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Longboat Key Vacation Rentals, Homes and Condos for Rent

Book Your Longboat Key Florida Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.

We have partnered with a major provider for Vacation Rentals by Owner directly through Sarasota Vacation Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places To Rent in Longboat Key Florida.

Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome

Longboat Key Private vacation home Star 4.7 Star Review

*** Contact owner for current availability and discounts! ***

A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short 3 minutes walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. .......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat

Longboat Key Condo Star 4.9 Star Review

Your safety is our top priority.
This unit is professionally cleaned using EPA registered product to combat Covid-19. In addition the unit is sanitized using a fogging process that kills 99.99% of bacteria and viruses following CDC & Florida guidelines.

Enjoy this beautiful, renovated Gulf-front sunny unit with vaulted ceilings, spectacul.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Sea Grape Inn #5- BEACHFRONT Property

Longboat Key Apartment Star 5.0 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Beautifully remodeled and upgraded; .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


A couple’s retreat. Condo Nestled in quiet area. Walk to beach & shops.

Longboat Key Villa Star 5.0 Star Review

NEW LISTING!

Perfect place for a beach getaway! Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, shops, restaurant, mini market, bike rental shop and more. Nestled in a quiet are, perfect to relax or work remotely. We offer Super Fast 600MBPS internet!

Centrally located in Longboat key, condo features a ful.......read more

2 Bedroom(s)
1 Bath(s)


Vacation Home


Stunning sunset views; Beachfront condo on central Longboat Key

Longboat Key Condo Star 5.0 Star Review

Private Condo located on second floor at Tiffany Plaza on Longboat Key. Second floor accessible only by security code elevator or stairs requiring key. Our condo has two bedrooms, both with a king bed, and two full bathrooms. Private balcony overlooking Gulf of Mexico, can be accessed through living room or master bedroom.

Condo Association.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Luxury Condo located on Beachfront Property

Longboat Key Condo

We just purchased this condo and it will be ready for Rental in December 2022 . The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise........read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Longboat Key Condo Star 4.8 Star Review

Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key!

Magnificent renovated (January 2022) condo with an open 1,132 sq. ft. floor plan, 2 bedrooms, 2 full bathrooms, full kitchen, a large living and dining room as well as a separate sitting room with a queen sleeper sofa. Condo sleeps .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


ON the Beach, Covert II Condominium

Longboat Key Condo Star 4.6 Star Review

On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service within the US, 2 TV\'s with cable service, Wi-Fi high speed internet, Screened Gulf front Lanai with table and chairs for a great dining view. second floor unit near the elevator. Coin operated washer / dryer available on each floo.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Your Arrival To Paradise Awaits Bay to Beach Condo

Longboat Key Condo

A unique hidden gem. Our condo is an upscale, private and beautiful retreat. This 2 bed 2 bath condo has been totally updated. We have installed new stone flooring, fresh paint and new furnishings as well as all new stainless appliances and kitchen hardware and new full size washer and dryer. Our condo is kept super clean, and we promise you .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Newly Remodeled! Directly Across from Beach ~ Condo

Longboat Key Condo Star 4.9 Star Review

The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. The island has very little commercialization and there are no fast food chain, but yet still has all the conveniences wanted.

No crowds, only a peaceful and relaxing beach that will feel as if it is your piece of heaven. Th.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Home


UNIQUE LONGBOAT KEY OASIS!

Longboat Key Condo Star 5.0 Star Review

We are please to offer our lovely, artfully ornamented and spacious 2BR/2BA second floor unit on a Longboat Key. Functional and decorated with love and care throughout this gem is located in small condo community (only 7 units) and offers a tranquil environment with magnificent sunrise views of the Sarasota Bay. Freshly painted in a soothing beach-.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Gulf Beach Resort - B

Longboat Key Private vacation home

Unit Features: 1-bedroom, 1-bathroom unit in the Orange Building Layout Note: Please note, the front door to unit 245 opens into a bedroom space before proceeding into the living areas. We kindly ask guests to take this layout feature into consideration when making their travel selections. View: Pool/Gulf View Bedding: 1 King, Sleeper Sofa Resort F.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Newly Renovated Tree House Condo Across The Street to the Beach!

