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Vacation Rentals in Oldsmar, FL and nearby

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All 99 Rentals in the Oldsmar Area
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From
$500
Per Week
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1 / 7
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Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$93
Per Night
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1 / 6
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$5,180
Per Month
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1 / 19
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 4
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The following rentals are within 5 miles of Oldsmar, Florida.

From
$132
Per Night
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1 / 7
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Parking
  • Dryer
  • Stove
  • Microwave
  • TV
  • Air Conditioning
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here in a residential area. One block to the grocery and the trolley stops right in front to take you to St Armands... View all property information
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4 of 5 stars Reviewed September 15, 2014
We have stayed on Longboat Key several times but first time at Las Hermanas. This is a small 4 unit building. We stayed in unit 3. It is a well maintained and updated unit. It...
5 of 5 stars Reviewed August 8, 2014
We wanted to rent a place with an ocean view in a more relaxing (peaceful) place. We arrived to find our rental had a nice updated cottage feel. Plenty of things to do on Longboat...
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From
$105
Per Night
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1 / 7
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Longboat Key
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Washer
  • Grill
  • Microwave
  • Dryer
  • DVD Player
  • TV
  • Stove
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach. View all property information
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5 of 5 stars Reviewed January 21, 2015
Nicely decorated; comfy bed; updated bathroom; reasonably priced. A nice getaway. Great Publix supermarket just down the road.
5 of 5 stars Reviewed July 24, 2014
So close to the beach, exactly what I was looking for. The studio was cozy and clean, cutely furnished. We loved the outdoor shower and will definitely return again!
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From
$3,795
Per Week
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1 / 25
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Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Guest Count
  • Parking
  • Air Conditioning
  • Shared Outdoor Pool...
  • Internet Access
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This gracious home, with a pool and a private entrance to the beach, offers a lovely location on Longboat Key for all that the area has to offer. There is a nice sense of space with an open living room, kitchen and dining area. There are also two sitting areas that adjoin the bedrooms. The... View all property information
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From
$132
Per Night
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1 / 7
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Parking
  • Refrigerator
  • Ceiling Fans
  • VCR
  • Patio
  • Dryer
  • Washer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our... View all property information
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5 of 5 stars Reviewed December 10, 2014
The owners were great, the place safe,clean,equipped,location perfect for walking to dine, shop and enjoy Longboat Key! We will be back!
5 of 5 stars Reviewed September 28, 2014
Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
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From
$99
Per Night
View Details
1 / 18
Payment Protection
Longboat Key
Studio, 1 Bathroom, Sleeps 3
Bookings
Details Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Grill
  • Microwave
  • Washer
  • Patio
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This complex is a two story building with only 15 condos, 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, direct beautiful Ocean views. The ground floor studio features a... View all property information
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From
$5,180
Per Month
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1 / 5
Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • VCR
  • # Of Bathrooms
  • TV
  • Satellite TV
  • Refrigerator
  • DVD Player
  • Private Outdoor...
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Spectacular penthouse condo. Additional amenities include: coffee maker, laundry, ice maker. View all property information
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From
$120
Per Night
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1 / 25
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Microwave
  • Safe
  • TV
  • Dryer
  • Gym
  • Refrigerator
  • Washer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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From
$135
Per Night
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1 / 23
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Washer
  • Refrigerator
  • Safe
  • Parking
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Beach on Longboat Key - New Gulf Front Condo # 225 This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. A heated pool overlooks the Ocean. The pictures of the beach and Ocean views... View all property information
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From
$115
Per Night
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1 / 6
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Longboat Key
Studio, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • TV
  • Patio
  • Grill
  • Stove
  • DVD Player
  • Dryer
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
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From
$171
Per Night
View Details
1 / 29
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Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Dryer
  • Microwave
  • Stove
  • Parking
  • Grill
  • Dishwasher
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing. Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of... View all property information
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5 of 5 stars Reviewed July 13, 2014
We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
5 of 5 stars Reviewed July 9, 2014
Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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From
$157
Per Night
View Details
1 / 16
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Dryer
  • Patio
  • Stove
  • Parking
  • Refrigerator
  • Safe
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit... View all property information
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5 of 5 stars Reviewed November 27, 2014
Very clean appartment, well equipped kitchen for self catering, with all the kitchen utensils spotlessly clean, very good position on the beach. Quite and very peaceful. Would go...
