Vacation Home Rentals By Owner In Longboat Key, FL

Welcome to Longboat Key - paradise awaits! Large newly renovated, spacious and bright 2 bed/2.5 bath 3 story townhome with picturesque sunset views and privacy. Located in the Cedars East Tennis Resort Community, complete with a heated Olympic sized pool. Renters have access to clay tennis courts, pickle ball courts, fitness center and enjoy free WIFI in unit. Short walk to Longboat Key's famous white sand beaches, Harry's Restaurant, Joan Durante Nature Trail, Lazy Lobster and Blue Dolphin Breakfast Place. Short drive to world famous shopping and restaurants in St. Armand's Circle as well as world famous IMG Academy.

Cedars East Townhome on beautiful Longboat Key

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$319.84

Welcome to The Tree House in Cedars East Longboat Key!br⚓Short bike ride to beaches br⚓Community Pool, Kayak Launch, Nature Trails, Fishing & Morebr⚓Less than 1 mile to Joan Community Parkbr⚓Fully stocked kitchen for all of your favorite home cooked meals br⚓High speed Wi-Fi included Smart lock for Self-Check-in brbr2 Bedroom Townhome Sleeps 6brWelcome to the Tree House! This recently renovated, and freshly furnished property is located in the beautiful community of Cedars East Tennis Resort. The Tree House is nestled between protected mangroves and the Sarasota Bay. It is located on the North end of Longboat Key and offers the perfect location for your vacation getaway, being close to restaurants, shopping, and of course the beach! Situated on a private cul-de-sac with views of the Sarasota Bay, this unit is just steps away from a kayak/stand-up paddleboard launch, which is also an amazing spot for shelling during low tide. A private fishing doc is located in the cul-de-sac as well, complete with picnic table and umbrella. brbrThe Tree House is located in the secluded back section of the community. Upon entering, you instantly notice the high-end finishes, thoughtful details, and quality furnishings, making this property truly a home away from home! The living room features a large flat screen, smart tv and a high-quality sound system. High-speed internet is available throughout the house. The kitchen is fully equipped with everything a chef requires and even offers a few added bonuses we are sure you will enjoy! For all you grill lovers, there is a propane grill for cooking up your catch of the day! The centerpiece of the home is the walnut river dining table, specifically designed for the space and made by the owner. brbrBoth bedrooms are located on the top level. The master bedroom offers a king-size bed, flat-screen tv, reading chair, and desk-making it the perfect work-from-home space. The master bathroom, separated by barn doors, offers double vanity sinks and a walk-in shower. The second bedroom offers a queen-size bed, flat-screen tv, and a hall bathroom. Additional sleeping options are located downstairs with both living room furniture pieces converting to sleeper sofas (queen and single). The unit offers beach essentials such as 6 beach chairs, a beach umbrella, as well as 4 bikes for exploring the island! When relaxing on the lanai or working at the desk in the master bedroom, you feel as if you are in a tropical treehouse. You can even watch the ospreys soar by at eye level as they head to the bay for their next meal. brbrMaster Bedroom - King Bed, Ensuite Bathroom, TV, DeskbrBedroom 2 - Queen Bed, TVbrLiving Room - Sleeper SofabrbrWith all rentals, you have access to the community pool, kayak launch, nature trails, and fishing pier. For an additional fee, you can gain access to the tennis resort and fitness center as well! brbrFill your next vacation with relaxation and seaside fun when you book your trip to this stunning Florida property!brbr*Dogs under 20lbs allowed with a $100 fee per pet with prior approval. Number of pets limited based on owner preference. No aggressive breeds allowed per insurance. Inquire for more info. br*Non-smokers pleasebrbrDamage Waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee (“Management”), plus tax if applicable (the “Damage Waiver”).brThe Damage Waiver covers you for up to $1,500 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the “Rental Agreement” on the checkout page.