Longboat Key Condo

Enjoy the outdoor heated pool or take a 1 min stroll across the street to the Gulf of Mexico where our pristine beaches await your arrival! Newly Renovated home with all new appliances, bedding and more! We look forward to having you on Longboat Key!.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Awesome Winter Getaway-Four Winds Beach Resort condo on the Gulf of Mexico

Longboat Key Condo Star 4.7 Star Review

1 bedroom 1 bathroom full kitchen furnished condo at the beach. Offering 1, 2 or all 3 weeks beginning January 16 through February 6, 2021, check in and check out on each Saturday. All amenities included in room WIFI, cable TV, hot tub, heated pool, steps from the white sands of the Gulf of Mexico, tennis courts, shuffleboard, bicycles, grilling .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Beach Castle #1: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo Star 4.8 Star Review

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature.



The grounds her.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


1000 Ft of private Gulf of Mexico Beach

Longboat Key Condo

1000 Feet of private beach in this one of a kind north end Whitney Beach 1st floor condo. This is the only condo with a large outdoor living room and tropical gardens. Relax on the outdoor sofa and indulge in a glass of wine and a grilled filet while the fire pit and lighted palms give you ambiance. This renovated unit is walking distance to all.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Sea Grape Inn #7 - BEACHFRONT Property

Longboat Key Apartment Star 4.9 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 2-Twin Beds.
Situated in this idyllic resort comprised of eight un.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


client said view crazy Aug sale arrive 26- leave 31 had cancellation

Longboat Key Condo Star 4.9 Star Review

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifact.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Home


Inn on the Beach 1307

Longboat Key Condo Star 4.8 Star Review

PLEASE NOTE: From November 19, 2022 through April 22, there is a 7 night minimum, Saturday to Saturday Stay Only.
FL Vacation Connection looks forward to welcoming to this luxury beachfront getaway located on the southern tip of Longboat Key, tucked behind the gates of the Longboat Key Club and Resort, known for its private beaches and po.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


1st Floor Home Away from Home - Steps to Beach - Pool

Longboat Key Condo Star 5.0 Star Review

A very warm welcome to your beautiful, home away from home on this Island Paradise!

This gorgeous location is truly one of the most relaxing places on the planet, and we know that you are just going to love it!

With views of the gorgeous Gulf of Mexico from the living areas, Master Bedroom and Lanai of our fabulous first floor apartm.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Love the beach? Tennis? Swimming? This great family friendly retreat has it all!

Longboat Key Private vacation home Star 4.9 Star Review

Spacious 2400 square foot elevated home (there are 16 steps to enter and exit) featuring wide open floor plan with vaulted ceilings, huge living/kitchen/dining room.
Fully equipped kitchen featuring large single bowl stainless steel sink, huge quartz island work space, double oven and seating for four at the counter.
DISH T.V. and whole hom.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 9


Vacation Home


Cedars East #810: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 4

Longboat Key Private vacation home Star 5.0 Star Review

RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious townhomes that are perfect for families or couples. There is something to suit every mood at.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 7


Vacation Home


Beach Castle Resort #14: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 4.8 Star Review

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature.



The grounds her.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Beachcomber unit 401

Longboat Key Condo Star 5.0 Star Review

Our building is located on the beach, this unit has an ISLAND view.
Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.
Please note: We do not allow Sunday or holiday arrivals and require a 7 night min.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Spacious third floor condo with Gulf views, screened-in porch, and shared pool!

Longboat Key Condo

Key Gulf View 302

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

**This unit requires an HOA application and will perform a background check on the reservation holder**

Spread out and relax in this lavish Gulf side condo - you can see it.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Gulf Front, luxury condominium in beautiful Long Boat Key, FL

Longboat Key Condo Star 5.0 Star Review

Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upscale, direct waterfront, luxury condo. This 3rd floor unit has incredible unobstructed views of the gulf---- direct views from living area and both bedrooms. Our condo boasts a full length, gulf front screened lanai with sliding door.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Canal front cottage, walking distance to sandy Gulf

Longboat Key Private vacation home Star 5.0 Star Review

Comforts of home with a fully equipped kitchen and washer/dryer. New queen and XL twin beds. Bedding and sheets supplied. Enjoy local restaurants, white sand beaches and fish the canal, bay or Gulf........read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Home


Silver Sands #245: 1 BR / 1 BA Resort on Longboat Key, Sleeps 4

Longboat Key Condo Star 4.4 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Gulf Beach Resort - A

Longboat Key Private vacation home

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Silver Sands #232: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 4.6 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Silver Sands #239: 2 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo Star 4.8 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Home


Cedars East #607: 2 BR / 2 BA Townhome on Longboat Key by RVA, Sleeps 8

Longboat Key Private vacation home Star 5.0 Star Review

RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious town homes that are perfect for families or couples. There is something to suit every mood a.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Beach condo is steps to a beautiful pool, beach with stunning views of sunset.

