- Villa Casuarina
- Villas of Avignon
- Westchester
- Whitney Beach
- Windward Bay
- Arbomar
- Banyan Bay Club
- Bay Harbour
- Bay Isles
- Bay Isles, Harbour Oaks
- Bayport Beach & Tennis Club
- Beach Castle Resort
- Beach Harbor Club
- Beachcomber
- Beachcomber II
- Beachplace
- Cabana Beach Club
- Casa del Mar
- Castillian
- Cedars Tennis Resort
- Cedars West
- Club Longboat
- Covert II
- Covert III
- Diplomat
- Fairway Bay
- Grand Bay
- Inn on the Beach
- Islander Club
- Islands West
- La Playa
- Longbeach Condominiums
- Longboat Arms
- Longboat Bay Club
- Longboat Harbour
- Longboat Harbour Towers
- Longboat Key Club
- Longboat Key Towers
- Longboat Key Yacht & Tennis Mark I
- Longboat Key Yacht & Tennis Mark II
- Longboat Landing
- Longboat Terrace
- Neptune
- Outrigger Resort
- Pelican Harbour
- Pierre
- Portobello
- Private Homes
- Private Homes, Cannons By The Sea
- Private Homes, Conrad Beach
- Private Homes, Country Club Shores
- Private Homes, Hideaway Bay
- Private Homes, Laguna Yacht Village
- Private Homes, Longbeach Village
- Private Homes, Sleepy Lagoon
- Private Homes, Triton Cove
- Private Homes, Twin Shores
- Privateer
- Promenade
- Salty Acres
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Longboat Key Vacation Rentals Show this location only Back to top
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Secluded Beachfront on Serene Gulf of Mexico - July 20 - 27 Available
2BR+/2BA
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Sleeps 4-6
– Cabana Beach Club #55972
$1595- $2495/wk
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Walk to the Beach - Vintage Charm Bungalow on Longboat Key
3BR/2BA
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Sleeps 6
– Private Homes #414104
$185 - $225 per night 3-4 night min stay
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Luxury Gulf Front Condo, 2 Bed/Bathrooms, Heated Pool, Tennis Court, Free Wifi.
2BR/2BA
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Sleeps 2-5
– Other Longboat Key Properties #487577ha
$3600 - $6300 per month 28-30 night min stay
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Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
5BR/4.5BA
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Sleeps 10
– Private Homes #255046
$6500- $7850/wk
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Fine Living Relaxation and Enjoyment! Enjoy Pool, Beach and Sunsets
3BR/2BA
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Sleeps 10-12
– Private Homes, Sleepy Lagoon #447571
$286 - $400 per night 3-5 night min stay
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Hideaway Bay Exclusive Home – Platinum Waterfront Property.
3BR+/3BA
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Sleeps 10-12
– Private Homes, Hideaway Bay #375240
From $2,340/wk- $10,000/Mo
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Beachfront Property Longboat Key
2BR+/2BA
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Sleeps 6
– Other Longboat Key Properties #247170ha
$395 per night 2 night min stay
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Water Front Home, Beautifully Furnished, Surrounded by Gardens
3BR+/2BA
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Sleeps 6
– Private Homes #271887
$5000/mo $3000/2wks $1900/wk low season
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2 BR Longboat Key Gulf Front Beach Villa
2BR/2BA
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Sleeps 6
– Private Homes #147044
$899 - $1799/wk
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Stunning, 3 Bedroom Home with Pool, Dock, Waterfront
3BR+/2BA
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Sleeps 8-11
– Private Homes #131214
From $1500/wk - $4000/mo
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Luxurious Villa with Pool, Gourmet Kitchen & Wi-Fi!
3BR/3BA
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Sleeps 6
– Private Homes, Conrad Beach #327566
$2995- $3450/wk
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Rent the Historic and Famous Longboat Key Beach House Weekly.