5 of 5 stars Reviewed June 13, 2014
I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
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From
$1,650
Per Week
View Details
1 / 19
Longboat Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Hot Tub
  • Washer
  • Dishwasher
  • Refrigerator
  • Stove
  • Parking
  • Dryer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with... View all property information
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From
$1,800
Per Month
View Details
1 / 23
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Number Of Bedrooms
  • Internet Access
  • Ceiling Fans
  • # Of Bathrooms
  • Patio
  • Shared Outdoor Pool...
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort complex, you'll find all sorts of amenities just outside your door, or across the street on the... View all property information
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From
$4,000
Per Month
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1 / 26
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Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Terrace
  • Satellite TV
  • Parking
  • Air Conditioning
  • Shared Outdoor Pool...
  • Internet Access
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You'll enjoy the feel of an old-fashioned Florida beach vacation in this quiet, secluded 8-unit complex nestled on the shores of the Gulf of Mexico at the north end of Longboat Key. This is the definition of the simple life! Australian Pines whisper their invitation to stay and relax for a while.... View all property information
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From
$195
Per Night
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1 / 25
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Gym
  • Balcony
  • Parking
  • Shared Outdoor Pool...
  • # Of Bathrooms
  • Terrace
  • Air Conditioning
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is a beach lover's paradise. It offers full Gulf of Mexico views from the wall of sliding glass doors in the main living space and the open porch – ideal for relaxing with your morning coffee and throughout the day to your front row seat for the famous west coast sunsets. Recently... View all property information
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From
$3,000
Per Month
View Details
1 / 19
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Boat Available
  • Parking
  • Internet Access
  • Gym
  • Air Conditioning
  • Ceiling Fans
  • Garage
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on the beach relaxing in the sun, you couldn't pick a better spot. Close your eyes and imagine the sound of the wind whispering through the... View all property information
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From
$200
Per Night
View Details
1 / 8
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • Dryer
  • DVD Player
  • Air Conditioning
  • Ceiling Fans
  • Stereo System
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We have a two bedroom, comfortably furnished condo unit overlooking the Gulf of Mexico. Our favorite room is the lanai - a screened in porch area with dining table and sitting area, especially the views as the sun sets over the Gulf. We are located on the north end of Longboat Key - more secluded... View all property information
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5 of 5 stars Reviewed August 13, 2014
This place is AWESOME, we stayed in the 4 bedroom housebayview with the private pool. It was the perfect vacation. The only mishap was the AC in one of the small rooms stopped...
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From
$3,750
Per Month
View Details
1 / 24
Payment Protection
Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Parking
  • Boat Available
  • Air Conditioning
  • Grill
  • Garage
  • Balcony
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses. It's easy to see why people love to stay at this beautiful, sprawling resort. A friendly guard at the gate will welcome you into a lushly landscaped compound, and will direct you down a winding tree-lined... View all property information
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From
$192
Per Night
View Details
1 / 27
Payment Protection
Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Garage
  • Balcony
  • Satellite TV
  • Terrace
  • Shared Outdoor Pool...
  • Ceiling Fans
  • Air Conditioning
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
On beautiful Sarasota Bay in a lush tropical setting, Harbour Bay Club is on Dream Island, only a short walk to the famous beaches of Longboat Key. Comfortably and stylishly decorated, this condo offers stunning views of the Bay from both the living area and the master bedroom. There are two... View all property information
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From
$178
Per Night
View Details
1 / 25
Payment Protection
Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Make Inquiry
Amenities & Details
  • Terrace
  • Shared Outdoor Pool...
  • Boat Available
  • Air Conditioning
  • Guest Count
  • Parking
  • # Of Bathrooms
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a vacation filled with extras when you stay at this lovely 3 bedroom, 2 bath Buttonwood Harbour condominium. An attractive complex located at the south end of Longboat Key, Buttonwood Harbour offers a variety of amenities to suit the needs of every vacationer, beginning with a large, heated... View all property information
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From
$100
Per Night
View Details
1 / 21
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Longboat Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Air Conditioning
  • Number Of Bedrooms
  • Shared Outdoor Pool...
