Vacation Rentals By Owner In Longboat Key, FL

Beach Front Condo That Has It AllbrWonderful ground floor unit – walk right to the beach – no steps to deal with! Very private patio that makes you feel like you’re in your own backyard. Bright and well decorated, you will love this updated unit. Comfortably sleeps 6, with one king, two full, and a pull out couch.br• Stainless steel appliancesbr• Wash and dryer in unit (only available in first floor units)br• Flat screen TVs in living room and bedroomsbr• Very well stocked kitchen (check our reviews)br• Bedrooms are “extended” – this is special, as it adds 60sf in both bedrooms and only a few units are “extended”br• Beach chairs, umbrella, and toys providedbr• Free high speed internet and expanded cable TVbr• Patio table seats 6brThe Sand Cay Beach Resort is a quaint and quiet resort ideally located “mid-Key”, close to lots of shops, restaurants, activities and museums. In addition to the beautiful beach, Sand Cay has all the amenities a beach lover would seek…heated pool, shuffleboard, tennis/pickleball court, large outdoor barbeque grills to name a few. The buildings are maintained to a high standard, and we are pleased to have staff on-site seven days/week to assist you with any needs. brSand Cay is just a few miles from Mote Aquarium, St. Armand’s Circle, and the popular Bridge Street area in nearby Bradenton Beach on Anna Maria Island. Boat and bike rentals, kayak tours, parasailing, golf, fishing and so much more are all nearby – the friendly and helpful office staff can point you in the right direction. For meals, you can pick up groceries at a new and spacious Publix just down Gulf of Mexico Drive. Or dine out at a wide array of restaurants right on the Key, including a beach bar right next door at the Zota Beach Resort. Many acclaimed restaurants are on the Key (including, Dry Dock, Shore LBK, Harry’s and Mar Vista), and an abundance in Sarasota. End your day by watching simply remarkable sunsets over the Gulf. Many renters return year after year. brLongboat Key is a safe, quiet beach community. It is a very residential community compared to most beach front areas that can be crowded, congested, and noisy. Longboat is perfect for relaxing with friends and family. The beaches in this area rate as tops in the nation by numerous publications and our beach is no exception.

Unit #120 Sand Cay Beach Resort Gulf View

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$262.73

Paradise found! Gorgeous. Two bedroom, two full bathrooms. Open concept. Leather couches, luxurious bathrooms. Master has a large walk in closet. Private screened in porch. Sunsets from your back porch, toes in the sand in seconds. Linens and towels provided, fully equipped large kitchen with all stainless steel appliances. Large screen TV in family room, bedrooms also have a tv. Free WI-FI. Private laundry room with FULL SIZED energy efficient washer and dryer. Beautiful pool for residents only. Propane BBQ grill. Close to everything! Across from Harry’s, Lo key, Solarzano’s Pizza, and walking distance to Euphemia Haye! A few minute’s drive to St Armands Circle. Fall instantly in love with this hidden gem!brbr30 Day minimum. No pets per the association. Sorry :(

GULF FRONT, 1ST FLOOR, 2 Bedroom 2 Bath private gem!

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$168.6

This 2-bedroom, 2-bath condo offers stunning bayfront views and is located in the desirable Longboat Harbour community. Enjoy private beach access, a community pool, tennis and pickleball courts, and scenic walking paths along the canal. Close to top restaurants, shops, and St. Armands Circle, this is the perfect spot to experience the best of Sarasota.brExperience the epitome of coastal living in this beautifully appointed 2-bedroom, 2-bathroom condo, perfectly situated on the second floor in the highly sought-after Longboat Harbour community. This bayfront gem offers breathtaking views and private beach access just across Gulf of Mexico Drive, complete with a full beach pavilion for your convenience.brbrEnjoy seamless access to a range of amenities, including a community pool, tennis and pickleball courts, and scenic walking paths that meander along the canal—ideal for wildlife watching. Immerse yourself in the vibrant local scene with top-rated restaurants and boutique shops just moments away. Plus, you're only a short drive from the iconic St. Armands Circle and all the cultural delights Sarasota has to offer.brbrBook your stay with Florida Vacation Connection, the premier rental agent, and let us ensure you have an unforgettable experience in this stunning Longboat Harbour condo.brbrRRR - 00962.2024

Longboat Harbour Bay Front 2 BR / 2 BA by FVC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$137.27

Experience the perfect blend of relaxation and adventure at Whitney Beach 185 by FVC in Longboat Key. Nestled on the pristine shores of the Gulf of Mexico, this cozy one-bedroom rental offers a serene escape with modern amenities like free Wi-Fi, a fully equipped kitchen, and access to nearby attractions such as theme parks, museums, and eco-tourism sites. Whether you're here to soak up the sun, explore local wildlife, or dive into water sports, this charming retreat provides everything you need for an unforgettable stay.