3BR+/2BA
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Sleeps 6-8
– Private Homes #385183
From $2,500/wk to $3,850/wk
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Luxury Single Family Beach House (Movie Theatre and Gym)
3BR/4BA
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Sleeps 6-8
– Private Homes #465411
$4200 per week 7 night min stay
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Beautiful Ocean View Condos on Soft White Sandy Beach 2BR/2BA – Sleeps 6 – Sand Cay Beach #450275
Special offer Multiple Offers August 5-Labor Day Week
Jul 26, 2013 to Sep 6, 2013
as low as $159 per night,three night min -
Longboat Key Florida - Sand Cay Resort
2BR/2BA
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Sleeps 4-6
– Sand Cay Beach #443817
$204 - $279 per night 3 night min stay
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Beachplace: a Luxury Gated Beachfront Residence
2BR/2BA
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Sleeps 4
– Beachplace #437314
$3,500/mo - $6500/mo
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Beautiful Family and Pet Friendly Bay View Home
3BR/2BA
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Sleeps 8
– Private Homes #450941
Rates from $2600/2 wk - $4800/mo
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Direct Gulf Front Home W/ Private Heated Pool
3BR/2BA
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Sleeps 6
– Private Homes #437302
$2500- $3500 Weekly
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Top Floor with Breathtaking Views of the Beach
1BR/1BA
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Sleeps 2-4
– Other Longboat Key Properties #3510391ha
$267 per night 2 night min stay
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Longboat Key Townhouse
2BR/2BA
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Sleeps 4
– Seaplace #439029
$2066 - $4650/mo
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Inn on the Beach 3-007 Great Beachfront Property on Longboat Key!
2BR/1BA
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Sleeps 6
– Inn on the Beach #30806
$2250 - $3800 per week 7 night min stay
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'Castle-in-the-Sky' Near Beach and Tennis
4BR+/2BA
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Sleeps 8-10
– Cedars Tennis Resort #202380
$999-$2050/wk - $3500-$7000/mo
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New Beach Condo with Pool/Gulf Views, Short Stays, Specials, Free Wifi!!!
1BR/1BA
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Sleeps 4
– Silver Sands #92051
$130 - $250 per night
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600 Ft to Beach-Easy Walk to Pool, Dining, Shopping, Parks
2BR+/1BA
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Sleeps 4-6
– Private Homes #110144
$875- $1295/wk
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Slice of Heaven on the Beach
1BR/1BA
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Sleeps 2-4
– Beachcomber #45173
$840 - $1225 per week 7 night min stay
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Xceeds Ur Xpectation: Great Value:Rare June Week Open; August Open: Act Now
2BR+/2BA
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Sleeps 2-5
– Private Homes #201395
$295 - $300 per night 6 night min stay
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Spectacular Gulf Front Ground Floor End Unit - 75 Steps to Beach!
2BR+/2BA
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Sleeps 4-6
– Sand Cay Beach #87337
$222 -$304/nt - $1554 - $2127/wk
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Tropical Casa Del Mar Paradise (July Givaways - Just Ask!)
2BR+/2BA
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Sleeps 4-5
– Casa del Mar #29427
$1075-$1575/wk - $4145-$6280/mo
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Private Island Oasis -Just 650 Feet from Beach
1BR+/1BA
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Sleeps 4
– Private Homes #57059
$690-$1150/wk - $2300-$4080/mo
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Pet Friendly Plus View of Gulf - Longboat Key Condo
1BR+/1BA
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Sleeps 2-4
– Neptune #318356
$99 - $139 per night 3-7 night min stay
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Pet Friendly Condo Directly Across from Beach, Best Deal!
1BR+/1BA
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Sleeps 2-4
– Neptune #314469
$83 - $139 per night 1 night min stay
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Stunning Gulf-to-Bay Views 3 Bedroom, Gulf Front, Corner Unit
3BR/2.75BA
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Sleeps 4-6
– Castillian #43535
$5950- $6950/mo
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The Beachcomber at Longboat Key - Unit 408
2BR+/1BA
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Sleeps 4-6
– Beachcomber #62134
$175- $230 per night, 7 night minimum.
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Designers Elegant Tropical Paradise
2BR+/2BA
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Sleeps 6
– Private Homes #101671
$1650-$2200/wk - $6600-$8800/mo
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Longboat Key Luxury Home by the Beach
3BR+/3BA
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Sleeps 7-9
– Private Homes, Conrad Beach #120191
$2450 per week 7 night min stay
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Gulf Breezes, Soft Sand -Your Tranquil Beach Resort!
2BR+/2BA
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Sleeps 4-6
– Casa del Mar #48305
$1075-$1575/wk - $4145-$6280/mo
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Key West-Style Condominium - Boat Dockage Available
1BR+/1BA
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Sleeps 2-4
– Other Longboat Key Properties #55086
From$120/nt - $825- $1350/wk
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Beautifully Decorated Beachfront Condominium in Longboat Key!!
