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597 rentals
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One-of-a-kind home right on the gulf of Mexi
92 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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ZILLI VILLA
16 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 10
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Luxury unit $149 2 days next Saturday& Sunday Private Island beach open
83 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Welcome back rate $175 Penthouse Superior decor private island beach open
135 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Beautiful Beach Views that will let you see 2020 in a whole new perspective
219 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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This unit is a wow $175 amazing decor private island beach open
58 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Unit #309 Enjoy great rates, just steps to the sandy beach!
76 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Zilli Tower 503
12 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Outrigger 9 Gulf Front first level walk out to the beach Oct-Nov $195 per night
77 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Last minute CXL $169 2 day min inquire with in private island beach open
50 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Hidden Bay/Beach Paradise
72 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat
66 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Zilli Ocean Front 101
11 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Breathtaking Beach Front Property Ground Floor Condo
85 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*
35 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
60 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World.
80 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Penthouse Condo with Awesome Views !
71 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Updated Beachfront Condo on the Gulf of Mexico
74 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Beachfront Condo With Balcony, View of the Gulf
77 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Love the Beach? Love tennis? The pool? Great family home with many amenities!
36 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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Unit #218 Sand Cay Beach Resort Gulf Front
41 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views
50 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Unit #208 Sand Cay Beach Resort Pool and Garden View
158 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Tranquil waterfront with heated pool, dock and walk to beach
36 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Beachcomber unit 303
36 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK
39 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
39 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Updated Beach Style Condo at Sand Cay with Great Ocean Views.
90 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Panoramic beach View and amazing Sunset.
56 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Beach view. Year around Balcony Sunsets.
49 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH
60 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor
27 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Bayfront Longboat Key House with Pool and Beach Access
27 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Unit #120 Sand Cay Beach Resort Gulf View
29 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Charming beach house on Longboat Key, with private pool&beach access, pool, pet
81 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean.
28 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Longboat Key Beachfront - Beautifully Updated with Prime Location
22 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach
39 reviews
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5
33 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean.
30 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Pet Friendly Longboat Key Condo with View of Gulf
77 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft
37 reviews
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view.
32 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~
22 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
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Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6
30 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~
25 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
47 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Beach is Open - Beachfront Villa on Serene Gulf of Mexico
31 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
42 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Frequently Asked Questions about Longboat Key
Do any holiday rentals in Longboat Key have a pool?
Yes, here are some popular holiday rentals in Longboat Key that have a pool:\n
\n
~ SUPER SPECIAL from $139/night ~ OCEAN FRONT DLX STUDIO
\n
~ BEACH FRONT APARTMENT ~
\n
Holiday Home Directly by Sea - Self Catering
\n
\n
See all holiday rentals with a pool in Longboat Key on Tripadvisor
Do any holiday rentals in Longboat Key have internet access?
Yes, here are some popular holiday rentals in Longboat Key that have internet access:\n
\n
~ SUPER SPECIAL from $139/night ~ OCEAN FRONT DLX STUDIO
\n
~ BEACH FRONT APARTMENT ~
\n
Holiday Home Directly by Sea - Self Catering
\n
\n
See all holiday rentals in Longboat Key on Tripadvisor
What are the best pet friendly rentals in Longboat Key?
The best pet friendly rentals in Longboat Key are:\n
\n
Fabulous Longboat Key - A Mermaids' Oasis 4 minute walk to beach!
\n
The Beach Nest
\n
~ SUPER SPECIAL from $139/night ~ OCEAN FRONT DLX STUDIO
\n
\n
See all pet friendly holiday rentals in Longboat Key on Tripadvisor
What are some great rentals in Longboat Key that are kid friendly?
Some of the most popular kid friendly rentals in Longboat Key are:\n
\n
~ SUPER SPECIAL from $139/night ~ OCEAN FRONT DLX STUDIO
\n
~ BEACH FRONT APARTMENT ~
\n
Holiday Home Directly by Sea - Self Catering
\n
\n
See all kid friendly holiday rentals in Longboat Key on Tripadvisor