Longboat Key Condo Star 5.0 Star Review

This property has two bedrooms, two baths, and opens onto a screened in lanai. It is newly renovated with an open kitchen, office, and living room with views of the ocean. It is fully stocked with everything you need for a peaceful stay at the beach........read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Sea Grape Inn #4- BEACHFRONT Property

Longboat Key Apartment Star 4.7 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.
A first floor 2 bedroom 2 bath condo that offers a view o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Standalone Unit at Little Gull Resort. Amazing Sarasota Bay View! Walk to Beach.

Longboat Key Condo Star 4.0 Star Review

In the middle of April, the Florida weather is warm, the ocean is cool and blue, and the beach is all yours. We are pleased to offer our beautiful 4-bedroom, second-story timeshare for week 16 of 2018 (April 21st to the 28th). Unit #16 at Little Gull Cottages has spectacular, unencumbered views of the Sarasota Bay and is only a five minute walk t.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Cedars East #519: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6

Longboat Key Private vacation home Star 5.0 Star Review

RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious town homes that are perfect for families or couples. There is something to suit every mood a.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Beautiful studio unit at resort, sleeps 4

Longboat Key Apartment

Gulf Tides of Longboat Key offers a number of recreational opportunities and a superb location near the cities of Tampa, Sarasota, and Fort Myers. At the resort\'s beach, you can enjoy all types of water activities. The resort features a lighted tennis court, heated outdoor pool, bikes, shuffleboard, and barbecue grills. Close by, both Sarasota and.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Silver Sands #241: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 4.6 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Inn on the Beach 2207

Longboat Key Condo Star 4.7 Star Review

Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area.

Our guests have access to the beautiful private beach, pool and hot tub area only. Resort amenities (golf, dining, tennis, room & maid service or fitness) are private and not includ.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental

Longboat Key Condo Star 5.0 Star Review

The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Whitney Beach #336: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 5.0 Star Review

RVA invites you to experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with next door shopping at Whitney Beach Plaza, this property offers this two-bedroom, two-bathroom spacious end unit villa. Imagine spending your days lounging by the community pool, enjoying a game of tennis, or sipp.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Silver Sands #255S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo Star 4.6 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


*** OCEAN FRONT SPECIAL *** From $99/night

Longboat Key Condo Star 4.6 Star Review

*** OCEAN FRONT SPECIAL *** From $99/night
.
Longboat Key - Ocean Front Condo
~ DIRECT BEACH FRONT CONDO ~
~
Beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get.
~
We offer the lowest rates in this resort c.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


NEW! Gulf Getaway w/ Porch + Direct Beach Access!

Longboat Key Condo Star 5.0 Star Review

Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in the Silver Sands Gulf Beach Resort. Boasting a fully equipped kitchen and nestled on the ground floor, this beach escape provides all of the essential comforts paired with convenience for a relaxing stay. Tee off at the green in the.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


LBK Getaway

Longboat Key Condo

Welcome to Paradise at LBK Getaway! Great opportunity to stay at an exquisite 2-bedroom, 2-bathroom villa style home in the coveted north end of Longboat Key. Just feet away from the crystal blue gulf water and beautiful pristine sandy beaches. Spend the day catching a wide variety of fish on the fishing piers or building sand castles in the sand. .......read more

Studio
4 Bath(s) Sleeps 5


Vacation Home


Beautiful Waterfront Estate! Private gated property. Deeded beach access.

Longboat Key Private vacation home Star 5.0 Star Review

This spacious 5 bedrooms, 4.5 bath in the heart of Longboat Key is ready to accommodate you on your dream Florida vacation. Enjoy your stay in this beautiful Mediterranean style home in a private gated estate newly renovated in mint condition.

Upstairs, there are three bedrooms and bathrooms and a media room. The first master bedroom suite .......read more

5 Bedroom(s)
5 Bath(s) Sleeps 10


Vacation Home


Amazing Beachfront 2B/2B in Longboat Key

Longboat Key Condo Star 4.8 Star Review

October and November 2021 are still available with Deep Discount Prices!

Wonderful Beachfront condo in magnificent Longboat key. You will Love the beautiful private Balcony with sensational beachfront views of turquoise Gulf waters. This unit is on the second floor with an elevator for easy access. Space is a roomy 1175 sqft with a full-.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Million Dollar View!