⚓The Tree House! Beautiful townhome in Longboat Key with great amenities surrounded by nature!⚓

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$1837.96

Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience for you and your family like no other. brbrThe house has 4 bedrooms and 4 bathrooms and an outdoor shower. All rooms view out over the azure waters of Longboat Pass, with 300 feet of beachfront, palm trees, shaded hammocks, and private dock. brbrBoat Access - Reasonably priced discounted local boat rentals are available for our guests from Cannons Marina on Longboat Key or Bradenton Beach Marina - both a short distance away from the Island in protected well marked Inter-coastal waters. Or bring your own boat.brbrHouse - The house opens on both the east and west side with 4 pocketing 12 foot sliding doors opening onto large screened decks for lounging and dining. brbrSleeping - The main floor Master bedroom deck has an outdoor claw-foot tub with hot and cold water and private bath with large shower. One of the upstairs 2-room bedroom suites sleeps up to 5, and the other sleeps 3. Both have private baths. All bedrooms open onto decks overlooking the azure color of our water and daily sunsets. Bed totals = 4 queen custom made beds with one capable of being separated for two twins + 4 X-long twins. All Linens and towels are provided.brbrKitchen - Fully equipped kitchen with Sub-Zero, Wolf and Kitchen Aid Appliances, as well as a Kitchen Aid food processor and Vita-mix blender, coffee maker, Kureg Pod Machine. Sonos Sound system with wireless streaming and High Speed Wifi. Surrounded by fine-dining, one of the prettiest beaches and amazing fishing, there is plenty to keep you busy – or swing in the hammocks and order Pizza to be delivered to the town dock.brbrThe house faces west for spectacular sunsets. You are surrounded by pristine boating and swimming water the best gulf and bay fishing on the west coast of Florida. You will have use of 2 stand up paddle boards, 2 double person kayaks, 2 children's kayaks and a canoe. We also have a variety of fishing poles but for serious fisherman you should bring your own salt water fly or cast rods. Surrounded by Wildlife. During a typical stay you will see dolphins playing off the beach, manatees often, tarpon, sea turtles and a large array of gulf coast fish. For bird lovers you will see and hear osprey, great horned owls, pileated woodpeckers, great blue herons, egrets, wood storks, roseate spoonbills, screech owls, white and brown pelicans, frigates, cormorants, anhingas and many other sea birds. There are no poisonous snakes or other dangerous wildlife on island....brbrFishing. Fly and cast fishing is epic as the waters surrounding the island are nick-names by the locals as The Kitchen - and are teeming with gulf-coast fish.brbrBeach-combing is also wonderful on property and on the large sandbar to our north. Exploring our private island is fun for all. The kids will enjoy the 200' Zip line.brbrThere is High speed internet with Apple TV, Smart TV and Sonos with access to Netflix, Amazon and other movie options. Residential Rental Cert. RRR-00843.2023

Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets

Longboat Key, Florida, United States

Bed

Bath

10

Sleeps

$290.92

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public, it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #852 Accommodations: 2-bedroom, 2.5 bathroom townhome with garden views in the private Preserves location of Cedars community.brbrbrbrUnit Amenities: Wireless Internet, 1-Car Garage, Full-size Kitchen, Private Lanai, Fitness Facility, Community Pool, Beach Access (A Short Distance Away).brbrbrbrLocation: 852 Evergreen WaybrbrbrbrView: Garden ViewbrbrbrbrBedding: 2 KingsbrbrbrbrMinimum Night Requirements: Minimum Stays Apply

Play all Day Cedars #852 Pet-Friendly by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$581.38