Whitney Beach 185 by FVC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$329.69

Summary:brExperience refined coastal living in this beautifully renovated ground-floor 1-bedroom condo on Longboat Key. Enjoy direct beach access, panoramic Gulf views, and upscale interiors with a king suite, modern kitchen, and queen sleeper sofa. Relax on your private patio, unwind at the heated pool, and explore nearby fine dining and luxury activities. Perfect for seasonal guests seeking elegance, comfort, and convenience. Minimum 1-month rental. $125 application fee and association approval required.brRRR-00359.2023brbrGuest Access:brPrivate entrance. Keyless lock system. Open off street parking.brbrThe Neighborhood:brLocated on the northern region of Longboat Key, Whitney Beach III is located beachfront and offers low rise 2 story buildings. Off-street parking, tennis court, beachfront pool all enhance the island lifestyle.

Gulffront Elegance | Renovated 1BR Condo w/ Direct Beach Access & Sunset Views

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$309.62

Step out your door and onto the sand—this beachfront gem on Longboat Key is the perfect escape for couples or solo travelers seeking sunshine, serenity, and style.brbrUnit 104 is a charming 1-bedroom, 1-bath condo located directly on the beach, offering stunning Gulf views and immediate access to the warm turquoise waters. Wake up to the sound of waves, take your morning coffee to the shore, and spend your evenings watching unforgettable sunsets just steps from your patio.brbrInside, you’ll find a thoughtfully designed space with modern coastal flair. The full-size kitchen features stainless steel appliances and granite countertops—perfect for cooking in after a day on the beach. The unit also includes WiFi, air conditioning, heating, and essentials like an iron and hair dryer. Laundry is made easy with on-site community coin-operated washer and dryer facilities.brbrThe Beach on Longboat Key is a peaceful, well-maintained resort that offers everything you need for a relaxing stay, including a heated pool, private beach access, complimentary lounge chairs and umbrellas, an outdoor shower, picnic area, free parking, and a welcoming on-site office.brbrWhether you’re planning a romantic getaway, a quiet work-from-paradise retreat, or a week of beachside relaxation, Unit 104 offers unbeatable comfort and location—a true gem right on the Gulf.

Beachfront Bliss on Longboat Key- Steps to the sand

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$211.57

Villa is 15 steps from your own private sugar sand bay beach. Cedars East Resort is a unique vacation getaway nestled within palms and mangrove trees. Enjoy the walk to the pool along cedar plank walking paths throughout the property. Canals and a bay side fishing dock enhance the tropical feeling of this beautiful setting.brbrWith the townhouse setting there is a feeling of privacy and “elbow room” missing at other tightly packed facilities. There is a spacious one-car enclosed garage and plenty of guest parking. This unit is steps away from the mini bay beach where you can launch a kaiak, lounge on a raft, or wade in the crystal clear bay water. Nearby are nature paths and a 32 acre nature preserve with walking trails.brbrFresh accessories, new windows and fresh paint were added in late 2020, and furnished with the help of a professional designer. Newer queen sleeper sofa, love seat, and overstuffed chair in living area with 9 foot ceilings give a spacious, comfortable feel. Our accessories give it a warm, inviting atmosphere: HD TV with Netflux and YouTube TV in living area and bith befrooms. The large great room, dining room, and kitchen are on the main floor along with a half bath. Upstairs there is a large master bedroom with king-sized bed, private bath, and double vanities. The guest bedroom has twin beds with a full bath next door. Sofa in living room converts to a queen bed. A screened lanai with a small bay view is a great place for breakfast in the mornings. Come and enjoy a setting that is family-friendly as well as intimate. Full size washer and dryer near bedrooms. Brand new this season: Fluffy white towels in the master bath and thick coral towels in the second full bath. 4 oversized beach towels new too.brbrArea is perfect for cycling and you'll see many cyclists on the roads and walkways. A bike rental shop is nearby. brbrKeywords: Three story townhouse; only two units per building give privacy, lots of natural light and extra quietness. Enclosed large garage and storage on ground floor; screened lanai off second floor living area; bedrooms on third level. steps to bay beach, 8 min to St. Armand's, close to Anna Marie Island, near down town Sarasota, next key down is Siesta Key Beach, Must visit Ringling Museum (free on Mon) voted Fla #1 attraction. Jungle Garden and Mote Marina also fun for kids. Great shopping /restaurants at St. Armand's circle, and down town Sarasota.

Country Club Long Boat Key Beach Villa 2B 3BA Pool

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$581.95

2400Sq/Ft area, charming with 3 lovelly beds and 3 full baths..Condo full of ameneties, concierge, heated pool, privite beach access, 24 hs gate guard, close to St Armand's Cirle, Airpoirt and major hwys.

