Home Vacation Home Rentals By Owner In Longboat Key, FL

Showing 60 Of 150 Vacation Rentals
Slider Thumb

$394.57

/ Nightly
Private Vacation Home

Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA

Longboat Key, Florida, United States

Experience this peaceful beach vibe at the Dolphin's Den in Longboat Key located in a clean, quiet private cul-de-sac. Just a short walk from the private pristine beach on the north end of Longboat Key, sits this beautiful Seaside home. The Dolphin Den Beach Home offers an open, airy, contemporary flair with panoramic Gulf and Bay views from its private rooftop Crow's Nest deck. The exquisite interior design and detailing are evident from the moment you enter the home which features 4 inviting levels and a private outdoor shower to rinse off after a beach day! brbrbrbrThe 1st level opens into an elegant foyer overlooking your private and tranquil Zen Garden, the perfect retreat for relaxing and enjoying the morning breezes. This home is also equipped with a private shower to rinse off after a day at the beach.brbrbrbrThe 2nd level leads into an open floor plan with a high ceiling living/dining combination with Canadian Maplewood flooring throughout, and an abundance of windows allowing all the natural light and beauty of the mature landscaping to shine through. The kitchen is adorned with granite countertops, stainless steel appliances, wood cabinets, and an oversized island for additional seating and entertaining. There are 2 built-in desks for additional office space. The master bedroom suite is large enough for a comfortable sitting area, 2 walk-in closets, seagrass carpets, custom woven shades, and a master bathroom with dual sinks, separate glass shower, and a spa soaking bathtub for the ultimate relaxing experience. brbrbrbrThe 3rd level makes a perfect guest bedroom/office or study, surrounded by windows as well as a hideaway 1/2 bath. brbrbrbrFive outdoor living areas surround the property, including 3 separate decks for entertaining or just enjoying the ocean breeze. The community lap pool and clubhouse are just steps from your back door giving the feeling of your own private pool area. brbrbrbrThe 4th level is your large, private rooftop deck with 360 degrees views from Gulf to Bay, allowing you to capture our magnificent Florida sunsets. This luxury, beach community is truly unique and only blocks away from the historic Village on LBK offering fabulous dining and cultural activities.br brbrbrAccommodations: 3 bedrooms, 2.5 bathroomsbrbrbrbrLocation: 323 Firehouse Lane, Longboat KeybrbrbrbrAmenities: 3 Minute Walk to Beach, Foyer overlooking Private Zen Garden, Private Outdoor Shower, 1-Car Garage, Large Kitchen with Dining Island, 55 TV (streaming services only) in Living Room, Propane Grill on Deck, Stackable Washer/Dryer, Office Desks, Jacuzzi Tub in Master Bedroom, Walk-In Closets, Guest Sleeper Sofa, Outside Decks on all 4 Levels, Wireless Internet, 4 Bicycles, Community, Clubhouse, Walk to Beach, Private Rooftop Deck with Panoramic Gulf and Bay ViewsbrbrbrbrBedding: 1 King, 2 Queens, 1 Sleeper/SofabrbrbrbrView: Bay ViewsbrbrbrbrMinimum Night Requirements: MonthlybrbrbrbrPets Considered: Max Weight 30 lbs. brbrbrbrAssociation Requirements: $250 Fee + Application
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(52)

