bathroom Longboat Key retreat with 1 king bed and 3 q ...
From $529 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Gulf-Access Waterfront Home Near the Beach in LBK: Penfield Paradise by RVA
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Discover a private slice of paradise on Longboat Key, where waterfront tranquility meets tropical luxury. This stunning ...
From $520 per night (USD)
VRBO
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Expedia
Sea Place #307 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to a serene coastal retreat at this stunning 2-bedroom, 2-bath, condo nestled in the sought-after Seaplace commun ...
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Expedia
From $152 per night (USD)
VRBO
Welcome to Blue Crane by Florida Vacation Connections
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blue Crane by Florida Vacation Connections: Your Eclectic Florida Getaway on one of Millar Bays Canals! Disc ...
From $152 per night (USD)
VRBO
From $615 per night (USD)
Expedia
Beachplace 8-601 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Coastal Elegance at Beachplace Penthouse Welcome to your dream beachfront retreat, where coastal living meet ...
From $615 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Completely Renovated, Brand New Furnishings, Beach Castle 21
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to Beach Castle Resort Unit 21 – Your Dream Getaway! This fully renovated, ground-floor beach condo blends moder ...
From $356 per night (USD)
VRBO
From $790 per night (USD)
Expedia
Islander Club #16N Premier Beachfront Condo-1st Floor & Ocean Views by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect vacation getaway at the Islander Club of Longboat Key! Islander Club #16N is a 2-bedroom, 2-bat ...
From $790 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Charming Longboat Key 3-bedroom house with 3 min walk to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the best of Longboat Key and Sarasota from our cozy 3 bedroom rental. Just down the road is beautiful St. Arman ...
From $208 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Waterfront w/Dock, Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BEACH, BOAT, BIKE, FISH, KAYAK, TV/SPORTS, ENTERTAINMENT, FOOD, RELAX & ENJOY! Nestled between the highly sought after A ...
From $147 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Steps from the Sand – Luxury Beach Condo with Pool Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Leave the snow behind and soak up the sun! This stunningly renovated 2-bedroom, 2-bathroom condo has everything you need ...
From $207 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Charming 2-bedroom condo with AC, fitness room in wonderful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Longboat Key, this condo is a dream. Guests will feel right at home with 2 bedrooms featuring 1 king bed and ...
From $463 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Beachfront Bliss on Longboat Key- Steps to the sand
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out your door and onto the sand—this beachfront gem on Longboat Key is the perfect escape for couples or solo trave ...
From $303 per night (USD)
VRBO
From $235 per night (USD)
Expedia
The Pink Pelican- 3 bedroom with pool and dock.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Pink Pelican – A Bright Key West-Style Retreat on Longboat Key Professionally Managed by Florida Vacation Connection ...
From $235 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Enjoy endless gulf views from this welcoming oceanfront condo on Longboat Key - Pearl On The Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, ...
From $289 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Sutton Place #101A Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. This spacious 2-bedroom, 2 ...
From $351 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Waterfront, Spa/Pool, Private Paradise on Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Paradise at the Harbour Villa Club #114! Enjoy the "Captains Quarters" end unit which boasts over 1500 sf of ...
From $305 per night (USD)
VRBO
From $2601 per night (USD)
Expedia
Longboat Key, FL 2bd, 2ba condo available, Dec’25 & Jan’26. Steps to the beach!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully and tastefully updated 2 bedroom, 2 bathroom 1076 sq. ft. condo, on Longboat Key Florida, is now available D ...
From $2601 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Buttonwood Cove 204B by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Buttonwood Cove 204B | Longboat Key, Florida Bayfront Beauty with Gulf Access – Your Ideal Island Retreat Welcome to Un ...
From $159 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Waterfront home with private pool, boat dock, & serene views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $385 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Coastal Living at Its Finest at Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to Beach Harbor Club on Longboat Key, where unforgettable experiences await! Start your day with a sunrise over S ...
From $145 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Stunning Waterfront Retreat in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to this stunning 2-bedroom, 2-bath residence on Longboat Key. - Expansive water views of the bayou an ...
From $176 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Longboat Key, FL Spectacular Full OceanView Beachfront First Floor 1 Bed 1 Bath
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Longboat Key is waiting for you at this 1-bedroom condo. This peaceful retreat offers all the essentials for a terrific ...
From $415 per night (USD)
VRBO
From $728 per night (USD)
Expedia
Beachfront Luxury with Spectacular Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Islands West 12F, a luxurious beachfront condo located in the prestigious and secure Islands West building on ...
From $728 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Charming 2-bedroom condo with WiFi and AC in beautiful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Longboat Key like a local in this 2-bedroom condo. This lovely property features 2 queen beds, AC, WiFi, heat ...
From $342 per night (USD)
VRBO
From $764 per night (USD)
Expedia
Villa Sereno Summary:
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summary: Welcome to the picture-perfect, social media dream that is Villa Sereno by LUXVP. This 5-bedroom, 4.5 bathroo ...
From $764 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Beachfront with Beautiful Views on Longboat Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: This inviting beachfront condo on Longboat Key offers comfortable living with stunning bay, golf course, and ci ...
From $487 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Stylish Longboat Key townhome minutes to beach - Ospreys Nest
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by G ...
From $237 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Inn on the Beach 6-203 by LUXVP
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: LUXVP is pleased to offer this tastefully decorated and spacious 642 sq ft studio overlooking Island Lagoon. F ...
From $276 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Beautiful Panoramic Gulf and Sunset Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
BEACH FRONT CONDO! NO STREET CROSSING! JUST STEPS TO THE WATER. BALCONY WITH GULF AND SUNSET VIEWS! WITH NEW BATHROOM AN ...
From $380 per night (USD)
Expedia

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Results: 911 Rentals