Apartment

The Promenade

Longboat Key, Florida, United States

3

Bed

3

Bath

$126.68

Buttonwood Cove 204B | Longboat Key, FloridabrBayfront Beauty with Gulf Access – Your Ideal Island RetreatbrbrWelcome to Unit 204B at Buttonwood Cove—an elegantly renovated, first-floor condo offering breathtaking bay views and all the charm of traditional coastal living. This spacious 2-bedroom, 2-bath residence invites you to unwind in style, with a glass-enclosed lanai that extends your living space and provides a front-row seat to unforgettable sunrises and the serene sights of native sea life.brbrSituated on the narrowest part of Longboat Key, Buttonwood Cove is a true Gulf-to-Bay community. Enjoy direct access to 500 feet of private beach just across the street, complete with tiki hut, picnic tables, and lounge chairs—perfect for soaking in the sun or gathering for sunset cocktails.brbrProfessionally managed by Florida Vacation Connection, this beautifully updated condo boasts a bright and open floor plan, sophisticated yet comfortable furnishings, and a fully equipped, designer kitchen that makes cooking a joy.brbrThe primary suite features a king-sized bed, a walk-in shower, and private access to the lanai, where morning coffee meets spectacular water views. The guest bedroom is perfect for family or friends with two double beds and access to a nearby full bath.brbrCommunity amenities include:br-Heated poolbr-Tennis and pickleball courtsbr-Fishing pierbr-Kayak and canoe launchbr-BBQ/picnic areabr-Elevatorsbr-Covered under-building parkingbrbrWhether you're enjoying the sunrise over the bay or gathering for a sunset toast on the Gulf, this location offers the very best of island life.brbrPlease Note:br-One-month minimum rentalbr-No pets, no smokingbr-Condo association approval requiredbrbrRRR-01285.2025

Buttonwood Cove 204B by FVC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$297.26

The Pink Pelican – A Bright Key West-Style Retreat on Longboat KeybrProfessionally Managed by Florida Vacation ConnectionbrbrWelcome to The Pink Pelican, your dream island getaway on the north end of Longboat Key—just steps from the soft white sand and tucked along a peaceful bayou near Longboat Pass. This vibrant, Key West-style home offers the perfect blend of tropical charm, comfort, and convenience for an unforgettable beach vacation.brbrSet across from one of the island’s most beautiful and secluded stretches of beach, this three-story retreat features coastal décor, modern furnishings, and thoughtful amenities throughout. You'll enjoy two garages, a private dock for boating or paddleboarding, and a screened-in pool and lanai—ideal for lounging, entertaining, or cooling off in the Florida sunshine.brbrThe main living area on the second floor boasts an open-concept layout with a bright and cheerful kitchen, a breakfast bar for six, a spacious dining area, and a comfortable living room filled with natural light. Two guest bedrooms and two-and-a-half bathrooms are located on this level as well.brbrHead up to the third floor and discover the private master suite, accessible via a charming spiral staircase or your own private elevator. This spacious sanctuary features a king-sized bed, a luxurious en-suite bath with dual vanities, a walk-in shower, and a relaxing garden tub. Step outside to your private sun deck under a pergola—the perfect spot for your morning coffee or sunset cocktail.brbrWhether you're soaking up the views from one of the balconies, floating in the pool, walking to the beach, or watching wildlife from the dock, The Pink Pelican makes it easy to embrace the laid-back luxury of island life. Dolphins, manatees, and a variety of coastal birds are frequent visitors in this tranquil setting.brbrLocated on Florida’s Gulf Coast just outside Sarasota and an hour south of Tampa, Longboat Key is known for its pristine beaches, fine dining, and relaxed sophistication. You’ll be just minutes from the boutique shops and restaurants of St. Armands Circle, and within easy driving distance of cultural attractions, galleries, live theater, and even theme parks like Busch Gardens (1 hour) and Disney World (2.5 hours).brbrProfessionally managed by Florida Vacation Connection, you can rest easy knowing your stay will be seamless from start to finish. Your perfect island escape begins at The Pink Pelican—where sunsets, serenity, and seaside memories await.brbrRRR-01284.2025

The Pink Pelican- 3 bedroom with pool and dock.

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$302.8

From the moment you walk in the door of this 2 1/2 bedroom, 2 bath beach front condo you will know you made the right choice for your beach escape. Remodeled from the studs in 2019, this unit was transformed into this high quality, coastal retreat and is unlike any other condo on the Key. So much attention to detail in this beach condo shows up in every room. brViews: Breathtaking views of the Sarasota Gulf waters with its ever changing spectrum of blues. Located on the 4th floor of Tiffany Plaza Condominiums in the center of 7 mile Longboat Key, known for it's white sand and clear blue water. brKitchen: So perfect that you might actually want to cook while you’re on vacation! Most every kitchen appliance, tool and cookware is stocked. brLiving: Large living room with comfy new furniture and plenty of space to pull up more chairs when you you need to. brDining: The dining table has 4 larger chairs. But can seat 6-8 with the leaf added. The four barstools add additional seating at the island. brMaster: Wake to beautiful views of the water from 2 walls of the Master bedroom. Sliding doors open to the balcony. brBaths: Completely and thoughtfully updated baths with high quality finish out.brGuest Bedroom: Quiet queen bedroom with dresser, club chair and TV. brFlex Room: Flexible room with sleeper sofa, flat screen TV, desk, printer and wine fridge. brBalcony: Looking for a good spot to watch the sunsets with a cocktail or have your coffee every morning This is sure to be your favorite with its L-shaped sofa and Bistro table overlooking the blue green waters of the Gulf. brbrPool: Heated pool on the South side of Tiffany Plaza. brbrBeach storage: Tiffany Plaza has a beach side hut for short term storage of your beach chairs and umbrellas. brbrThe Beach: Longboat Key has 7 miles on each side of the island to walk, explore, fish and relax with arguably the most beautiful waters and sunsets in the world. brbrLocation: Longboat Key is conveniently located between Sarasota/St Armands Circle and Anna Marie Island and is known for its miles of white sand beaches, blue green Gulf waters, and breathtaking sunsets. Pickup Pickleball games are appx. .3 miles away every morning at Bayfront Park. Bicycles can be rented at Ace Hardware next to the park. brbrProvided with the condo: brBath and beach towels, bed linens, hairdryers, one full size shampoo, conditioner, body wash and hand soap provided per stay in each bathroom. Starter pods for the Kurig coffee maker, dishwasher and washing machine. Starter dish soap, paper towels and toilet paper. brMost every kitchen appliance, tool, cookware and dishware is stocked, so please ask us if you would like to know if we have a specific item. brbrOptional Services: br- Order groceries, beer and wine to be delivered upon your arrival from the Publix grocery store on the island so your vacation can begin immediately upon your arrival! br- Add on weekly or mid month housekeeping for $150-$200/cleaning. brbrTreat yourselves to a stay at this fresh, new beach condo and you will want to make it your home away from home year after year. brbrPLEASE NOTE: br- Message us through VRBO for more information on length of stay. br- Renters will need to sign a rental agreement with the property owners and provide info and a $1000 refundable damage deposit to the Tiffany Plaza HOA for the common areas.br- Search 3 Palms by the Beach LBK on Google Maps for more info.