$515.6

/ Nightly
Private Vacation Home

Limited Time Deal 45% Discount - Best Value on LBK

Longboat Key, Florida, United States

New to market! Introductory pricing. Premium dates available.brPet friendly single family home located in the quiet residential neighborhood of Sleepy Lagoon on the north end of Longboat Key. This home is directly on the water with a 60' wide saltwater canal in the backyard. Manatees, pelicans and jumping mullet are frequent visitors. brIf you love the beach, it's a 7 minute walk to one of the most pristine beaches in Florida. The sand is like powdered sugar because it is 99% pure quartz. The house is immaculately clean and well appointed. We provide comfy beds, high quality linens and a fully stocked kitchen. People love the indoor/outdoor living on the spacious back deck or in the screened front pool area. brbrOne level living, spacious and comfortable. Fantastic views abound through gigantic living room picture window plus 3 full sized sliding glass doors overlooking canal. It's like living in a nature sanctuary with manatees, egrets and tons of fish as frequent visitors. brSpacious back deck. Screened in front porch with comfy seating overlooking a fantastic swimming pool. High quality mattresses, crisp linens and a well stocked kitchen. We've tried to think of everything so you have all the comforts of home. brHigh Def Smart TVs, Lightning Fast WiFi Internet, granite counter tops and stainless appliances, fully stocked with amenities such as; paper goods, beach towels, beach chairs and umbrellas, laundry detergent, etc. brbrLiterally tons of stuff to do on Longboat Key:br• Beautiful powder sugar sand beaches to view the world's greatest sunsetsbr• Scenic walking/biking paths including Pet Friendly Durante Park and Nature Preservebr• World class fishing, rent a boat from Cannon's Marina 1 mile awaybr• Bring your own boat, very nice free public launch less than 1 mile away. br• Wide variety of fantastic restaurants in the immediate area.br• Play Tennis at Bayfront Park or at Cedars Hartrue Clay Tennis Courtsbr• Year round golf at several public courses in the areabr• Art festivals, cultural events and wine tastings almost every weekendbr• Ideally situated halfway between St. Armand's Circle and Anna Maria Island.br• Wild peacocks roaming the streetsbr• Super friendly neighborhood, a boat load of really nice people.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(3)

$349.01

/ Nightly
Private Vacation Home

Beautifully Decorated 2 BR Townhome - Cedars East #802 by RVA

Longboat Key, Florida, United States

Cedars East Tennis Resort – Unit #802 | Longboat Key Vacation Rental by RVA Resort VacationsbrbrEscape to paradise at Cedars East Tennis Resort, a premier Longboat Key vacation rental destination by RVA Resort Vacations. Nestled along Florida’s Gulf Coast, this peaceful resort offers the perfect blend of relaxation, recreation, and modern comfort.brbrUnit #802 is a beautifully remodeled 2-bedroom, 2.5-bath tri-level townhome featuring elegant coastal décor and serene garden and water views from the primary bedroom and den. Enjoy a full-size kitchen with stainless steel appliances, a spacious living and dining area and a den with room to work, if necessary. This rental includes a private 1-car garage, easy access to local beaches, and proximity to Sarasota’s shopping, dining, and attractions. Whether you’re seeking an active tennis retreat or a relaxing coastal escape, Cedars East by RVA Resort Vacations delivers the ultimate Florida getaway experience.brbrGuests have access to exceptional resort amenities, including a junior Olympic-sized heated pool, tennis and pickleball courts, a modern 24/7 fitness center, and scenic boardwalks that connect The Gardens, Club Level, and Preserves sections of the resort.brDiscover 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.brbrHere, 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.brbrAccommodations: 2 Bed + Den and 2.5 BathsbrbrBedding: 1 King, 1 Full, 2 Twin Bunk Beds and Sleep Sofa in DenbrbrAddress: 802 Evergreen Way, Longboat Key FL 34228brbrClub and Recreation Facilities: brTennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brFitness Center - Modern, 24/7 accessible fitness center with secure access. brBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrDining 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. brClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. Onsite Tennis Director available for clinics or private lessons.brbrFishing 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. brbrBeach 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.brbrMinimum Night Requirements: Minimum Stays Apply
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$269.51