2BR+/2BA
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Sleeps 6
– Longbeach Condominiums #72238
$2500- $5000/mo
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Right on Beach - Miles of Unobstructed View up and Down Gulf
1BR+/1BA
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Sleeps 2-4
– Whitney Beach #25541
$3,200- $4600/mo
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Paradise Behind the Gates at Longboat Key
2BR/2BA
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Sleeps 4-6
– Longboat Key Towers #139911
$7500- $8000/mo
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Beautiful Bay Side Home with Pool, Large Spa and 60 Foot Dock
4BR/4BA
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Sleeps 8
– Private Homes #311002
$6000 - $9000 per month 30 night min stay
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Lovely Tranquil Gulf of Mexico Beach Front Condo.Great Rates!
1BR+/1BA
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Sleeps 2-4
– Silver Sands #210777
From $105/nt - $700/wk
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Gulffront Condo, Unobstructed Gulf View, Virtual Tour, Sunsets
1BR/1BA
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Sleeps 4
– Turtle Crawl Inn #300706
$1043-$2065/wkly $149-295/Ntly
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Private, Canal, Dock, Pool Share
2BR/1BA
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Sleeps 4
– Private Homes #54784
$775/wk - $1995- $2995/mo
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Just Another Day in Paradise
3BR+/2BA
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Sleeps 7
– Private Homes #282307
$1500/wk - $3500/mo
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Direct Beachfront - Beautiful Sunsets - Mid Longboat Key
2BR/1BA
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Sleeps 4-5
– Beachcomber #286705
$1225 - $1610 per week 7 night min stay
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Beachfront Condo with Direct Gulf Views - Corner Unit
2BR+/1BA
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Sleeps 4-6
– Beachcomber #280286
$1225 - $1610 per week 7 night min stay
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Direct Gulf Views - Sunny Beachfront Corner Condo Updated 2011
2BR+/2BA
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Sleeps 4-6
– Beachcomber #286908
$1260 - $1645 per week 7 night min stay
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Direct Beach Front Gulf View Condo - Brand New Renovation!
2BR+/2BA
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Sleeps 4-6
– Beachcomber #332024
$1260 - $1645 per week 7 night min stay
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Luxury Home on Canal with Bay View - Walk to Beach
5BR+/4BA
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Sleeps 12
– Private Homes #197856
$7000- $10,000/mo
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Spectacular Beach View, Heated Pool, Tennis Courts
2BR/2BA
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Sleeps 6-8
– Cedars West #478253
$225 per night 14 night min stay
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Summer Special -Affordable Beach Waterfront Condo Longboat Key, Fl
2BR/1BA
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Sleeps 4
– Other Longboat Key Properties #328805
$775.00 per week
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Beachfront Condo on the Beautiful Gulf of Mexico
2BR/2BA
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Sleeps 2-4
– Private Homes #295904
From $325/nt - $1300/wk - $4500/mo
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Sophisticated Natural Beauty
3BR/3BA
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Sleeps 6-8
– Bay Isles #326827
$7500/Mo
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Gulf Front Condo - Spectacular View
2BR+/2BA
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Sleeps 4-6
– Sand Cay Beach #330126
$1392-$1547- $2200/wk
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Penthouse Condo with Awesome Views!
2BR+/2BA
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Sleeps 4-6
– Sand Cay Beach #285016
$1500- $2020/wk
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Peace of Paradise
2BR+/2BA
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Sleeps 5
– Whitney Beach #196862
$3200- $3600/mo
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Beautifully Updated Ocean View Condo on Longboat Key!
2BR/2BA
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Sleeps 4
– Cedars West #296565
$2600-$3300/2 wks - $3500-$5400/mo
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Luxury Beachfront Condo W/Fabulous Views of the Gulf!
2BR/2BA
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Sleeps 6-8
– Islands West #479973
$2800 - $6000 per month 28-31 night min stay
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Longboat Key Direct Gulf Front, Top Floor
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #361160
$5500/mo
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Lux Bay Condo, Everything New, Discounts Available-Inquire
2BR/2BA
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Sleeps 4-6
– Bay Harbour #465964
$3600 - $4350 per month 30 night min stay
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Waterfront Country Club Shore with Private Dock/Davit & Pool
3BR/3BA
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Sleeps 6
– Private Homes, Country Club Shores #430076
$ 6,000- $ 8,500/month
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Most Luxurious Gated Condo Property on Longboat Key!
