Explore Stunning Holiday Homes in Longboat Key, FL

Beach and Pool Access Gulf Coast Villa with Balcony offers accommodations in Longboat Key, a 3-minute walk from Longboat Key Beach and 13 miles from John and Mable Ringling Museum of Art. This beachfront property offers access to a balcony and free Wifi. Sarasota Jungle Gardens is 12 miles from the villa. Featuring a terrace and sea views, the villa includes 1 bedroom, a living room, cable flat-screen TV, an equipped kitchen, and 1 bathroom with a shower. Towels and bed linen are offered in the villa. The property has an outdoor dining area. Guests at the villa can rejuvenate themselves at the spa and wellness center and outdoor swimming pool. The John and Mable Ringling Museum of Art is 13 miles from Beach and Pool Access Gulf Coast Villa with Balcony, while Sarasota International Convention Center is 14 miles from the property. Sarasota Bradenton International Airport is 14 miles away.

Pool • Guest Services • Private Beach • View • Oceanfront • Spa • Laundry • Parking • Security/Safety • Ocean View • Sports/Activities • Balcony/Terrace

Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacations, the house was completely redecorated and stocked to offer all the comforts of home to our VRBO guests. A cool, beachy palette welcomes you to sit back and relax. The Zilli Villa is part of the Zilli Collection each with the Zilli touch of amazing view, decor, ( not typical wicker furniture, silly beach artifacts,40 year old flooring, 1 size fits all look.) We call it upscale coastal. The properties are more of a resort, 5 star hotel feel.

This Villa is a two bedroom/two bathroom light-filled, ocean front home located just 13 steps to the sand and 60 yards to the water. The interior has been professionally decorated in a cool palette of ocean colors.
Highlights of this home:
· Complete privacy in this standalone home
· Two bedrooms: one has one king and bedroom two has 2 queen-sized beds
· Free high-speed wireless internet
· Three TVs with cable
· Gas fireplace
· Full sized stainless steel appliances in well stocked kitchen and pantry
· On-site full size washer/dryer
· Stereo system and DVD player
· Two sofa sleeper couches and one futon – property can sleep up to eight
· 40 feet of windows with hurricane shutters facing the Gulf
· Clean, well maintained lawn
· Master bedroom faces Gulf with small patio
· Both bathrooms have combination tub/showers
· Both bedrooms have flat screen TVs and Casablanca fans
· Free access to pool (with free use of beach towels) next door
· Ample storage
· Dining room seats up to 10
· Entire home is on one level, making it safe for little ones or elderly guests
. Multiple woman's touches, make up chair area, make up mirror
· Our beachside patio overlooks the Gulf of Mexico

You’ll find everything you need on-site from free WIFI to dishes, linens, towels and even a few extras you may need for your stay like puzzles and soap. The nearby pool has a covered grilling area with picnic table overlooking the beach. There's plenty of room for bikes, a bike trailer and/or several vehicles. Hope to see you soon at one of my beautiful vacation homes. All you need is your bathing suit and a toothbrush.

This resort is not a place of public accommodation as defined by the ADA and, therefore, does not meet the accessibility requirements of the ADA. That said, there are some accessible features at the facility. Please ask me specific questions to determine if this property would a good fit for your needs.

We also own 4 elegant upscale condos next door:
3510391 - Zilli Tower 503 is a 5th floor Penthouse
4649102 - Zilli Ocean Front 101 is a direct walk out
7900243 - Zilli Ocean Front 201 and 9070766 - Zilli Ocean Front 202 are individual condos that can be made into a suite for larger groups with a connecting door.

- "My husband, daughter, and I had a wonderful stay at Jim's property on Longboat Key. Jim is a class act and answered all my questions promptly and thoroughly. He also knows the area so well, and he had great suggestions for restaurants and other things to do. The home is literally steps from the beach, and the beach and its sunsets are remarkable. If you are looking for peace, quiet, and beauty then this is definitely the spot for you!" - "I wish I could summarize our stay with a few simple words, I cannot. The host, Jim Zili, with simply the best host we have ever had through VRBO or any other rental service. He was in communication with us the whole time in case we needed anything. If we called or texted, he immediately picked up or called back. He’s such a kind man with your best interest at heart as a guest. The house is stunning. The views are amazing, the people around you are friendly, we could not have asked for more. I implore you to rent this property. You will not regret it. You will want to go back year after year. I know we will!!!"

Heated Pool Access | Steps to Beach | Long-Term Renters Welcome

Add a little serenity to your next trip in the Sunshine State when you book this 1-bedroom, 1-bath oceanfront vacation rental! Situated in the Turtle Crawl Inn Resort, this bright, airy escape puts Longboat Key’s attractions at your fingertips. Enjoy a home-cooked dinner with a sunset view on the balcony after strolling along the white-sand beaches, exploring Sarasota hot spots, or unwinding by the gulf-front pool.