Gorgeous Gulf views and a beachfront location!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$333.42

Our building is located on the beach, this unit has an ISLAND view.br br Relax and Enjoy the Beach, Pool & Longboat Key! New Kitchen! Shopping Nearby! br br Please note: We do not allow Sunday or holiday arrivals and require a 7 night minimum stay.br br Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.br br About the Propertybr br br One Bedroom Condo with Heated Pool and Building Located on the Beach in LBK!br br The Beachcomber building and heated pool are located directly on the beach! Suite 501 has an island view of Longboat Key with a partial view of Sarasota Bay from the 5th floor. This condo does have a new full kitchen with maple cabinets and quartz counter top. Bedroom features a pillow top mattress for your comfort and also full bath. 50 inch HDTV in the living room with sofa, love seat and recliner for your enjoyment. The new sofa is a sleeper with premium mattress for additional guests. DVD player, HD cable, and Hi-Speed WIFI. Includes bath and beach towels, linens, beach chairs and most everything you need to enjoy your stay. Tennis, shopping, pharmacy, banking, and library are all within walking distance. Bike, kayak and boat rentals are available on Longboat Key. Also, we are minutes away from Siesta Key Beach and St. Armand's Circle with world class shopping and dining. Choose your level of sophistication. Come, relax and enjoy your stay.br br The Beachcomber is a well-maintained, six-story condo building located right on the beach, and has a lovely heated pool for the vacationers' exclusive use. Our friendly and helpful on-site managers will help ensure your vacation here is stress-free.br br What makes this condo unique br br Located on the Gulf of Mexico, the white sandy beach and pool are steps away from Suite 501. Only 10 steps to the elevators and 10 steps to the pool. The heated pool on the beach is great for sun worshipers and those looking for some natural vitamin D. There is an overhang that provides plenty of shade for any one that does not want too much sun or just relax under the palm trees. On a chilly day, there is a Sunset Room where you can relax inside and enjoy the sunset as you enjoy cocktails and conversations with new friends. You can grill on the beach while watching the sunset with plenty of tables for outside dining. After sunset, download an app and star gaze like you never have before when all the stars come out at night. Maybe there will be a turtle nest on the beach or you will see dolphins if you take a break from the book you have finally had a chance to finish. We once saw the space shuttle launch in the clear night sky from all the way over on the east coast. There is so much to do and so much to enjoy. Fall in love with Longboat Key while staying at the Beachcomber! Located on a barrier island, it is definitely is a unique tropical paradise.br br About the Owners: Philip and Angela br br We are from New England and appreciate getting away to warmer temperatures during the winter and planning a summer escape on the Cultural Coast of Florida or as we like to call our second home Longboat Key. We purchased this condo in 2002 after having a few disappointments while renting at other locations. We have enjoyed many vacations spent in Longboat Key and treasure the memories of our children having fun as they grew up. It is a great place for kids, a great place for families, and a great place for anyone whether you want to just relax or explore. To be honest, most families tell me that the pool is the best part for the kids. Long after their stay, the pool is what they are still talking about. Our family enjoyed all of our sunset swims while watching the sunsets night after night. There is also a grill available to cook on if you just want to stay at home and relax for an evening. Playing catch with a baseball, throwing a Frisbee, a quick game of touch football, flying kites, riding bikes, or just exploring has been great fun over the years. We hope you enjoy your stay as much as we do. Thank you.br br Why Philip and Angela chose Longboat Keybr br We have been traveling to Longboat Key for 25 years. We have known many friends that stayed on LBK also. After traveling to many islands, foreign countries, and cruises, we realized what a gem Longboat Key really is. The people that you meet in LBK are truly friendly. With so many things to do on the Key and surrounding areas, you can stay very busy or you can choose to just beach it. There is a sophisticated side to LBK also with the many restaurants and boutiques to visit. Or you can go fishing! Choose you own fun! Plan your adventure! Visit Longboat Key!br br Additional Info:br br Property Type:br br * Onsite Management. br * Guests provide their own meals.br * Housekeeping: Professional cleaners clean before you arrive and after your stay.br * Floor Area: 700 sq. ft. , 26 ft long deck.br * House Rules: Max. occupancy: 4, children welcome, pets not allowed, non smoking only.br br Location Type:br br * Resort, Beachfront, Partial Water View/Island View.br * Theme: Whatever you make it.br * Adventure, Romantic, Family, Away From It All, Historic places to see, Sports & Activities, br Tourist Attractions.br br General Info about the Condo:br br * FREE Internet WIFI.br * Plenty of Parking, Air Conditioning, and Heating.br * Linens Provided , Towels Provided, Beach Towels Provided.br * 4 Washing Machines and 4 Clothes Dryers located on the first floor next to the office.br * Hair Dryer, Iron & Board.br * 2 Elevators steps away.br br Kitchen: Dishes & Utensils, Pantry Items, Coffee Maker, Toaster, Dishwasher, Refrigerator, Stove with Oven, Microwave, br Dining Area: seating for 4 peoplebr Bathroom:br br * Bathroom 1 - toilet , combination tub/shower, tub. br * Full Bath with Rain Fall shower head. Sink with Pfister faucet. Plenty of spaces/cabinets to place your travel stuff! Bath towels are in linen closet. Professional cleaners do a great job providing you with a clean bath room (and entire condo) before to your arrival!br br Bedroom: br br * Features King Pillow Top Mattress, cable TV, full closet, and plenty of space to store your things during your stay. Also, new carpeting for comfort on your feet. br br Entertainment:br br Books, Toys near the beach, Television, DVD, Cable, Stereo br br Outside:br br * Beach, Pool, Swimming, Outdoor Grill, Lawn / Garden, Outdoor Gulf Front Patio, Bike Rack, Bike Pathbr br Things To Do/ Attractions nearby:br br * Tennis, Golf, Basketball Court, Shuffle Board, Recreation Center, Kayak / Canoe, Bicycles, Boating, Marina, Water Sports, botanical garden, arboretum, cinemas, library, museums, playground, theme parks, zoo, live theater, So Many Good Restaurants, churches, synagogues, health/beauty spa, and so many types of festivals. br br Leisure Activities:br br * Walking, eco tourism, outlet shopping, paddle boating, paddle boarding, sightseeing, beachcombing, bird watching, photography, miniature golf, antiquing, shelling, shopping, wildlife viewing, scenic drives br br Local Services & Businesses:br br * ATM/bank, Publix, CVS, bike/ kayak rentals, massage therapist, medical services, fitness centers, hospitalbr br Sports & Adventure Activities:br br * Parasailing, scuba diving or snorkeling, sailing, cycling, fishing, wind-surfing, roller blading, equestrian events, deep sea fishing, jet skiing, snorkeling.br br Notes:br br On site management with office hours during the day to help you with whatever questions or issues you may have. After hours number provided.br br On behalf of our guests and owners that suffer from asthma and allergies, no pets are allowed on the property. No exceptions! $300 fine.br Amenities Include:br - Balcony: Yesbr - Bed Size 1st/Master: Kingbr - Beds Pull-out: Queenbr - Ceiling Fans: bdrm/liv. rm/kit.br - Internet Access: Yesbr - Micro/Dishwash/Disp.: Yesbr - Refrig And Ice Maker: Yesbr - Square Footage, Est.: approx. 800 sq. feetbr - TV Cable/Satellite: Cablebr - TVs/VCR/DVD: 2/2/1br - View: Islandbr - washer dryer: on propertybr - Max number of People: 4br - Hair dryer: Yesbr - Bathtub/Shower: Yesbr - Beach front building: Yes

