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Longboat Key Rentals

$3 BEDROOM PENTHOUSE \CRUISE SHIP\ VIEWS w\/DOUBLE BALCONY at Beachplace!$
From $785 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 $785 per night (USD)
VRBO
From $342 per night (USD)
Expedia
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 $342 per night (USD)
Expedia
From $214 per night (USD)
VRBO
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 $214 per night (USD)
VRBO
From $485 per night (USD)
Expedia
The Beach House on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Beach House! This luxurious bungalow offers the perfect taste of modern living and a “South Beach” lifest ...
From $485 per night (USD)
Expedia
From $286 per night (USD)
VRBO
BEAUTIFUL WATERFRONT CONDO AVAILABLE FOR SUMMER 2023
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful remodeled condo is in perfect condition and ready for you to move in! It offers amazing bay views from th ...
From $286 per night (USD)
VRBO
From $582 per night (USD)
Expedia
The Promenade
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
2400Sq/Ft area, charming with 3 lovelly beds and 3 full baths..Condo full of ameneties, concierge, heated pool, privite ...
From $582 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Cedars East #852 Townhome by RVA
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...
From $293 per night (USD)
VRBO
From $1101 per night (USD)
Expedia
Sunset Heaven | On St Armands Circle Water Views, Private Heated Pool & Spa!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to Sunset Heaven, the ultimate waterfront retreat on Lido Key. This magnificent 4-bedroom, 3-bathroom home offers ...
From $1101 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Portobello #204 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA welcomes you to Gulf front vacationing at Portobello. With amazing beach views, and classic beach style, unit #204 i ...
From $196 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Stunning 2 BR Condo views of the Gulf and Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This ...
From $253 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Penthouse level with Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from t ...
From $281 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Partial Beach View 3 Bedroom Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful beachview unit on the 2nd floor with lake view and Beach View. Hard to find beautifully appointed 3 bedroom, 2 ...
From $575 per night (USD)
Expedia
From $942 per night (USD)
VRBO
Lovely Pool Home on St. Armand's Circle, Sarasota
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
St. Armand's Circle, is home to this beautifully decorated 6 bedroom 4.5 bath vacation home (which includes a 1 bedroom/ ...
From $942 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Dolphin Tale #12 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA welcomes Dolphin Tale! This condo immerses you in the ultimate beach relaxation vibe. Wake up to a beautiful private ...
From $253 per night (USD)
Expedia
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Expedia
Your Dream Vacation Awaits 2BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
White sand and blue water - welcome to Longboat Key near Sarasota on the Gulf of Mexico. Our property is small with only ...
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Expedia
From $434 per night (USD)
Expedia
2BR Walk to the Beach Across the Street- Bay Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Longboat Key offers sandy beaches and a relaxed island lifestyle. Whether you're here for a tranquil getaway or seeking ...
From $434 per night (USD)
Expedia
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Expedia
Longboat Key Luxury ~ 1600 Sq Ft Condo with Stunning Bay Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
White sand and blue water - welcome to Longboat Key near Sarasota on the Gulf of Mexico. Our property is small with only ...
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Expedia
Click For Pricing
Expedia
Beach Bliss: Spacious Condo | Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
White sand and blue water - welcome to Longboat Key near Sarasota on the Gulf of Mexico. Our property is small with onl ...
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Expedia
Click For Pricing
Expedia
Contemporary Luxury: 1600 sq ft Condo | Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
White sand and blue water - welcome to Longboat Key near Sarasota on the Gulf of Mexico. Our property is small with on ...
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Expedia
Click For Pricing
Expedia
Coastal Chic: 1600 sq ft Condo | Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our spacious condo is a generous 1600+ sq. ft. and directly faces Crane's Bay. All our units are identical with 2 bedroo ...
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Expedia
Click For Pricing
Expedia
Longboat Key Treasure- Two Bedroom Bayfront condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
White sand and blue water - welcome to Longboat Key near Sarasota on the Gulf of Mexico. Our property is small with only ...
