Seasonal / Short Term Rental on Longboat Key /
Vacation in one of the nations most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and tastefully decorated 2 bedroom, 2 bathroom condo is located on the 5th floor and offers expansive, light filled living spaces with panoramic views of Cranes Bayou and Buttonwood Harbor. The screened lanai stretches across the entire condo and is accessible from both bedrooms and the main living area, creating the perfect setting for morning coffee, sunset cocktails, or simply relaxing while taking in the waterfront scenery. The interior features luxury vinyl plank flooring throughout with no carpeting. The kitchen is well appointed with solid wood cabinetry, solid surface countertops, and a convenient breakfast bar. The spacious primary suite includes an en suite bathroom and a large closet, while an in unit washer and dryer provide added convenience. This property is truly a water lovers paradise, featuring private beach access, a dock ideal for boating, fishing, or launching a kayak, convenient kayak storage, and exceptional community amenities. Residents enjoy a crystal clear swimming pool, tennis and pickleball courts, a clubhouse with a full kitchen and lounge area, bike storage, and a barbecue area with outdoor dining options. The location places you just a short drive from the world class shopping and dining of St. Armands Circle and the arts, culture, museums, and entertainment found in Downtown Sarasota. The only Publix Super Markets on the island is conveniently located just one mile away, making grocery shopping quick and easy. Available starting March 1, 2026. DECEMBER APRIL $6500/month, the rest of the year $4400. Call today to reserve your next unforgettable Florida vacation. This community is governed by a homeowners' association (HOA). The HOA requires lease applicants to complete an application process, which may include application fees, background screening, and common area deposits. Please contact the agent for specific details regarding HOA requirements and associated fees for this property.
Seasonal / Short Term Rental on Longboat Key /
Vacation in one of the nations most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and tastefully decorated 2 bedroom, 2 bathroom condo is located on the 5th floor and offers expansive, light filled living spaces with panoramic views of Cranes Bayou and Buttonwood Harbor. The screened lanai stretches across the entire condo and is accessible from both bedrooms and the main living area, creating the perfect setting for morning coffee, sunset cocktails, or simply relaxing while taking in the waterfront scenery. The interior features luxury vinyl plank flooring throughout with no carpeting. The kitchen is well appointed with solid wood cabinetry, solid surface countertops, and a convenient breakfast bar. The spacious primary suite includes an en suite bathroom and a large closet, while an in unit washer and dryer provide added convenience. This property is truly a water lovers paradise, featuring private beach access, a dock ideal for boating, fishing, or launching a kayak, convenient kayak storage, and exceptional community amenities. Residents enjoy a crystal clear swimming pool, tennis and pickleball courts, a clubhouse with a full kitchen and lounge area, bike storage, and a barbecue area with outdoor dining options. The location places you just a short drive from the world class shopping and dining of St. Armands Circle and the arts, culture, museums, and entertainment found in Downtown Sarasota. The only Publix Super Markets on the island is conveniently located just one mile away, making grocery shopping quick and easy. Available starting March 1, 2026. DECEMBER APRIL $6500/month, the rest of the year $4400. Call today to reserve your next unforgettable Florida vacation. This community is governed by a homeowners' association (HOA). The HOA requires lease applicants to complete an application process, which may include application fees, background screening, and common area deposits. Please contact the agent for specific details regarding HOA requirements and associated fees for this property.
RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club Just steps from the Beach!
Start living the island lifestyle in this beautifully updated, furnished 2 bedr
2 bed, 2 bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach to bay communit
GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought after Bay Isles community. The spacious Kitchen had
Longboat key "seaplace" condominium located on the gulf side. 2 month minimum required. Season 2027 jan april $6,500/month. Booked for feb april 2026. Immaculate, turnkey furnished 2 bedrooms/2 bathro
STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium featu
Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is lo
Escape to paradise with a stay in this newly renovated 2 bedroom, 2 bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, thi
BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers s
Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if
AVAILABLE Dec. 2025 April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened bal
New Listings & Price Reduction Updates sent directly to your email
Create Your Own Property Search saved for your return visit.
"Like" Listings and Create a Favorites List
* NOTICE: By creating your free profile, you authorize us to send you periodic emails about new listings that match your saved searches and related real estate information.If you provide your telephone number, you are giving us permission to call you in response to this request, even if this phone number is in the State and/or National Do Not Call Registry.