Beachcomber unit 501

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$476.88

Staying on Longboat Key means you get to experience what Heaven on Earth feels like. A place where you can walk on pristine white sands, bathe in the warm rays of the sun and take a bath in the clear waters of the Gulf.br br NEW KITCHEN RENOVATIONbr * New cabinets.br * Granite counters.br * Island and stools with gulf view.br * 2 bedroom; 2 bath second floor condo overlooking the Gulf of Mexicobr * 2 full baths with walk-in showersbr br * Sleeping accommodations: one king; two twinsbr * Free wireless internet. 3 TV's - One in living room and one in each bedroom.br * Gulf-side heated pool with lounge chairs and umbrella tablesbr * Private white sand beach, with terrific views from all roomsbr br br This Gulf front unit comes complete with a fully equipped kitchen, including all cookware, dishes and utensils, plus linens. br br Enjoy breathtaking sunsets from this second floor unit, with full Gulf views from the living room, dining room and both bedrooms. The living room and the master bedroom have brand new sliding doors that open onto a 34 foot long private balcony overlooking the beach and pool.br br Everything is here for your convenience, just bring your clothes and sunscreen!br br Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.br br The Beachcomber is a non-smoking bulding, including inside the unit and common areas. Smoking is permitted outside, including on the balcony.br br Please note: We do not allow Sunday or holiday arrivals and require a 7 night minimum stay.br Amenities Include:br - Balcony: Yesbr - Bed Size 1st/Master: Kingbr - Bed Size 2nd Rm: Twinsbr - Internet Access: Yesbr - Micro/Dishwash/Disp.: Yesbr - Refrig And Ice Maker: Yesbr - Square Footage, Est.: approx. 900 sq. feetbr - TV Cable/Satellite: Cablebr - TVs/VCR/DVD: 3 /0/1br - View: Gulfbr - washer dryer: on propertybr - Max number of People: 4br - Hair dryer: Yesbr - Shower only: Yesbr - Gulf view: Yesbr - Beach view: Yesbr - Beach front building: Yes