  • Satellite TV
  • Internet Access
  • Terrace
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This second story private mother in law apartment may just be the prettiest waterfront hideaway on Longboat Key. The owners spared no expense when they built this luxury addition to their home, wanting to give their guests the best possible resort experience. With hand-hewn hardwood floors, solid... View all property information
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From
$5,000
Per Month
View Details
1 / 10
Payment Protection
Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • TV
  • Garage
  • Washer
  • DVD Player
  • Parking
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious and beautiful 2 bedroom beach front property with spectular view of the gulf. Fully furnished with amenities that include pool and tennis courts. Conveniently located within walking minutes of shopping and shops. Within minutes of St. Armand's Circle. Premier location in Longboat... View all property information
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From
$110
Per Night
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1 / 25
Payment Protection
Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Terrace
  • Parking
  • Grill
  • Gym
  • Air Conditioning
  • Garage
  • Internet Access
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Will you be the lucky one to take advantage of this VERY RARE OPPORTUNITY to rent for the season at The Player's Club on Longboat Key. This gorgeous complex, featuring four mid-rise buildings facing the Gulf of Mexico, offers only a handful of rentals, most of which have been tenanted by the same... View all property information
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From
$193
Per Night
View Details
1 / 23
Payment Protection
Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stove
  • Hot Tub
  • DVD Player
  • Microwave
  • TV
  • Dryer
  • Refrigerator
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private boat dock and four lit tennis courts and WiFi access throughout the property. Watch the balcony bathe in the... View all property information
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5 of 5 stars Reviewed October 15, 2014
The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida...
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From
$179
Per Night
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1 / 14
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Washer
  • Dishwasher
  • Parking
  • DVD Player
  • Microwave
  • Grill
  • Safe
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
ENJOY this beautiful gulf front condominium located in The Cabana Beach Club of charming Longboat Key, just north of Sarasota. Longboat Key is a quiet, lushly landscaped barrier island with no neon or fast food restaurants. It is considered to be one of the Gulf Coast's most beautiful and desirable... View all property information
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5 of 5 stars Reviewed August 28, 2013
Well kept and well located condo in a small comfortable complex. Right on beach and you can enjoy sunsets from your screened in porch. Many nice updates in kitchen, bedroom and...
5 of 5 stars Reviewed January 11, 2013
My family (Mother, husband, 2 teenage children) stayed in unit 118 of this condo for a week. The unit is fabulous, well stocked and right on the beach - gorgeous views all day...
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From
$167
Per Night
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1 / 41
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Grill
  • Parking
  • Gym
  • TV
  • Safe
  • Microwave
  • Hot Tub
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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From
$2,303
Per Week
View Details
1 / 24
Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Terrace
  • Air Conditioning
  • Dryer
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beachfront resort, set on beautiful white sand beaches that meet the turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' Rate includes resort... View all property information
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From
$250
Per Night
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1 / 6
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Longboat Key
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Stove
  • Patio
  • Washer
  • Refrigerator
  • Dryer
  • Dishwasher
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
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From
$214
Per Night
View Details
1 / 6
Payment Protection
Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Washer
  • Stove
  • Microwave
  • Dryer
  • VCR
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
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$2,600
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
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$150
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Longboat Key
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Grill
  • TV
  • Patio
  • Dishwasher
  • Refrigerator
  • Microwave
  • Gym
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Secluded, elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace and 3 month minimum rental. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; with workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool.... View all property information
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5 of 5 stars Reviewed November 21, 2014
This is a beautiful condo with lovely furnishings and every resort amenity one could ask for. Lots of walk in closets, flat screens, Jacuzzi tub, large rooms and great views...
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$145
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
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Amenities & Details
  • DVD Player
  • Dishwasher
  • Ceiling Fans
  • Grill
  • Microwave
  • Air Conditioning
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every evening, having a cup... View all property information
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$165
Per Night
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Dishwasher
  • DVD Player
  • Stove
  • TV
  • Ceiling Fans
  • Microwave
  • Satellite TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
AwayToParadise com Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every... View all property information
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5 of 5 stars Reviewed January 6, 2015
The beach or the pool, it's all steps from the door. The place is well organized, clean, and beautiful. All basic necessities are there. Really enjoyable stay.