Newly renovated, this beautiful home features a split floor plan with generously sized bedrooms and walk-in closets, all enhanced by a charming coastal flair. The kitchen—truly the heart of the home—is fully equipped with everything you need to prepare delicious home-cooked meals. Enjoy your morning coffee or an evening cocktail in the cozy coffee-bar area.brbrStep outside to the brand-new pool and spa. One end offers a shallow sun-shelf perfect for soaking or sunbathing before you slip into the refreshing deep end. The expansive stone pool deck provides plenty of space to relax on the lounge chairs and soak up the Florida sunshine.brbrWelcome to peaceful Buttonwood Harbour, a community of just 50 homes located in one of Longboat Key’s most established and desirable neighborhoods. Perfectly situated in the center of the island, you’ll be within walking distance to Publix, the Shoppes of Bay Isles, tennis courts, the post office, and CVS. The neighborhood is known for its friendly atmosphere and natural beauty, making it a favorite for outdoor enthusiasts.brbrBoaters and fishermen will appreciate access to the BHA boat ramp, the ability to dock a boat at the home during your stay, and available kayak storage if you choose to rent them. With no bridges between Buttonwood Harbour and the open waters of Sarasota Bay, getting out on the water is easy. Bayfront Park is just 1.4 miles away and offers a 1,350-square-foot indoor recreation center, playground, basketball court, shuffleboard, multipurpose open field, three dedicated pickleball courts, a tennis court, picnic areas, restrooms, and convenient parking for the public beach access across the street. There`s also a dog park for your furry companions.brThere must be a minimum of (2) adults overbrthe age of 30 as named tenants. We do not lease to young adults without adults over the age of 30 on the premises.brbrRefundable damage deposit of $2000

Longboat Key Waterfront: Private Heated Pool w/ Soaking End & Luxury Hot Tub!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$314.49

Escape to Paradise at Cedars East Tennis Resort – Longboat Key Luxury Townhome by RVA Resort VacationsbrbrbrbrWelcome to Cedars East Tennis Resort, your exclusive Longboat Key vacation destination by RVA Resort Vacations. Nestled along Florida’s stunning Gulf Coast, this luxury townhome resort offers the perfect balance of relaxation, recreation, and refined comfort. Whether you’re here for a romantic getaway, a family vacation, or a tennis-filled retreat, Cedars East invites you to experience the best of coastal living on Longboat Key.brbrbrbrStep inside your spacious, fully furnished vacation townhome, thoughtfully designed for both style and comfort. Each residence features bright, open living spaces with coastal-inspired décor, a full-size kitchen with breakfast bar, a separate dining area, and—available in select units—a private screened lanai for morning coffee or evening sunsets.brbrbrbrEvery detail has been curated to make your stay effortless, from modern appliances and wireless internet to plush bedding and private parking. Discover your Longboat Key getaway at Cedars East Tennis Resort Unit #804, a luxurious 2-bedroom, 2.5-bathroom townhome tucked away in the exclusive Preserves area. Enjoy the perfect mix of Gulf Coast serenity, modern comfort, and resort-style amenities—designed for both relaxation and recreation.brbrbrbrBedroom Details:brRelax in comfort with thoughtfully designed sleeping arrangements ideal for families or couples. Master Bedroom: Features a plush King bed with premium linens, offering the perfect retreat after a day of sun and island adventure. Second Bedroom: Includes two comfortable Twin beds, ideal for children or additional guests.brbrEach bedroom is tastefully furnished with coastal décor and ample storage, creating a serene and restful atmosphere during your Longboat Key getaway.brbrbrbrResort Amenities That Redefine Relaxation - At Cedars East Tennis Resort, every day feels like a vacation. Enjoy access to a full suite of resort amenities designed to inspire activity, leisure, and connection.brbrbrbrTennis and Pickleball Courts – Play on 10 Har-Tru (soft-clay) courts, with access to professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts are also available.brbrbrbrPro-Shop – On-site shop offering tennis and pickleball gear, apparel, and help with court reservations.brbrbrbrJunior Olympic-Sized Heated Pool – Relax or swim laps in the resort’s expansive heated pool, complete with complimentary chaise lounges and a seasonal Tiki Bar.brbrbrbrFitness Center – Work out anytime in the modern 24-hour fitness facility with secure access.brbrbrbrBicycles for Guests – Complimentary adult-sized bikes are available for exploring the scenic Gulf of Mexico Drive and nearby attractions.brbrbrbrHugo II Restaurant – A seasonal European Fusion dining experience featuring German, Czech, and Italian-inspired dishes with specialty Prosecco cocktails. Private dining memberships are included for Cedars Club guests.brbrbrClubhouse and Social Spaces – Enjoy social gatherings in the Clubroom and bar area, or relax in cozy communal lounges.brbrbrbrFishing Pier and Mangrove Boardwalks – Stroll along charming boardwalks through the mangroves leading to a serene fishing pier, ideal for picnics, watching marine life, or taking in sunset views.brbrbrbrBeach Access and Island Adventures - The Gulf of Mexico shoreline stretches endlessly along Longboat Key, offering soft sand and sparkling turquoise waters. Guests of Cedars East are welcome to enjoy the beach via designated Public Beach Access points clearly marked along Gulf of Mexico Drive.brbrFor even more adventure, take a short drive to St. Armands Circle and downtown Sarasota for fine dining, boutique shopping, art galleries, and live entertainment.brbrbrbrAmenities: Wireless Internet, Full-Size Kitchen, Private Lanai, 1-Car GaragebrbrbrbrLocation: 804 Evergreen Way, Longboat Key, FL 34228brbrbrbrView: Garden and Partial Bay ViewsbrbrbrbrWhether you’re here for the world-class tennis, resort amenities, or simply the peaceful coastal ambiance, Cedars East Tennis Resort by RVA Resort Vacations offers everything you need for a luxury Gulf Coast escape.brbrbrbrBook your stay today and discover why Cedars East remains one of the most sought-after Longboat Key vacation resorts on Florida’s Gulf Coast.brbrbrbrMinimum stay requirements apply