Beachcomber unit 202

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$1781.81

Escape to your own private island paradise! This spacious waterfront home sleeps up to 15 guests and offers the perfect mix of relaxation and fun.brbrbrFEATURESbrbr5 Bed, 5.5 BathbrPanoramic Water ViewsbrPrivate PoolbrPrivate BeachbrWater SportsbrFully stocked kitchenbrPrivate Pool and Hot TubbrExpansive Outdoor for Lounging & DiningbrbrAdventure awaits with complimentary kayaks, fishing off the dock, and endless water views from nearly every angle.brbrPRIME LOCATIONbrbrTucked away on Jewfish Key, this private island retreat is accessible only by boat. You’re just minutes by boat to Bradenton Beach Marina, Mar Vista, Shore, and other top waterfront restaurants.brbrWHY YOU'LL LOVE ITbrbr✔ Each bedroom features a private ensuite bathroombr✔ Private dock access for boats and jet skisbr✔ Surrounded by water views and island naturebr✔ Strong Starlink WiFi and Sonos sound systembr✔ Boat to nearby dining, shopping, and entertainmentbrbrROOM FOR EVERYONEbrbrFive (5) thoughtfully designed bedrooms, each offering comfort and privacy. Every bedroom includes its own ensuite bath for a relaxed, hotel-style experience.brbrCHEF-READY KITCHENbrbrFully stocked kitchen featuring stainless steel appliances, quartz countertops, and all the essentials — from cookware and dinnerware to a coffee maker for slow island mornings.brbrRELAX IN STYLEbrbrGather in the open-concept living and dining area, where comfort meets coastal design. Stream your favorite shows on the Smart TV, connect to Starlink WiFi, or play your favorite playlist through the Sonos sound system that fills the home with music.brbrBook your private island getaway today. brbrGUEST ACCESSbrThe property is accessible only by boat. Please note that you have to book your boat arrangements by yourself before going here.brbrRecommendation: Ben’s Boat Rentalbrhttps://bensboatrental.com/br• up to 10 personsbr• 2–3 days: $350/daybr• 4–7 days: $300/daybr• 8+ days: $275/daybr• Guests must refill fuel after usebr• Parking for up to 2 cars at 7018 Palm DrivebrbrDocking stations:brHome DockbrMost convenient spot with water and power hookups..brBe mindful of low tides.brbrIsland MarinabrLocated in the community marina, must use the designated outlined space.brIdeal for larger boats.brNo power or water connections.brbrPrivate Captain ServicesbrbrWhile we are not allowed in this app to share any links or contact numbers until your booking is confirmed, you can easily find them on Google if you’d like to check out their options.brbrOnce you've booked we can share with you our full guidebook with recommendations. brbrNOTE: 7018 Palm Drive is only available when renting through Ben’s Boat Rental and there isn’t designated parking for the home otherwise.brbrGETTING AROUNDbrThe island has no cars. It’s walkable via a dirt path connecting all homes. Flashlights help for evening walks.brbrThere’s a common dirt road running through the island. Great for exploring or getting around on foot.brbrFeel free to use available amenities such as paddleboards, outdoor seating, and the fire pit.brbrJEWFISH GUEST SERVICES: brMake your island stay effortless with optional boat transportation, grocery delivery, and fishing charters.brbrFishing Charters (up to 6 guests):brHalf Day Inshore: $600brFull Day: $1,200brbrGrocery Boat Delivery:brPublix (Anna Maria Island only)brGuests place order; we deliver to the home (not unpacked)br$325 per deliverybrbrBoat Transportation:brDock transfers (1-hour notice): $65 per tripbrLast-minute transfers (under 1 hour): $95 per tripbrGuest & luggage transport (up to 2 hours): $400brbrBoat Service:brHalf Day: $450brFull Day (8 hrs, unlimited nearby trips): $900br brPlease contact Captain Ryan Killoran to schedule your fishing charter.brbrFor all other services please contact Tyler Hershberger. brbrNEARBY DININGbr(Note: There is no food options on the island.)brbr• Shore – 5 mins.br• Mar Vista – 5 mins.br• Whitney’s – dock at Palm Dr., 5-minute walkbr• Starfish Market – 10 minutes (cash only, great for fresh seafood)br• Tide Tables and Seafood Shack – nearby favoritesbr• Bridge Street – public boat parking, restaurants, shops & mini-golfbr• Marina Jack’s – 15–20 mins. to downtown SarasotabrbrWHAT TO BRINGbrswim shoes, waterproof bag, extra lifejackets, flashlights, binoculars, sunscreen, bug spray, and basic paper goods.brbrRRCR#- RRR-00784.2025