5 of 5 stars Reviewed September 18, 2014
My wife and I just came back from our best vacation ever! We have been to a lot of places in our life, but the Longboat Key is our #1 preference, it is heaven on earth! We loved...
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From
$1,800
Per Month
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • DVD Player
  • VCR
  • TV
  • Dryer
  • Stove
  • Grill
  • Washer
  • Pool Table
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Looking for a medium/long Stay for 2016 ! MINIMUM : 3 MONTHS My Condo is nicely renovated with 2 beds/2baths in Longboat key! Corner unit, Third floor with elevator Sunny with amazing views! Granite counter in the Kitchen, and the bathrooms Kitchen is well equipped with blenders, Nespresso... View all property information
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$4,000
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Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Refrigerator
  • Dishwasher
  • VCR
  • Grill
  • Stove
  • Washer
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful ground floor beachfront 3 bedroom 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed , en suite bathroom with two sinks, glass... View all property information
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From
$189
Per Night
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
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Amenities & Details
  • Ceiling Fans
  • Parking
  • TV
  • Microwave
  • Stove
  • Dryer
  • Grill
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
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From
$83
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
  • Refrigerator
  • Microwave
  • Sauna
  • Dryer
  • Washer
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Make this charming Beach Villa your seasonal escape!! Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex nestled between the Gulf Of Mexico and the Bay offers a fully equipped,... View all property information
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$142
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Longboat Key
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • DVD Player
  • TV
  • Dryer
  • Refrigerator
  • Patio
  • Microwave
  • Dishwasher
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
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$3,800
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Longboat Key
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Cute beach bungalow is the perfect compact pool home for those looking for a laid back feel in the quite Longboat Key Village. Just down the street to MarVista, and the Public boat ramp, and a short distance to the beach access this home is made for the water and beach enthusiast. Tastefully... View all property information
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4 of 5 stars Reviewed April 28, 2014
I stayed here with my husband and daughter. The location was great as it is close to the bay and ocean. The neighborhood is quiet with nice neighbors. The peacocks in the...
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$500
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Stove
  • TV
  • DVD Player
  • VCR
  • Dishwasher
  • Safe
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the north end of Longboat Key, there are plenty of restaurants, shopping and cultural activities nearby. Other amenities include a heated pool,... View all property information
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$1,400
Per Week
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Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Washer
  • Grill
  • Patio
  • Microwave
  • Refrigerator
  • TV
  • Garage
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
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 walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
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$195
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Longboat Key
Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Patio
  • Washer
  • Refrigerator
  • Stove
  • Dryer
  • Dishwasher
  • TV
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Club Suite : Longboat Key Club complex located on the beach , with view of golf course : newly furnished / turn key suite ,fully equipped kitchen ,king bed and sleeper sofa ,new flat screen tv /dvd ,cable ,elevator , a/c, washer /dryer , private lanai deck for entertaining , private parking ,... View all property information
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$5,000
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Microwave
  • Parking
  • DVD Player
  • Patio
  • Dryer
  • TV
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
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... View all property information
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From
$190
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Refrigerator
  • Stove
  • Stereo System
  • Washer
  • Ceiling Fans
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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From
$129
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Longboat Key
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
An oasis by the sea! Ernest Hemingway like red brick walkways lead you to your cottage as well as one of the prettiest beaches in Florida or a serene view of Sarasota Bay. This one bedroom cottage is equipped w/ all of the luxuries not normally seen at a beach place including granite top newly... View all property information
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$145
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Longboat Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Parking
  • Refrigerator
  • Fireplace
  • Stove
  • Microwave
  • Washer
  • Patio
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Our Villa is available in January and May or June. Doctor's hidden home with gorgeous views: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. FREE Wi-Fi & Cable TV Our Venetian / Mediterranean Villa is... View all property information
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From
$2,100
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1 / 15
Longboat Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Patio
  • Dishwasher
  • Garage
  • Stove
  • Parking
  • Microwave
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautifully and completely renovated in 2015, including all new furniture too! This wonderful St. Armand's home is situated on a large corner lot and has been lovingly updated from top to bottom. New bathrooms, new kitchen and appliances, new landscaping. All new furnishings and beautifully... View all property information
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