3BR+/4.5BA
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Sleeps 7-8
– Tangerine Bay Club #315575
$3800- $6800/mo
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Water Front Condo in Fantastic Longboat Key Location.
2BR/2BA
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Sleeps 4-6
– Bay Harbour #404351
$2000 - $4750/mo
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Exquisite 2BR/2BA Condo with Beach/Gulf View
2BR/2BA
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Sleeps 4-6
– Longboat Key Yacht & Tennis Mark II #420570
From $5000 to $6000/mo
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Longboat Key Resort Condo - Full Kitchen, Tennis, Dock, Bikes
2BR+/2BA
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Sleeps 6
– Longboat Bay Club #402384
$975 - $1,895/wk
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Immaculate/Updated Oceanview Condo-Family Friendly
2BR+/2BA
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Sleeps 4-6
– Sand Cay Beach #345006
1428- 1953/wk
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Fabulous Direct and Full Bay View. Only Steps to the Beach!
2BR+/2BA
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Sleeps 4-6
– Pelican Harbour #424812
From $2,000.00
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Completely Renovated Upscale Condo
2BR+/2BA
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Sleeps 4-6
– Promenade #431140
From $5000/mo.
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Sanctuary of Sun, Water and Relaxation
4BR/3BA
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Sleeps 8-10
– Private Homes, Country Club Shores #442476
$5000 - $8000/mo
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Luxury at its Finest! Beautiful Beachfront Condo,Amazing Views
2BR+/2BA
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Sleeps 4-6
– Beachplace #403679
From $4500- $8500
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1BR Gulf Front Condo
1BR/1BA
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Sleeps 4-6
– Diplomat #451983
$185 - $205 per night 2-5 night min stay
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Silver Sands #257
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190787ha
$175 - $295 per night
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Silver Sands #257a
1BR/1BA
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Sleeps 2
– Other Longboat Key Properties #3190788ha
$125 - $170 per night
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Tranquil Retreat, Heated Private Pool, Easy Walk to Beach, Bay
3BR/3BA
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Sleeps 6
– Private Homes, Longbeach Village #369929
From $1,250/wk; $2,250/2 wk; $3,500/mo
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Totally Renovated Beach Condo Directly on the Gulf of Mexico
2BR+/2BA
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Sleeps 4-6
– Cedars West #434795
$2600- $3300/2 weeks, $3500-$5400/1 month
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Gulfside Villa on North Longboat Key
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #101500
$805 per week 7 night min stay
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Elegant Sanctuary on Lbk Island W/Garden, Walk to Beach & Bay!
3BR+/2BA
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Sleeps 6-10
– Private Homes, Longbeach Village #314948
$150 - $200 per night 4-7 night min stay
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Beach Castle Resort at Longboat Key
2BR/2BA
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Sleeps 6-8
– Beach Castle Resort #431289
$170 to $295/night
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Longboat Key Gulf-Front Paradise Luxury Condominium
2BR+/2BA
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Sleeps 5-7
– Cabana Beach Club #92268
$195 - $265 per night 2 night min stay
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Charming Canal Home with Private Dock and Enclosed Pool
2BR+/2BA
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Sleeps 8
– Private Homes #406624
$1300 to $1700/wk ; $3700 to $5000/mo
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Beautiful Townhouse in Cedars Tennis Resort - Ask for Specials
2BR/2BA
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Sleeps 4-6
– Cedars Tennis Resort #11855
$950-$1900/wk - $3150-$5200/4 wks
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Beautiful & Well-Maintained Gulf Front Condo on Longboat Key
2BR/2BA
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Sleeps 4
– Longboat Terrace #87543
$2,850- $4,950/mo
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Beachfront Cottage - Paradise on the Gulf of Mexico
1BR+/1BA
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Sleeps 4
– Turtle Crawl Inn #201566
$155.00 to $274.00 per night
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A Gulf-Front Beach Lover's Dream
1BR+/1BA
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Sleeps 2-4
– Other Longboat Key Properties #67239
From $2800/mo
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Luxurious 3 Bedroom Condo on the Beach - Stay and Relax
3BR/2BA
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Sleeps 5-6
– Longboat Key Yacht & Tennis Mark II #352381
$5500/mo/ $2800/2weeks US
- 3 Bedroom/3bath Vacation Rental in Private Gated Community 3BR/3BA – Sleeps 6 – Other Longboat Key Properties #274679ha
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Platinum Private Ocean Front Home
3BR+/4BA
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Sleeps 6-8
– Private Homes, Sleepy Lagoon #357481
$3500 to $4000/wk
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1st Floor Home Away from Home - Steps to Beach - Pool
2BR+/2BA
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Sleeps 4-6
– Longbeach Condominiums #261225
$2500- $5000/mo
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White Sandy Beach - Direct Gulf Access- Last Minute Specials
2BR/2BA
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Sleeps 4-5
– Sand Cay Beach #337429
$1016- 1650/wk
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A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.