Private Island Oasis

Longboat Key, Florida, United States

5

Bed

5

Bath

15

Sleeps

$3009.49

Welcome aboard! The Ship House is one-of-a-kind 2,400 sq. ft. waterfront retreat on Jewfish Key, a private 38-acre island near Longboat Key. Fully renovated in 2025 to resemble an 18th-century sailing ship. This unique home offers luxury, comfort & privacy for an unforgettable island getaway.brbr- Sleeps up to 13 guests with 4 themed bedrooms & 3.5 bathsbr- Private Captain’s Quarters with ensuite bathbr- Expansive decks and water views from every anglebr- Fully equipped kitchen and modern amenitiesbrThe spacebrPRIME LOCATIONbrbrTucked away on Jewfish Key, this private island retreat is accessible only by boat. You’re just minutes by boat to Bradenton Beach Marina, Mar Vista, Shore, and other top waterfront restaurants.brbrWHAT YOU'LL LOVEbrbr✔ 4 bedrooms, 3.5 bathrooms and 2 additional twin beds to sleep a total of 13br✔ Open loft-style layout with tons of natural lightbr✔ Outdoor tub with hot and cold waterbr✔ Spacious deck and outdoor seating areasbr✔ Perfect for family vacations, friend trips, and group getawaysbrbr✔ Private dock access for boats and jet skisbr✔ Private island location surrounded by water viewsbr✔ Strong Starlink WiFi and Sonos sound systembr✔ Boat to nearby dining, shopping, and entertainmentbrbrOPEN LOFT LIVINGbrThis spacious 4-bedroom, 3.5-bathroom island home is the perfect place to relax, recharge, and make lasting memories with family and friends. Inside, you’ll find bright, airy spaces with high ceilings and an open loft layout that brings everyone together.brbrPRIVATE LOCATIONbrLocated on a private island surrounded by calm waters, this home combines laid-back coastal living with a unique open design.brbrLARGE KITCHENbrThe large kitchen is perfect for cooking group meals, while the living area makes for a great spot to unwind after a day on the water.brbrWATER VIEWSbrStep outside and take in the views from every angle. Enjoy morning coffee on the deck, watch the sunset over the water, or gather for a barbecue under the stars. Whether you’re kayaking, lounging, or just soaking up the island vibes, this home has everything you need for a fun and easygoing getaway.brbrBook your private island getaway today. brbrGUEST ACCESSbrThe property is accessible only by boat. Please note that you have to book your boat arrangements by yourself before going here.brbrRecommendation: Ben’s Boat Rental brhttps://bensboatrental.com/br• up to 10 personsbr• 2–3 days: $350/daybr• 4–7 days: $300/daybr• 8+ days: $275/daybr• Guests must refill fuel after usebr• Parking for up to 2 cars at 7018 Palm DrivebrbrDocking stationsbrFront Dock – Best for smaller boats (includes 2 jet ski lifts).brRear Dock – For larger boats, with designated docking spots.brbrWhile we are not allowed in this app to share any links or contact numbers until your booking is confirmed, you can easily find them on Google if you’d like to check out their options.brbrOnce you've booked we can share with you our full guidebook with recommendations.brbrNOTE: 7018 Palm Drive is only available when renting through Ben’s Boat Rental and there isn’t designated parking for the home otherwise.brbrGETTING AROUNDbrThe island has no cars. It’s walkable via a dirt path connecting all homes. Flashlights help for evening walks.brbrThere’s a common dirt road running through the island. Great for exploring or getting around on foot.brbrFeel free to use available amenities such as paddleboards, outdoor seating, and the fire pit.brbrJEWFISH GUEST SERVICES: brMake your island stay effortless with optional boat transportation, grocery delivery, and fishing charters.brbrFishing Charters (up to 6 guests):brbrHalf Day Inshore: $600brFull Day: $1,200brGrocery Boat Delivery:brbrPublix (Anna Maria Island only)brGuests place order; we deliver to the home (not unpacked)br$325 per deliverybrBoat Transportation:brbrDock transfers (1-hour notice): $65 per tripbrLast-minute transfers (under 1 hour): $95 per tripbrGuest & luggage transport (up to 2 hours): $400brBoat Service:brbrHalf Day: $450brFull Day (8 hrs, unlimited nearby trips): $900br brPlease contact Captain Ryan Killoran to schedule your fishing charter.brbrFor all other services please contact Tyler Hershberger. brbrNEARBY DININGbr(Note: There is no food options in the island.)brbr• Shore – 5 mins.br• Mar Vista – 5 mins.br• Whitney’s – dock at Palm Dr., 5-minute walkbr• Starfish Market – 10 minutes (cash only, great for fresh seafood)br• Tide Tables and Seafood Shack – nearby favoritesbr• Bridge Street – public boat parking, restaurants, shops & mini-golfbr• Marina Jack’s – 15–20 mins. to downtown SarasotabrbrWHAT TO BRINGbrswim shoes, waterproof bag, extra lifejackets, flashlights, binoculars, sunscreen, bug spray, and basic paper goods.