Click For Pricing
Expedia
From $391 per night (USD)
Expedia
2BR Condo Bay Views, Across from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious condo, located directly facing the beautiful Crane's Bay. Our units, all measuring over 1600 sq. ...
From $391 per night (USD)
Expedia
From $439 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 $439 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Gulf-Side Studio in Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our compact yet efficient studio condo features a convenient Murphy Bed with twin-sized mattresses that seamlessly conne ...
From $222 per night (USD)
Expedia
From $277 per night (USD)
VRBO
1BR 2Ba Condo- Longboat Key Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This one-bedroom, two-bathroom condo has everything you need for a memorable beach getaway. The bedroom features a queen ...
From $277 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Pool View 2BR Condo at Gulf Tides
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience charm and convenience in the two-bedroom bayside condo located across the street from the beach and features ...
From $351 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Private Balcony On the Beach-Gulf Front 2BR Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Imagine starting your day with a cup of coffee on your Gulf-front balcony, watching the waves roll in. Spend your day sp ...
From $494 per night (USD)
VRBO
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Expedia
Waterfront condo with pool, jacuzzi, dock, and tennis courts!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Key to Happiness by AMI Locals Home in Longboat Key, FL 34228 Welcome to Your Key to Happiness, a gorgeous, newly ...
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Expedia
From $377 per night (USD)
VRBO
Sea Twig #103 Condo 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 $377 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Beachfront! Gorgeous gulf views, stunning sunsets, high end condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come spend your winter at our wonderful piece of paradise! Direct beachfront, gorgeous sunsets from the large balcony ...
From $458 per night (USD)
VRBO
From $115 per night (USD)
VRBO
Bikini Top Cottage in the historic village of Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bikini Top Cottage sweet spot for couples. Tiny Home in a Cozy Island village. The bungalow is on an alley way that ...
From $115 per night (USD)
VRBO
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Expedia
Beautiful, private beach and remodeled coastal retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stunning ground floor condo with lanai and privacy garden at Bayport Beach and Tennis Club, designed by Tim Seibert, one ...
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Expedia
From $174 per night (USD)
VRBO
Partial Beach View 1 Bedroom + Den
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
This home located in the sought after Seaplace community has a very personal feel to it and has a balcony with a side vi ...
From $174 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Cedars East #507 Townhouse by RVA
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...
From $387 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Longboat Key, canal 2 bed 2 bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring ...
From $659 per night (USD)
VRBO
From $475 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 $475 per night (USD)
Expedia
From $397 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 $397 per night (USD)
VRBO
From $476 per night (USD)
Expedia
3brm elevated canal front pool home on North Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coconut Place: Your Canalfront Paradise! Prepare to be captivated by the stunning Coconut Place, a beautiful ...
From $476 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Beautiful Longboat Key Condo Surrounded by Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Immerse yourself in this beautiful 2 bedroom, 2 bathroom condo just steps away from one of the most beautiful beaches in ...
From $261 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Waterfront condo with Gulf views, pool, tennis, & deeded beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whitney Beach 149 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $222 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Bright, Updated 2 Bedroom Condo On Longboat Key by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed by FL Vacation Connection, this spacious unit is furnished with comfortable seating in the living ...
From $318 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Cozy private beach condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enj ...
From $209 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Steps from the Water with Spectacular Bay Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up every morning and have coffee from your front patio, just a few feet away from the water. Play a round of pickle ...
From $281 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Waterfront Longboat Key Retreat With Dream Views
Bedrooms:
3
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 $280 per night (USD)
Expedia
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Expedia
2BR Longboat Key Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
From $218 per night (USD)
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 ...
From $218 per night (USD)
Expedia
From $424 per night (USD)
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 ...