2BR+/1BA
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Sleeps 3-6
– Private Homes, Cannons By The Sea #248087
$1300- $2095/wk
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Bayfront Longboat Key House with Pool and Beach Access
3BR+/3BA
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Sleeps 6-8
– Private Homes #89812
$1300- $1800/wk
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Beachfront Condo Paradise - Contact Us for Short Stays - 25% Off
2BR+/2BA
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Sleeps 4-6
– Sand Cay Beach #334933
From $166/nt
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Luxury Appointed Gulf Front Condo - Building 8 - Unit #302
2BR/2BA
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Sleeps 4
– Beachplace #291219
$3,800-$8,200/mo , $2,500/week
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Gated Luxury in Gulfside Paridise
3BR/2BA
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Sleeps 6
– Seaplace #455787
$3500 to $4500 per month
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Beach Condo Gulf of Mexico
2BR/2BA
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Sleeps 5
– Privateer #320615
$3500- $5500/mo
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Beachfront Gulf Views
2BR+/2BA
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Sleeps 4-6
– Villa Casuarina #313917
From $1050/wk - $3000/mo
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2 Brdm 2 Bath Condo Steps to Beach in Rarely Avail G5 Bldg
2BR+/2BA
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Sleeps 7
– Seaplace #413009
$3000- 3500/MONTH
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Beautiful, Recently Renovated 2BR / 2b Gulf Front Condo.
2BR/2BA
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Sleeps 4-6
– Longboat Harbour Towers #446629
$5,000/month
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Newly Renovated Condo at Sand Cay Beach with Great Ocean Views
2BR/2BA
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Sleeps 6
– Sand Cay Beach #2053098ha
$170 - $220 per night
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Secluded Beachfront on Serene Gulf of Mexico - July 20 - 27 Available
2BR+/2BA
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Sleeps 4-6
– Cabana Beach Club #55972
Overview of Longboat Key Vacation Rentals
Enjoy Stunning Beauty with Longboat Key Vacation Rentals
Stunning beaches and golden sunsets await you when you enjoy Longboat Key vacation rentals. There is so much to do and see. Visit the snow white sands of Coquina Beach, which has free parking and public access or visit the only undeveloped beach in the 32 acres of Joan Durante Park, where you can watch birds or travel down one of the many nature trails. If you enjoy fishing then visit New Pass where you can take part in saltwater fishing or just enjoying one of the beautiful sunsets as you sit on the soft sand.
Catch Up on Cultural Activities with Longboat Key Condos
You don't have to miss out on culture and cultural activities when you visit Longboat Key condos. There are many art galleries, museums and entertainment such as ballet and opera. Visit Wyland Galleries or Exit Art in Sarasota, just a short drive away. Experience Circus Sarasota, the Sarasota Ballet of Florida or the Sarasota Opera. You can even enjoy dinner theater at Golden Apple Dinner Theater or take in a movie at Regal 20 Cinema Movielines.
Savor Local Cuisine with Southwest Florida Beach Rentals
Southwest Florida has plenty to offer when it comes to local cuisine and fine dining. You can enjoy a mouth watering dinner at the Lazy Lobster or dine dockside at Mar Vista Dockside Restaurant and Pub. If it's world class cuisine you're after then try out Maison Blanche Restaurant with unbelievable French food or Euphemia Haye Restaurant where they serve American, Continental and International dishes. If you and your family enjoy a home-cooked meal, why not try out a charter boat with deep-sea fishing so you can serve it right in your condo? Southwest Florida beach rentals allow you to experience all of the many flavors of Florida.