The Ship House

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$366.96

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrLimited Membership Privileges: Guests of Silver Sands Gulf Beach Resort #242 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #242 Features: 1-bedroom, 1-bathroom unit in the Green Building with a direct pool view and a distant Gulf view from your private lanai.brbrbrbrView: Pool/Gulf ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Poolside Peace – Silver Sands Resort #242 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$331.35

Beach Castle Resort #24 – Bayside Bliss on Longboat Key - A Romantic, Waterfront Retreat by RVA Resort VacationsbrbrbrbrEscape to paradise at Beach Castle Resort #24, a bayside gem on the exclusive island of Longboat Key, Florida. Perfectly positioned between Sarasota Bay and the Gulf of Mexico, this one-bedroom, one-bathroom vacation condo delivers the best of both worlds—breathtaking bay views and private beach access just steps away.brbrbrbrYour Longboat Key Coastal Escape - Wake up to stunning views of the bay, sip your morning coffee on your private lanai, and feel the ocean breeze drift through this serene island hideaway. Unit #24 has been beautifully updated with new furnishings, a king-sized bed, and modern appliances to enhance your comfort. The bright, beach-inspired décor captures the essence of coastal living, creating a peaceful atmosphere for relaxation and romance.brbrbrbrEnjoy thoughtful touches including:br-Spacious open living area with full-size sleeper sofabr-Fully equipped kitchen with new appliances and dining spacebr-Smart TVs, high-speed Wi-Fi, and keyless entry for effortless conveniencebr-Private lanai with panoramic bay views – perfect for sunsets or quiet reflectionbrbrbrbrResort Amenities That Redefine Relaxation...brbrGuests of Beach Castle Resort enjoy exclusive resort-style amenities designed for relaxation and recreation:br-Private beach access with complimentary lounge chairs and umbrellasbr-Heated community pool and hot tub surrounded by lush tropical landscapingbr-Shared boat docks (first-come, 26’ boat limit) for water adventuresbr-Outdoor grills, on-site office, and complimentary laundry facilitiesbr-Assigned parking and guest parking availablebrbrbrAs an added bonus, guests of Unit #24 receive limited membership privileges at Cedars Tennis Resort, offering access to:br-Har-Tru tennis and pickleball courts (after 1 p.m., subject to availability)br-Community bicycles, fishing pier, fitness center, and a Jr. Olympic heated poolbrbrbrBeach Castle Resort is a hidden treasure on Longboat Key—a quiet, 21-unit property known for its lush tropical grounds, charming Bahama-style architecture, and unbeatable location. Whether you’re kayaking on the bay, fishing from the dock, or watching the sunset over the Gulf, this is where vacation memories are made.brbrbrbrFrom romantic getaways to small family escapes, Unit #24 delivers all the ingredients for a perfect stay: tranquility, style, and proximity to the very best of Sarasota and Longboat Key.brbrbrbrView: Bay ViewbrbrbrbrBedding: 1 King Bed + Full-Size Sleeper SofabrbrbrbrOccupancy: Up to 4 guestsbrbrbrbrParking: On-SItebrbrbrbrPets: Not permittedbrbrbrbrHousekeeping: Self-service resort; a starter kit is provided at check-inbrbrbrbrExperience the perfect blend of bayfront serenity, Gulf-coast adventure, and resort-style comfort at Beach Castle Resort #24. Whether you’re planning a romantic retreat or a relaxing family escape, this Longboat Key vacation rental invites you to unwind, explore, and reconnect with what matters most.brbrbrbrReserve your stay today at Beach Castle Resort #24 – your waterfront paradise awaits!

Seaside Escape – Beach Castle #24 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$334.62

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrLimited Membership Privileges: Guests of Silver Sands Gulf Beach Resort #258 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #258 Features: 1-bedroom, 1-bathroom unit in the Orange Building. Includes views of both the pool and Gulf of Mexico from your private patio. Unit has recently received a luxury pillow top mattress topper for those that prefer a softer rest.brbrbrbrView: Pool/Gulf ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$324.18

Our building is located on the beach, this unit has an ISLAND view.br br Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.br br Please note: We do not allow Sunday or holiday arrivals and require a 7 night minimum stay.br br 1 bedroom, 1 bath, fourth floor condo overlooking the Island towards Sarasota Baybr br * King size bedbr br * Queen sleeper sofa in living roombr * Free wireless internet accessbr * Gulf side heated pool with lounge chairs and umbrella tablesbr * Covered beachside seating areabr * Private white sand beachbr br This island-side unit is completely furnished and sleeps a maximum of 4 people. The unit was refurbished in 2016. All bed linens, dishes, cooking and eating utensils are provided. The kitchen has all stainless-steel appliances. There are flat screen TVs in the living area and the bedroom with free cable. br br Off the living room is a spacious private balcony where you can watch the sunrise over the island while enjoying morning coffee.br br It's all here, just step out of the building and you're on the beach!br br On behalf of our guests and owners that suffer from asthma and allergies, no pets are allowed on the property. No exceptions! $300 fine.br Amenities Include:br - Balcony: Yesbr - Bed Size 1st/Master: Kingbr - Beds Pull-out: Queenbr - Ceiling Fans: kitchenbr - Internet Access: Yesbr - Micro/Dishwash/Disp.: Yesbr - Refrig And Ice Maker: Yes/Nobr - Square Footage, Est.: approx. 800 sq. feetbr - TV Cable/Satellite: Cablebr - TVs/VCR/DVD: 2/0/0br - View: Islandbr - washer dryer: on propertybr - Max number of People: 4br - Hair dryer: Yesbr - Bathtub/Shower: Yesbr - Beach front building: Yes

Beachcomber unit 403

Longboat Key, Florida, United States

Bed

Bath