Tennis & Beach Retreat – Cedars East #804 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$819.92

Highlightsbr• Half-mile walk or bike ride to Whitney Beachbr• 3 Bedroom, 2 Bathroombr• Balcony overlooking tranquil Bishop Bay/Canalbr• 1 King, 1 Queen, 1 Queen br• Private poolbr• Screened lanai off kitchen overlooking the poolbr• BBQ Grillbr• In-unit washer and dryerbr• Free parking br• Beach chairs and a cart includedbr• Close to popular dining options and local shopsbrbrLBK Whitney Bayside by Reel Coastal Propertiesbr625 Jackson WaybrLongboat Key, FL 34228brbrWelcome to LBK Whitney Bayside, a stunning luxury retreat on Longboat Key. Tucked away on a quiet street just a half mile from the beach, this elegant 3-bedroom, 3-bathroom home combines modern sophistication with the relaxed charm of coastal living.brbrStep inside and you’ll find soaring ceilings, high-end finishes, and a designer kitchen fully equipped for the chef at heart. The open living space flows seamlessly to the outdoor patio, where you can relax with a glass of wine overlooking the tranquil canal or take a dip in the heated pool.brbrEach bedroom is designed with comfort in mind, offering privacy and style:br • Master Bedroom – King bed, flat-screen TV, ensuite bathroombr • Guest Bedroom 1 – Queen bed, flat-screen TV, ensuite bathroombr • Guest Bedroom 2 – Queen bed, flat-screen TV, ensuite bathroombrbrWhether you’re preparing a meal in the gourmet kitchen, lounging poolside, or heading out to explore the pristine white-sand beaches of Longboat Key, this home is the perfect place to unwind.brAdditional amenities include Wi-Fi, washer/dryer, outdoor seating, and easy access to local dining, shopping, and activities. With its serene setting and luxurious details, this home offers an unforgettable island getaway.brbrRoom Detailsbr- Master Bedroom: King bed, tv, and ensuite bathroombr- Guest Bedroom 1: Queen bed, tv, and ensuite bathroombr- Guest Bedroom 2: Queen bed, tv, and ensuite bathroombrbrThere are no pets allowed in this home.brbrPlease Remember:brYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrRules:br • No dog(s) are permitted in this home. No other animals are allowed without specific ReelCoastalProperties approval.br • No Parties/Unauthorized Events and absolutely No Smoking or VapingbrbrLBK Rental Permit: RRR-01431.2025 (30-day minimum rental period)