From $424 per night (USD)
VRBO
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Expedia
Longboat Key Gem: 1BR Pool View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Coastal Charm: 2BR Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
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
Click For Pricing
Expedia
Tranquil Oasis: 2BR Longboat Key Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
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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Expedia
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VRBO
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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VRBO
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Expedia
Seaside Luxury: 2BR Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Relaxation Awaits: 2BR Longboat Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
2BR Tranquil Oasis: Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
Click For Pricing
Expedia
$Longboat Key 2BR\/1Ba Bayside$
From $283 per night (USD)
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 ...
From $283 per night (USD)
VRBO
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Expedia
Bayside 2BR Villa on Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This two-bedroom, two-bath, bayside villa offers all the essentials needed for a vacation at the beach. The kitchen is w ...
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Expedia
From $436 per night (USD)
VRBO
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 ...
From $436 per night (USD)
VRBO
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Expedia
Gulfside 2 Bed 2 Bath Condo Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
From $564 per night (USD)
VRBO
Exquisite Views Gulf-Front 2 BR Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This two-bedroom, two-bath gulf front retreat is designed for a relaxing and unforgettable stay, complete with all the c ...
From $564 per night (USD)
VRBO
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Expedia
Gulf Front 2BR Condo Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
$\Longboat Key Bliss: Coastal Escape 2BR Pool View$
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Expedia
\"Longboat Key Bliss: Coastal Escape 2BR Pool View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Great Find! Gulfside 2 BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
White Sands Gulfside 2 BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Spectacular Views Gulf-Front 2 Bed Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
2BR Paradise Found: Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
2 BR Gulfside Condo Relaxing Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
From $483 per night (USD)
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 ...
From $483 per night (USD)
VRBO
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Expedia
White Sands 2 BR Gulfside Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Longboat Key Getaway: 2BR Beach Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Exquisite Views from this Gulf-Front 2BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Longboat Key Retreat: 2BR Coastal Living
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
Click For Pricing
Expedia
Welcome to White Sands-2BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set amongst beautiful, landscaped grounds and white soft sand, this property stretches from Sarasota Bay to the Gulf of ...
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Expedia
From $282 per night (USD)
VRBO
1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Step onto the porch and let the salty sea breeze surround you. Start your morning with coffee or unwind in the evening w ...
From $282 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Gulf Side 1BR Cottage, Steps to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy Longboat Key's iconic beach ambiance, complete with a tiki hut, straw roofs, and brick-paved walkways. The family- ...
From $292 per night (USD)
Expedia
From $384 per night (USD)
VRBO
2BR Cottage Bayside Time for Relaxation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape the daily hustle and embrace tranquility at this charming cottage with breathtaking bay views. The spacious main ...
From $384 per night (USD)
VRBO
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Expedia
Longboat Key Cottage Steps to Pool and Bay Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Little Gull Cottage, a charming retreat with a spacious main bedroom featuring a king bed for ultimate comfor ...
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Expedia
From $248 per night (USD)
VRBO
1BR Cottage Gulfside Steps to the Water
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Step onto your porch and immerse yourself in the quintessential beach vibes of Longboat Key. The tiki hut, straw roofs, ...
From $248 per night (USD)
VRBO
From $458 per night (USD)
Expedia
2BR Cottage Bayside Close to the Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Little Gull Cottage, where Cape Cod charm meets Longboat Key's natural beauty. This cozy retreat features a s ...
From $458 per night (USD)
Expedia
From $325 per night (USD)
VRBO
1BR Cottage Steps to the Soft Sands of Longboat Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Imagine starting your day with a leisurely stroll along the soft, sandy beach, followed by a relaxing break on the porch ...
From $325 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Charming Bayside 1BR Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the charm of this cottage, featuring a generously sized main bedroom with a king bed, providing a comfortable ...
From $292 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to the charm of yesteryear at Little Gull Cottage, your Gulf-front retreat on Longboat Key. This cozy cottage wel ...