-- THE PROPERTY --

SLEEPING ARRANGEMENTS
- Bedroom: 2 queen beds
- Living Room: 1 queen sleeper sofa

RESORT PERKS
- Heated outdoor swimming pool w/ sundeck
- Private beach access
- Putting green, shuffleboard
- Gazebo w/ gas grill & dining tables
- Outdoor shower
- Coin laundry machines

VILLA AMENITIES
- 2 Smart TVs
- Dining table, dishes & flatware
- Open floor plan w/ coastal decor
- Screened-in balcony w/ 2 cafe tables
- Beach chairs/towels/umbrella

KITCHEN
- Electric stove, oven, microwave
- Drip coffee maker, toaster, hot water pot
- Cooking basics
- Trash bags/paper towels

GENERAL
- Free WiFi
- Central air conditioning
- Complimentary toiletries
- Hair dryer, iron/board
- Linens, towels

ACCESSIBILITY
- Single-story unit
- Stairs required for access

PARKING
- Community parking lot (1 vehicle with parking pass)

-- THE LOCATION --

- Located in Turtle Crawl Inn Resort with on-site beach access
- 6 miles to Mote Marine Laboratory & Aquarium
- 7 miles to Sarasota Pier
- 10-13 miles to Sarasota attractions: Marie Selby Botanical Gardens, Sarasota Jungle Gardens, The John and Mable Ringling Museum of Art
- 18 miles to Manatee Village Historical Park
- 13 miles to Sarasota-Bradenton International Airport & 53 miles to St. Pete–Clearwater International Airport

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

ADDITIONAL INFORMATION
- This single-story unit requires exterior stairs for access

- "Beautiful property! Very quaint." - "We loved this place. The location was great- quiet, private beach with chairs and umbrellas for use. The condo was clean and had everything we needed- even paper towel, trash bags, and dish soap. Beds and couch weren’t the comfiest but besides that our stay was perfect!! Would love to return." - "Nice peaceful, we enjoyed it. Had no issues." - "Cozy Condo and close to beach! Friendly Staff. Mattresses are really old and sunk when you get in bed."

Located in the heart of Longboat Key Gulf Key provides it’ guest with one of the best locations on the key. With two (2) amble bedrooms and baths, the emergence of beachy relaxation and a slight nod to an old world you and yours will awake refreshed and cozy down after sunset.

With a full kitchen and automatic icemaker (Cheers!), your day can prepare as desired! With a back patio to gather in the sunlight or bask in the dusk, there is space for you, to find solitude or engage with those your travel with!

The main living area prominently features a Ekorness Stressless Leach Couch and Love seat to catch up on your favorite book or grab a throw and five into a show or movie on the LG Oled 4k TV (w/Media Center).

Within two blocks of Gulf Key, you will find many national and regional stores (including but not limited to) Publix Super Market, CVS Drug Store, Bank of America, Chase Bank, Sun Trust, US Post Office, Public Library, Longboat Key Tennis Center, Longboat Nail Salon and Dry Cleaning.

World famous St. Armand s Circle which offers fine dining, shopping and entertainment is a 10-minute drive away.

The greater Sarasota area is home to Van Wezel Performing, Ringling Museum, McCurdy's Comedy Theatre and Humor Institute, Asolo Repertory Theater, Sarasota Opera, Mote Marine Laboratory & Aquarium and countless Farmer's Markets!

"We look forward to welcoming you to your home away from home and experience why we live in the area year round!"

- "We stayed in this lovely condo for the month of March, 2022. We found the condo just perfect for our needs. When we arrived we were greeted by Teresa, one of the owners, who showed us around, highlighting where things were, how things worked, making suggestions for restaurants and answering our questions about the area. She concluded the tour by presenting us with a “Welcome” gift basket of fresh fruit and invited us to call or text if we needed anything. The unit is pleasant and comfortable, tastefully furnished in a contemporary style and decorated with interesting artwork and accessories. The dining area overlooks the patio, which has with lounge chairs, a table, a grill and large, beautiful potted plants. The bougainvillea, hibiscus and birds of paradise were in bloom. The condo is centrally located to about anything we wanted, whether on Longboat Key, St. Armand’s Circle, Sarasota, or Anna Maria Island. The beach, very short walk away, is beautiful and to our pleasant surprise, was never crowded. The sunsets were a must see. We met a few of the neighbors, some renters like us, and some full-time residents. All were very friendly. We are hoping to return the next time we visit Longboat Key!"