/ Nightly
Private Vacation Home

Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA

Longboat Key, Florida, United States

Welcome to Hy Tee, a charming coastal retreat nestled on Longboat Key, Florida. This beautiful vacation home promises a seamless blend of relaxation and convenience, situated just a short walk from the pristine beaches of the Gulf of Mexico. Whether you're here for a tranquil getaway or a base to explore the local treasures, Hy Tee offers everything you need for an unforgettable stay.brbrbrbrAs you enter the home, you’ll be greeted by a well-appointed kitchen, complete with modern appliances and ample space for preparing your favorite meals. The kitchen flows naturally into a cozy, open living area, perfect for unwinding after a day in the sun. For those who prefer outdoor cooking, a gas grill is available on the pool deck, making it easy to savor a delicious barbecue while soaking up the Florida sunshine.brbrbrbrOne of Hy Tee’s highlights is its private, heated pool, where you can enjoy a refreshing swim at any time of year. The pool deck is spacious and designed with comfort in mind, providing plenty of space to relax, sunbathe, or read a book in the fresh coastal air. To make your beach days even better, the home comes with bicycles for guest use, allowing you to explore the island at your leisure.brbrbrbrWith wireless internet and a washer/dryer on-site, HyTee ensures you’ll have all the comforts of home. When you’re ready to explore beyond the property, you’ll find yourself conveniently close to St. Armand’s Circle, a vibrant hub filled with boutiques, dining, and entertainment options.brbrbrbrIdeal for a serene beach getaway or an active exploration of Longboat Key and its surroundings, Hy Tee is the perfect retreat for every type of traveler.brbrbrbrAccommodations: Two-bedroom, two-bathroombrbrbrbrAmenities: Pool Deck, Bikes For Guest Use, Private Heated Pool, Gas Grill, Kitchen, Wireless Internet, Beach Access within Walking Distance, Close Proximity to St. Armand's Circle, Washer/DryerbrbrbrbrLocation: 1200 Bogey Lane, Longboat KeybrbrbrbrBedding: 2 Kings, 1 Queen Sleeper SofabrbrbrbrView: Neighborhood ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrOther: Additional electric and/or pool heat charges may apply; please call our local offices for details.brbrOne small-medium size dog considered- fees will apply. Please contact RVA for more information.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb

$803.22

/ Nightly
Private Vacation Home

637 Norton - Longboat Key - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people.

Longboat Key, Florida, United States

637 Norton - Longboat Key - 4 Bedroom/ 3.5 Bath, maximum occupancy of 8 people.br Canal Home - Private Pool - Boat Dock - Distance to the Beach: 1 blockbr br Live the Florida lifestyle in this beautiful, comfortable home located in the Sleepy Lagoon.br This home is wheelchair accessible. br br Complete and total luxury, offering a secluded, back deck and heated pool. Also enjoy your own private dock on a deep-water canal, leading right out to Sarasota bay.br The local's access to the beautiful beaches of Longboat Key, is only a short walk away.br br The main living level includes a modern kitchen with GE Monogram appliances and two separate sitting areas with a dining area seating 10 people. Sliding doors open up onto the porch and barbecue area.br br The master suite is located one floor up with an en-suite master bathroom including a cooler, shower and jetted tub. Next to the master suite is a guest bedroom with a king size bed.br br 4 Bedrooms, Sleeps 8br Bedroom 1 - 1 king, 1 sleeper sofa/futon br Bedroom 2 - 1 king br Bedroom 3 - 1 king br Bedroom 4 - 1 king, 1 sleeper sofa/futonbr br 3 Bathrooms, br 1 Half Bathbr Bathroom 1 - toilet, shower, jetted tub, bidet br Bathroom 2 - toilet, shower br Bathroom 3 - toilet, shower br Bathroom 4 - toilet br br A little over ten miles long, Longboat Key is a barrier island between Sarasota Bay and the Gulf of Mexico. The home's central location makes it easy to explore the area. Head south to see Mote Marine and to check out the shops and restaurants on St. Armands Circle. Head on a bit further, and you are part of the Sarasota scene. Venture north , and cross the bridge to have a look at Anna Maria Island, Bradenton, and more.br br Pool heat is available for $25.00 per day. 1 week minimum.br br You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 4+br - Bed Sizes: K,K,cal Kin master,kbr - Sofa Sleeper: yes-denbr - # Baths: 3.5br - Balcony: Yes and BBQbr - Pool: Private poolbr - Pool Heat Avail: Y-at cost of propanebr - #of units in complex: 1br - BBQ Grill: yesbr - Square Feet: 3654br - Floor Number: 2 STORY HOMEbr - Distance to Beach: 1 blockbr - Internet: wifibr - View: CANALbr - Elevator: Yes-PRIVATEbr - washer dryer: in unitbr - Dishwasher: Yesbr - Boat Dock: Ybr - Maximum Persons: 8br - DVD/VCR: Yesbr - TV: yesbr - Phone: yesbr - Hairdryer: yesbr - Type of Parking: GARAGE/DRIVEWAY
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(22)