From $412 per night (USD)
VRBO
From $564 per night (USD)
Expedia
2BR Gulf Front, Feel the Gulf Breezes on the Porch
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Gulf-Front Cottage! Step into your spacious retreat, featuring a primary bedroom with a comfortable kin ...
From $564 per night (USD)
Expedia
From $373 per night (USD)
VRBO
2BR Cottage Bayside of Property, Full Resort Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Longboat Key is a haven for wildlife lovers, where you might spot tortoises, egrets, wild parrots, and even the island’s ...
From $373 per night (USD)
VRBO
From $412 per night (USD)
Expedia
2BR Cottage Bay Views Bayside
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious retreat features a king bed in the main bedroom, ideal for recharging after a day of beach adventures. The ...
From $412 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Your Home Away from Home: Little Gull 4BR Cottage
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Situated bayside with breathtaking views, this four-bedroom cottage is the ideal spot for your Florida beach getaway. Th ...
From $425 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Relax and Recharge in this 1BR Cottage
Bedrooms:
1
Bathrooms:
2
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 $283 per night (USD)
Expedia
Click For Pricing
VRBO
3BR Cottage- Footsteps to the Sand
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Little Gull Cottage, your perfect Gulf Coast getaway steps from the warm Gulf waters. This charming 3-bedroom ...
Click For Pricing
VRBO
From $554 per night (USD)
Expedia
2BR Cottage Gulf Side of Property, Resort Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming cottage offers a serene retreat with a king bed and private ensuite in the main bedroom. The guest room fe ...
From $554 per night (USD)
Expedia
From $612 per night (USD)
VRBO
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 $612 per night (USD)
VRBO
Click For Pricing
Expedia
Private Longboat Key House on Water
Bedrooms:
6
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 ...
Click For Pricing
Expedia
From $359 per night (USD)
VRBO
Longboat Key water view condo *Pool & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Space Find your tropical escape in the Lionfish Longboat Condo, our two-bedroom / two-bath fully furnished 1000 sq.f ...
From $359 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Beach View Condo- Quiet & Secluded with Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
***Update 10/13/2024***: We were extremely fortunate that our condo did not suffer any damage during Hurricanes Helene a ...
From $658 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Steps from the beach on Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Charming, one-of-a-kind property in a boutique-like setting with only 11 other units. There is a beautiful, heated pool ...
From $158 per night (USD)
VRBO
From $5670 per night (USD)
Expedia
Seas the Day: Home on Longboat Key by RVA
Bedrooms:
4
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 $5670 per night (USD)
Expedia
$Water View, Hidden Gem 2BR\/2BA Condo - Longboat Key FL. NEW LISTING$
From $213 per night (USD)
VRBO
Water View, Hidden Gem 2BR\/2BA Condo - Longboat Key FL. NEW LISTING
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to the best island on the west coast of Florida…Longboat Key! This tranquil condo is a newly renovated one of ...
From $213 per night (USD)
VRBO
$Starfish Bungalow A. Steps to the beach 2\/1 Coastal paradise ! Large airy open layout, grill, wifi !$
From $259 per night (USD)
Expedia
Starfish Bungalow A. Steps to the beach 2\/1 Coastal paradise ! Large airy open layout, grill, wifi !
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The spacious bedroom has a larger screen TV and a ceiling fan. Full size washer and dryer in the property , makes longe ...
From $259 per night (USD)
Expedia
From $1095 per night (USD)
VRBO
Steps to the Beach! Private Pool, Rooftop Deck, Pet Friendly!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Coastal Horizons by Anna Maria Vacations Home in Bradenton Beach, FL Less than a 1-minute walk to the beaches of AMI H ...
From $1095 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Waterfront Getaway Island Villa at Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax or work remotely at our Waterfront Island Villa on LBK. Nestled 1 block from the beach & on Sarasota Bay, enjoy wa ...
From $187 per night (USD)
Expedia

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