Longboat Key Condo

Enjoy what I call my ‘Million Dollar View’ of the turquoise Gulf of Mexico ocean and sugar white sand. This second story condo is located in the Longbeach complex on the north end of Longboat Key and is located in one of the buildings closest to the beach. Live serenely in this pristine location knowing that the party and fun of Anna Maria Isla.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Hidden Bay/Beach Paradise

Longboat Key Private vacation home Star 4.9 Star Review

Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis cou.......read more

4 Bedroom(s)
4 Bath(s)


Vacation Home


A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.

Longboat Key Cottage Star 4.6 Star Review

Beachfront cottage that is located directly on the Gulf of Mexico and the only thing that is between you and your beach front cottage, are sea oats, palm trees and sand dunes. We are a premier and private beach holiday spot. The property is secluded and private and you are assured a hassle free beach front holiday.

The cottage has a full kit.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Home


Spacious 2Bdrm Longboat Key Condo

Longboat Key Condo Star 5.0 Star Review

Paradise awaits in this beautiful 2 bedroom/2.5 bath condo in the heart of Longboat Key. Conveniently located near Sarasota, situated right on Gulf of Mexico Drive, you\'re a short walk to Longboat Key Beach or just a short drive to several other area beaches .There is also bay access on the rear of the property where you will find a small private.......read more

2 Bedroom(s)
3 Bath(s)


Vacation Home


Beautiful Longboat Key RESORT 2 bed/2 bath, Sleeps 6,Granite/Stainless Kitchen

Longboat Key Hotel resort

Longboat Bay Club provides vacation accommodations that include recreation and pampered relaxation. Take advantage of the peace and privacy of a smaller property with the amenities of a larger resort. You will have plenty of room for relaxing in our 1600+ sq. ft. condominiums, each with a washer/dryer inside for your convenience. Our units also boa.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Longboat Key Club!! Direct Beachfront!!

Longboat Key Condo Star 4.7 Star Review

Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maxim.......read more

1 Bedroom(s)
1 Bath(s)


Vacation Home


Right on beautiful Sarasota Bay !! BEAUTIFUL VIEWS 2/2!

Longboat Key Condo Star 5.0 Star Review

Want a beautiful view of the Sarasota Bay from a luxury condo on Longboat Key? This two bedroom second Floor unit with Tommy Bahama Inspired Décor is perfect for a peaceful getaway. This condo is perfect for couples or small families looking to get away from it all.
We hope you have the opportunity to enjoy some of the unique features of this b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)

Longboat Key Condo Star 4.9 Star Review

Sand Cay resort is open using the industries best practices and guidelines to ensure that all CDC sanitizing guidelines are carried out completely. Moving forward we will use only a EPA-registered product, qualified for use against against SARS-CoV-2, the novel coronavirus that causes COVID-19. This process takes about 45 minutes and we will be cha.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Escape and Relax! Enjoy the Sea Air, Private Beach, St. Armands and more...

Longboat Key Condo Star 4.9 Star Review

Contact us for special bookings on this Stunning one bedroom one bath unit with just a short walk to Longboat Key Beach(Across the Street). Come enjoy beautiful Sunsets and put your toes in the sand! This unit is equipped with a full kitchen and dining area made for entertaining. Whether you are looking to enjoy a home cooked meal or order in this .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Island Paradise: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 8

Longboat Key Private vacation home Star 4.0 Star Review

RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key\'s sunshine. This home offers privacy un-matched with a tropical caged pool area offering a heated hot tub and pool. This large home seems to never end, around every corner there is comfortable spot to sit and read a book or watch your favorite show o.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo Star 4.9 Star Review

RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambian.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Cozy Canal Condo w/ boat dock and walk to beach

Longboat Key Condo

Enjoy the complete island experience in this one bedroom, one bath, canal front condo, with a private boat dock (21\' total length). We\'re located on a quiet street just half block from Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserve.

Relax on your waterfront patio, perfec.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Home


Updated Beach Style Condo at Sand Cay with Great Ocean Views.

Longboat Key Condo Star 4.8 Star Review

Current COVID-19 situation:
The County restrictions include numerous cleaning and other requirements for your safety. Our own internal requirements meet or exceed what is required by the County/CDC. Please also note that our condo has its own separate entrance, there are no enclosed corridors or hallways to get to the unit, it is accessible by o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


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