Luxury living behind the gates of Longboat Key Club. Your private villa overlooks the Signature 5th hole of Longboat Key Club Blue Heron course and your private pool and hot tub. Your screened lanai offers beautiful outdoor space for morning coffee and evening grilling, dining and sunsets. Your spacious home away from home is across the street from the Corey's Landing community pool and hot tub and tennis courts and includes parking and access to the private Bay Isles Beach Club. Publix, CVS and many other options are nearby and a short drive over the bridge takes you to restaurants and shopping on St. Armand's Circle.
Inside you will enjoy spacious luxury of 3 bedrooms, 2.5 baths and large living/dining areas. The two car garage holds 2 bikes and pool toys for your enjoyment.
This is a wonderful home in a quiet neighborhood where you can enjoy all Sarasota and Longboat Key have to offer!
Guests must complete HOA application form and pay $100 application fee.
60. day minimum rental

- "I don't have enough adjectives and superlatives to describe the experience. This two-bedroom (+ office) was amazing for our family of 6 as we stayed in Sarasota for the month of July. The beautiful, quiet neighborhood of Bay Isles on Longboat Key runs adjacent to the golf course with walking paths to a marina. Tennis courts and a large, private pool are just across the street. The house itself is well designed, spacious, and very comfortable for our long stay. We cooked nearly every meal in the well-appointed kitchen or grilled on the covered lanai. Meals were enjoyed in the formal dining room, at the separate kitchen table or out on the lanai next to the pool. We would stay again at this property without hesitation. If you are looking for a slice of paradise on Longboat Key, which is just far enough away from Sarasota to feel special, but close enough for daily trips into town and excursions, this is your place."

Welcome to your private slice of paradise on the coveted Longboat Key.

Nestled beachfront, this two-bedroom villa offers barefoot luxury, breezy interiors, and a peaceful atmosphere that instantly slows the pace.

Whether you’re here for a family getaway, a quiet reset, or just to listen to the waves with coffee in hand, this sun-drenched retreat delivers serenity in every square inch.

This single-level villa is beautifully designed with a soft, coastal palette—think ocean blues, natural textures, and timeless whitewashed wood tones. Inside, the open-concept living and dining area is filled with light and laid-back elegance. Rattan details and beach-inspired accents give the home warmth and character without ever feeling overdone.

The kitchen is fully equipped for casual meals, post-beach snacks, and all the little moments in between. Whether you’re prepping pancakes or mixing margaritas, you’ll have everything you need.

There are two serene bedrooms—one with a king bed and the other with two doubles to accommodate up to six guests. The two bathrooms are clean, simple and stocked with all the essentials (yes, including fluffy white towels).

The private lanai opens directly to the pool, just steps from the sand. Enjoy your morning coffee in a quiet breeze, take an afternoon dip, or linger outside for sunset cocktails—every day here begins and ends with the ocean as your backdrop.

Bedding/Linens • Child Friendly • Other • Air Conditioner • Fireplace/Heating • Laundry • Security/Safety • Internet • Wellness Facilities

Available March 1 for monthly or long-term rental. Updated Listing-Just Renovated Ground Floor 2 bed/2 bath Villa with attached carport at Windward Bay. Pool, tennis, pickleball, shuffleboard, fitness center, and kayaking. Gulf beach directly across the street. Nearby parks, shopping and restaurants. New Photos coming.

Pet Friendly • Security/Safety • Bedding/Linens • Air Conditioner • Internet • Wellness Facilities • Child Friendly • Laundry • Fireplace/Heating

Welcome to your dream rental home, perfectly positioned amid the Harbourside Course of the prestigious Longboat Key Club! This stunning 3BD/2.5BA villa has been fully renovated and is ready for your next vacation! Revel in breathtaking views of the lush golf course and the vibrant Florida sunsets that paint the sky each evening.
Step inside to discover:

1 minute to Private Beach: Rental property offers access to private exclusive Bay Isle Beach Club with access along the Gulf of Mexico. Bike accessible along with plenty of parking!

Private Pool: Sliding doors from the open family room lead you to this relaxing outdoor space, ideal for soaking up the sun or hosting lively get-togethers.

5 minute drive to world class restaurants and shopping: Spend the day or night walking beautiful St. Armands Circle, or lovely downtown Sarasota.

Vaulted Ceilings & Skylights: Bask in an abundance of natural light and airy, open spaces.

Spacious Open Kitchen: A seamless blend of the Family Room and Kitchen, perfect for both intimate gatherings and grand entertaining.

Paved Drive & 2-Car Garage: Elegant and convenient!

The master suite is your private retreat, featuring a terrace walk-out where you can enjoy tranquil views and fresh air. Situated in a secure community of Harbour Circle, this home is nestled behind the exclusive gates of Bay Isles. Take advantage of your own private pool or use community pool and deeded beach access through the Bay Isles Beach Club, where you can walk the white sandy beaches of LBK or enjoy beachside BBQs, picnics, and spirited games of beach volleyball.

This renovated gem offers modern luxury and an unbeatable location—don't miss your chance to make it yours!

Parking • Internet • Wellness Facilities • Bedding/Linens • Air Conditioner • Laundry • Pool • Other • Smoking • Private Pool • Hot Tub • Tv