LBK Whitney Bayside Retreat

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$353.53

Beautiful 2 story private townhome has been recently updated in a bohemian beach vibe with warm pinks, blues and greens that match the longboat key water. This home is graciously spread over three levels. On the ground floor is a two car tandem garage with extra storage space for beach toys. The first floor welcomes you with a large sectional sofa facing the 55 smart TV and veranda facing the mangroves. A bright newly renovated generous kitchen is equipped with everything that is needed to enjoy your stay. Spread out with enough kitchen equipment to cook a great meal or cook on the gas grill located in the garage. A half bath is also located on the main floor. Head upstairs where you will find the master bedroom with large walk-in closet, desk with keyboard, mouse and monitor including laptop hookup.The master bath has dual vanities both with their own mirrors that connects to the shower and bath combo. Exit the master bedroom walk down the hallway and find the guest bathroom with a spacious stand-up shower. Go further down the hall and you will find the guest bedroom with a full over full bunkbed with a pull out trundle. Additionally there is a stacked washer and dryer in the guest bedroom. Back to the garage there are plenty of beach toys to take to the beach and you are just steps from the junior olympic size swimming pool. Amenities of the community include restaurant and tiki bar. You are also a short walk/ quick bike ride from a coffee shop, convenient store, Mexican restaurant and the world famous Harry Restaurant and store. Tennis club with new pickle courts and gym may be available for an extra fee. Please contact for further details. Enjoy the crystal clear waters of longboat key! Unfortunately there is not direct beach access. Please reach out with questions.

Private townhome steps from the beach and right next to the pool

Longboat Key, Florida, United States

Bed

Bath

9

Sleeps

$358.94

Discover the magic of Longboat Key! Relax and refresh at this spacious and Beautiful, newly renovated, unique and tranquil getaway in the Best location on Longboat! A short two block walk to the best beach in Sarasota and walk to the best restaurants (The shore, Mar Vista, Whitney’s, to name a few) Enjoy fishing, walking the moonlight alleyways and delight in daily visits/feeding our Pet Peacocks right from your yard. A truly delightful a memorable experience! Private neighborhood boat ramp if needed. You will be completely surrounded by water in tropical beach paradise known for the best sunsets anywhere! The Best Beach is a short 2 block walk. The Large Backyard is a true tropical paradise including shaded lounging, outdoor dining, sunbathing, cornhole and a firepit. This property also comes with a large 1/1 separate detached guest house with Kitchenette, providing complete privacy and additional space. This is a new listing so no reviews yet but I promise you will be very pleased :)

Longboat Key Modern Beach House Gem

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$661.11

brNewly renovated Sarasota Bay front house with unobstructed view. Large two-story villa has everything you need for your island getaway. House is comfortably furnished and well maintained. Each of the bedrooms and the living area has its own flat screen TV. WiFi internet access also included. Pool heat is optional at additional $140/week.brEnjoy your oversized private pool with large patio and grill. You can fish or just relax on the bay dock or walk across the street to white sand Gulf beaches with our own beach chairs. Within walking distance to the Centre Shops dining and shopping. Nearby St. Armand's Circle boasts the finest in restaurants, wonderful shops and relaxing scenes. Downtown Sarasota thrives with cultural activities such as theatres, jazz clubs and wonderful antique stores. brbrThe area is a golfer's paradise with world class golf courses within a short drive! For family fun, the Busch Gardens theme park is just an hour away in Tampa, and Disney World in Orlando is just a two and a half hour drive away. br Saturday Check In/Check-Out is preferred. Welcome to paradise!brbrKeywords: House

Bayfront Longboat Key House with Pool and 3 min walk to the beach

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$884.08

Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis / Pickle Ball court. For the boater enthusiasts, enjoy docking your boat/yacht in your private, deep-water dock.brbrThis 4000 square foot home is perfect for entertaining and accommodating all your friends and family. This home offers four large bedrooms and three-and-a-half bathrooms. Located on the main floor are three bedrooms; one of which includes an en-suite bathroom. The over-sized Master suite, which is located on the top floor, features his and hers walk-in closets, en-suite bathroom with jetted tub, large walk-in shower with multiple spray heads, his and her sinks and vanities and private toilet with bidet. The Master bedroom also features an en-suite sitting/reading area with beautiful Bay and Inter-coastal panoramic views.brbrThe formal dinning room features an eight person dinning table with unobstructed Bay and Inter-coastal views. The fully stocked, large Chef kitchen, built for entertaining, comes with: a six burner Viking gas stove, flat top grill, two ovens and pot filling faucet. This eat in kitchen also features granite counter tops throughout, with two dishwashers, large Viking freezer/refrigerator ice maker with a second under the counter refrigerator, and a four seat marble top table. This kitchen also has a dual side wood-burning fireplace with a flat screen TV on top of the mantel. brbrThe spacious living room offers unobstructed Bay and Inter-coastal views. This room is beautifully decorated and it also features a wood-burning fireplace for those chilly nights with a wall mounted flat screen TV. The living room, as well as the eat-in kitchen, have disappearing sliding doors which lead to the enclosed, outdoor patio and private pool. brbr** Note**brGuest are provided with minimum one day supply of start-up items;brpaper towel, hand soap, toilet paper & garbage bags, et.

