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Holiday Rentals near Legacy Trail

Train Depot, Sarasota, Florida
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    Travellers to Sarasota are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 2,607 Rentals in Sarasota
    The MacGregor House is 1925 Old Florida elegance1 / 22
    (1)Excellent
    1.8 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Renovated 2 bedroom 2 bath accross the street from beautiful Siesta Key Beach.1 / 33
    (15)Excellent
    10.9 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cute Efficiency Apartment - nice neighborhood1 / 8
    (11)Very good
    1.7 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Sarasota Downtown All Inclusive Town house !!!1 / 31
    (2)Excellent
    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Walking distance from the Bay! Charming 2 Bedroom House, Fenced and Private1 / 11
    (3)Very good
    0.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Reviewed 30 March 2021
    Beautiful home! Wonderful place to relax after enjoying all the sight seeing. Within walking distance to bay. Friendly neighborhood. Mary Helen is a fantastic hostess and makes...
    Reviewed 3 March 2020
    The location is great. Close to beautiful downtown, the Marina and minutes from Siesta key, Lido Key and Longboat Key. Groceries less than 1 mile away. The family friendly home...
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    About this property
    Located in the Ringling Museum area. Very quiet and friendly neighborhood. Close to grocery store, pharmacy, liquor. 1 block to the bay - 6 miles from the Gulf of Mexico. Full kitchen, screened in porch, full yard completely fenced in. Great for a family getaway or large group. Sleeps 6...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Guest Cottage, clean, convenient and remodeled.1 / 10
    (12)Excellent
    0.3 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Pet friendly
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    Reviewed 1 January 2022
    Beautiful cottage in a beautiful neighborhood setting. We were fortunate enough to stay here with our dog Luna. The owner Sue Had thought of everything. We will tell everyone...
    Reviewed 2 May 2018
    Sue and Dawn have done an amazing job equipping their wonderful studio for a perfect family vacation. The grocery store was barely three minutes away and the kitchen had...
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    About this property
    This get away is located in the Ringling Museum area and is a perfect choice if you're seeking a great location. You'll enjoy a private fenced in yard with a pergola, lounge chairs etc. Walk, dog walk, jog, bike, skateboard! This is a great place for it all! We are located in a quiet community...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bathroom, Sleeps 2
    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Vista Hermosa Cabana - Enjoy the beach life here on the island!!!!1 / 21
    (5)Very good
    13.2 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Downtown Sarasota Townhouse in Historic Center !!!1 / 30
    (2)Very good
    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Spacious tropical retreat with Private Pool!1 / 45
    (4)Excellent
    11.1 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Sea Shell Cottage  Sleeps 4, 2Bed/1Bath, King Bed, 2 twin, Shared Salt Pool1 / 22
    (4)Excellent
    8.0 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    7.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    10.8 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Lido Key Sarasota Pool Side Condo, Steps from Beach, St Armands Circle.1 / 31
    (4)Excellent
    6.5 kilometres from Legacy Trail
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    4.7 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4.4 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Location! Location! Location!  Sarasota!!!1 / 29
    (4)Excellent
    4.7 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Tiny Coral Oasis- Tiny House that sleeps 6 comfortably & Free WiFi1 / 22
    (8)Very good
    12.5 kilometres from Legacy Trail
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gulf Gate Estates, Sarasota
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 bath Guesthouse suite with Private entrance.1 / 18
    (1)Excellent
    5.5 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    *** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!1 / 41
    (15)Excellent
    4.6 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Single family home on golf course with enclosed pool1 / 19
    (2)Average
    7.6 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    7.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tiny House Amy - near the beach with Free wifi!1 / 21
    (11)Very good
    12.3 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Cozy, comfy beach duplex1 / 26
    (26)Very good
    8.6 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Tiny House Flamingo- Cute and vibrant with Free WiFi1 / 17
    (4)Very good
    12.4 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gulf Gate Estates, Sarasota
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Tiny House Margarita - A bright and cheery choice that sleeps 61 / 14
    (5)Excellent
    12.3 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gulf Gate Estates, Sarasota
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Periwinkle House - Your home away from home - close to locals beach1 / 27
    (10)Excellent
    10.0 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Sarasota Paradise ..1 / 23
    (15)Very good
    11.1 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Beautiful Villa minutes from downtown Sarasota, Benderson, golfing, tennis &more1 / 13
    (2)Excellent
    5.8 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 bedroom-Sparkling Clean–near beaches & downtown1 / 24
    (12)Excellent
    5.9 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    7.7 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Vintage Main Street Loft Apartment1 / 11
    (9)Very good
    3.4 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    11.6 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    12.5 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    8.4 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BS 1304 - Siesta Key Condo - Walk to America's #1 Siesta Beach! Perfect for1 / 25
    (13)Very good
    11.1 kilometres from Legacy Trail
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Peace in Paradise - Premium, Tranquil, Gulf Front Perfection on Siesta Key!1 / 24
    (56)Very good
    16.1 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Tropical salt water private pool!!1 / 25
    (41)Excellent
    6.0 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Fabulous refurbished coastal pool home on Lido Key seconds from St. Armand's Cir1 / 31
    (9)Excellent
    6.1 kilometres from Legacy Trail
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Welcome to The Loft!  A chic, modern, and inviting oasis in downtown Sarasota!1 / 24
    (76)Excellent
    4.1 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Playalido Unit #1 Vacation Home, Is Beach Complex A Few Steps-from Lido Beach1 / 10
    (51)Very good
    6.5 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Siesta Key - Siesta Dunes - Deluxe Beachfront Condo with Gulf of Mexico Views1 / 30
    (29)Excellent
    12.2 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    11.1 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Immaculate, Ground Floor, Pool View Condo In The Meadows1 / 24
    (10)Very good
    8.5 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Palm Aire Condo, Golf course/Water views, 2nd floor, 1200 sqft, Fully Furnished1 / 22
    (30)Excellent
    7.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Waterfront Home near Siesta Key with a pool1 / 44
    (52)Excellent
    11.2 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Outdoor Pool (Unheated)
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Luxurious Beach Front Condo On Siesta Key1 / 23
    (34)Excellent
    12.9 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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