Hidden Bay/Beach Paradise

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$300.11

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public, it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #847 Accommodations: 2-bedroom, 2.5 bathroom townhome with garden views in the private Preserves location of Cedars community.brbrbrbrUnit Amenities: Wireless Internet, 1-Car Garage, Full-size Kitchen, Private Lanai, Fitness Facility, Community Pool, Beach Access (A Short Distance Away)brbrbrbrLocation: 847 Evergreen WaybrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, 1 Queens, Sleeper sofabrbrbrMinimum Night Requirements: Minimum Stays Applybrbr**The condo is currently for sale and will be subject to showings with advance notice.

Pet-Friendly Cedars East Unit 847 by RVA

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$351.1

You will pinch yourself that you are staying on such a gorgeous island in a beautiful townhome! Every morning you will look out your windows and see the painted colors of the sunrise on the Bay. Every evening you can watch the majestic colors of the sunset on the Gulf, which is within walking distance across the street. Take a walk on the beach barefoot with the white, powdery sand in your toes. Go for a swim in the heated clubhouse junior olympic size pool, play tennis or pickle-ball, and take a bike ride! Explore St. Armands, AMI, Lido & Siesta Key! Enjoy!

Gorgeous townhouse in desirable Cedar's East Tennis Resort!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$355.34

Welcome to Bay Haven Home by RVA in the popular community of Country Club Shores. A large master bedroom suite, two guest bedrooms with multiple sleeping options, and a large living area this home is perfect for traveling families, groups or couples. The open-air pool opens to the community canal that includes amazing water views. Take a dip in your private pool while soaking in the warm Florida breezes and enjoying the sunshine. Bay Haven Home has all the elements needed for a relaxing vacation. brbrbrbrAmenities include wireless Internet access, garage parking and pets are allowed (with prior approval) so bring the entire family for an island getaway.brbrbrbrAccommodations: Three-bedroom, two-bathbrbrbrbrAmenities: Great Views, Spacious Floor Plan, Nicely Decorated, Private Boat Dock, Large Patio, Private Pool, Full-size Kitchen, Grill, Washer/Dryer, Pets Allowed, Wireless Internet AccessbrbrbrbrLocation: 530 Bowsprit Lane, Longboat KeybrbrbrbrBedding: 1 King, 1 Queen, 2 TwinsbrbrbrbrView: Water ViewbrbrbrbrMinimum Night Requirements: Restrictions ApplybrbrbrbrPet Policy: An additional pet fee will be added to applicable bookings, and cannot be processed online. To reserve a pet-friendly booking contact our local team. Pets not given prior approval will not be accepted.brbrbrbrOther: Additional electric and/or pool heat charges may apply; please call our local offices for details.brbrA security camera is mounted on the exterior of the property, pointing towards the dock, to monitor the owner's boat.

Bay Haven Home on Longboat Key by RVA

Longboat Key, Florida, United States

3

Bed

Bath

6

Sleeps

$306.73

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public, it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #830 Accommodations: 2-bedroom, 2.5 bathroom town home with bay views from your private patio.brbrbrbrUnit Amenities: Nicely Decorated, Flat Screen TVs, Wireless Internet, Full-size Kitchen, Private Lanai, Fitness Facility, Community Pool, Beach Access (A Short Distance Away)brbrbrbrLocation: 830 Evergreen Place, Longboat KeybrbrbrbrView: Bay ViewbrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrMinimum Night Requirements: Minimum Stays Apply

Bay Breezes 2BR / Pet-Friendly Cedars East RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$338.91

This home requires a 28-night minimum stay.brbrArts and Vines by Anna Maria Life Vacation Rentalsbr6836 Pine St, Longboat Key, FL 34228brbrWhat You'll Love About This Home:brLocation! Beautiful Longboat Key!br3 Bedrooms / 2.5 BathroomsbrKing, Queen, 2 Twins, Full Sofa BedbrPrivate Heated Pool & SpabrPool LoungersbrCovered Poolside Lounge with Patio DiningbrRooftop Deck with Lounge SeatingbrGas GrillbrOutdoor Balcony DiningbrMultiple Decks Overlooking Lush Backyard & PoolbrFenced YardbrDog Friendly - with fee. See below. Max 2 small dogs.brProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach TowelsbrParking for 5 CarsbrbrDetails:brLocated on Longboat Key's barrier island, with gorgeous, peaceful, quiet beaches offering soft white sand, turquoise water, and dramatic sunsets, Arts & Vines radiates a vibrant, artistic vibe showcasing bright, beach themed artwork throughout. Our art-filled retreat is welcoming and full of character. Step inside and feel like you are walking through a beachside gallery full of color and personality.brbrThe main level features a beautifully integrated kitchen, dining, and living area that blends modern elegance with a warm, coastal flair. Bright, breezy, and full of life, it's made for gathering, creating, and enjoying the Florida lifestyle. Whether sipping morning coffee or hosting a sunset dinner, it invites comfort and conversation. Wall-to-wall windows and glass doors frame lush greenery, making you feel as though you're dining in a tropical treehouse. With sliding glass doors opening to the outdoor patio, guests will enjoy this space designed for dining, lounging, and soaking in the lush, tropical surroundings.brbrThe bedrooms exude peaceful serenity. The primary suite is a peaceful retreat tucked away on the second floor. Featuring a plush king-sized bed, the room is bathed in natural light from large windows overlooking lush greenery. A sleek ceiling fan and wall-mounted TV provide comfort and convenience, while the ensuite bathroom offers a private spa-like experience, complete with modern finishes and thoughtful touches. Charming and cozy, the guest bedroom features a comfortable queen-sized bed with soft bedding and tranquil decor. Brightened by natural light and accented with coastal details, the space includes a flat-screen TV, making it a perfect haven for relaxation after a day at the beach. The third bedroom offers two twin beds, ideal for kids, friends, or additional guests. Light and airy, the room includes a TV and playful coastal accents that reflect the home's beachy personality. It's a welcoming and comfortable space for winding down and recharging. For added convenience, there is a full sized sofa sleeper.brbrThe rooftop deck is a private oasis—an inviting retreat perched above the treetops, blending comfort, style, and nature in perfect harmony. With cozy wicker lounge seating under a modern pergola and plush cushions for relaxed conversation, it's the ideal setting for evening gatherings or peaceful morning moments. The open-air section features a pair of loungers and a café table, perfect for soaking in the sun or enjoying a glass of wine under the stars. Surrounded by lush greenery and cooled by coastal breezes, this tranquil perch invites relaxation, reflection, and a deep connection to nature..brbrThe covered poolside dining area offers the perfect blend of comfort and tropical ambiance, ideal for relaxed outdoor living. Featuring a spacious dining area with seating for eight, it invites al fresco meals and sunset cocktails surrounded by lush greenery. Just steps away, the private pool shimmers invitingly, framed by tropical landscaping and complemented by a paved deck with loungers—perfect for sunbathing or a peaceful afternoon by the water. The hot tub offers a perfect spot for relaxation, allowing guests to unwind in warm, bubbling water after a day of exploring. Whether you're entertaining or unwinding, this outdoor retreat is designed for pure vacation bliss.brArts and Vines is a dog friendly home! If you have added a pet to your reservation under the number of pets, the fee of $150 per dog plus tax has been added to your reservation total. Please note, there is a 2-dog limit. Small Dogs Only.brbrIf you are looking for Gulf breezes, peaceful ambience and total relaxation, Arts & Vines is the perfect vacation spot for you.brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - Queen Bed, TV - Floor 2brBedroom 3 - Two Twin Beds, TV - Floor 2brFull Sized Sleeper SofabrbrPlease note:brThis home requires stays of at least 28 nights.brAmenities are subject to change.brSmall Dogs Only - 2 maxbrDriveway parking is available for a maximum of 5 cars. Parking for additional vehicles is not available.brGarage is not available for guest use.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than 28 nights. The maximum occupancy is six. brRRR-00499 brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Arts & Vines: LBK Pool Spa Dog Friendly by Anna Maria Life Vacation Rentals

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$498.0

Make yourself at home in this large recently remodeled 4-bedroom 3 bathroom Longboat Key retreat with 1 king bed and 3 queen beds, this house offers a perfect blend of comfort and style, relax in the large family living space with 65 inch tv and a pool table or take in the fresh beach air on the outdoor patio with plenty of seating and a gas bbq. Plenty of off-street parking. Guests also have free access to Cedars East Tennis resort during their stay (no additional fee) - tennis/pickleball/pool/bar/restaurant and bike rental! Within 200 yards of the house there is a cafe and a deli, 3 pub/restaurants, a pizzeria and a local beach shop.

4-bedroom house on Longboat Key with beach only 150 yards away.

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$333.64

Located on a most welcoming friendly street. This house with 3 bedrooms & 3 full bathrooms sits on a canal with dock and large paved area. Just a short 5 minute walk to the beach and Gulf of Mexico with its amazing sunsets. The perfect place to come and relax on the back open patio with a high top table or on the dock itself with seating. The front patio with seating is partially enclosed if you need a break from the sun and also where the grill is located.brbrThis contemporary home is all renovated with all updated stainless appliances. The perfect place to come and relax. House is well stocked with all the essentials you need inside as well as beach supplies, such as beach towels, beach chairs and a cart to haul all your beach needs, as well as fishing poles and supplies to try your luck fishing off the dock.brbrThe home is a short walk to relaxed and upscale restaurants and Durante Park or a short drive to St. Armands Circle that is full of restaurants and shopping.

Piece of Paradise

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$534.66

Welcome to paradise! This tropical island retreat is located in a quiet residential area on the north end of Longboat Key. Walk to some of the island's best restaurants including Shore, Mar Vista, and Whitneys. Enjoy kayaking, paddleboarding, fishing and boating from the bayfront community dock and boat ramp. Best of all, take a short stroll to one of the most pristine beaches on the island, where you can enjoy sugar sand, clear blue water and breathtaking sunsets.brbr5 MINUTE WALK TO BEACH!!brbrThe upper level of the home is decorated in a casual beachy theme featuring a bright and airy living/dining area with a vaulted ceiling, skylights, and fireplace. The well appointed kitchen has a four seat breakfast bar and its own skylight. brbrThe outdoor areas of the home make it a true tropical paradise. Catch the ocean breezes and savor your morning coffee on the upper level patio surrounded by lush palm trees, as you enjoy watching local parrots, ospreys and peacocks. Down on the pool deck, bask in the Florida sun and splash or swim laps in the extra large pool, or soak your cares away in the attached jacuzzi. Grill out and enjoy outdoor living with family and friends in the covered dining area by the pool. Time to chill out The pool area also features an air conditioned cabana/rec room with large screen TV, refrigerator, seating area and full bathroom with shower.brbrRelax in the two spacious master suites decorated with breezy island flair. Each features a king bed, walk in closet and en suite full bathroom with tub/shower as well as a seating area with comfortable armchairs. The third bedroom has a full size bed, walk in closet and ensuite full bathroom with a walk in shower. All bedrooms have a large screen TV and views of the pool and garden areas.brbrAdditional amenities in the home include a full size washer/dryer, sand shower on the pool deck, and beach chairs and umbrellas. 5 minute walk to the beach with included beach cart.

Peacock Place LBK - Gorgeous 3-bedroom house in Longboat Key

Longboat Key, Florida, United States

3

Bed