$222.77

/ Nightly
Private Vacation Home

Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5

Longboat Key, Florida, United States

Cedars Tennis Resort, is a luxury vacation rental on Longboat Key, close to Sarasota and world renowned St Armand's Circle. This spacious 1440 sq ft townhouse includes a 1 car garage on the ground floor, kitchen, half bath and spacious living room/dining room on the first floor that includes a sleeper sofa. There are two bedrooms on the 2nd floor, the master bedroom has a king bed the guest bedroom has twin beds (can be pushed together to make a full size bed) each bedroom has it's own full bath. There is also a rollaway bed which can be used if required. There is a screened in back lanai with a relaxing tennis court view. Enjoy a Gulf horizon view from the living area. The location is perfect with world class restaurants and Harry's Convenience store within walking distance. There are public beach accesses within a few miles in either direction with the beach being just across the street, bike trails in front of the complex with Sarasota Bay on the opposite end of the property with a beautiful bay view and fishing pier available for guests. Must be 25 or older to rent. Guests will have use of the junior Olympic pool included in rental fee. The tennis club and health & fitness facilities can be used by purchasing a temporary membership if required. The unit has recently had all new windows and sidings replaced and the lounge and dining area have been refurnished. The kitchen has just been remodelled with new quartz counter tops and Shaker style doors. The unit is fully equipped with everything needed by a family including stair gates, high chair, travel cot etc. and numerous toys and games as well as a BBQ are located in the garage.brThere is an excellent onsite restaurant, Hugo's 2, which serves freshly cooked dishes in a relaxing indoor and outdoor setting.
Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps

Slider Thumb
Exceptional(7)

$346.68

/ Nightly
Private Vacation Home

Tranquil Bay Views – Cedars East #812 by RVA

Longboat Key, Florida, United States

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 #812 Accommodations: 2-bedroom, 2.5 bathroom townhome with views of the bay and preserve from your private patio.brbrbrbrUnit Amenities: 1-Car Garage, Wireless Internet, Full-size Kitchen, Private Patio, 24/7 Fitness Facility, Community Pool, Beach Access (A Short Distance Away), Full Club access to Cedars Tennis ResortbrbrbrbrLocation: 812 Evergreen Place, Longboat KeybrbrbrbrView: Bay ViewbrbrbrbrBedding: 1 King, 1 QueenbrbrbrbrMinimum Night Requirements: Minimum Stays Apply
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$355.26

/ Nightly
Private Vacation Home

Cedars East 2BR Condo – Unit #611 by RVA

Longboat Key, Florida, United States

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrDiscover 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.brbrHere, 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.brbrAccommodations: 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).brbrClub 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. brbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrDining 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.brbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrFishing 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. brbrBeach 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.brbrResidential 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.brbrUnit #611 Accommodations: Recently remodeled 2-bedroom, 2.5-bathroom town home with preserve views from your private lanaibrbrUnit Amenities: Wireless Internet, Full-size Kitchen, Washer/Dryer in Unit, Private Lanai, Fitness Facility, Community Pool, Pets Considered, Beach Access (A Short Distance Away).brbrLocation: 611 Cedars CourtbrbrView: Garden ViewbrbrBedding: 1 King, 1 Queen, 1 Twin XL Bunk, 1 Sleep SofabrbrMinimum Night Requirements: Minimum Stays ApplybrbrPet Policy: Pets Allowed- Fees Apply
Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps

Slider Thumb

$317.05

/ Nightly
Private Vacation Home

Direct beachfront private home by FVC

Longboat Key, Florida, United States

A beachfront home that will delight, professionally managed and offered by FL Vacation Connection.brbrA full home-length screened porch with tile floors, palm-frond ceiling fans and enough furniture to set up shop for the duration of vacation greet you at Tropical Odyssey. The sweeping views of the azure Gulf are simply breathtaking. Your own path brings you down to the sand and the crystalline warm waters. Can you smell the salt in the air brbrAs you enter Tropical Odyssey, you are greeted by a lovely foyer complete with a sofa. Let this be your special quiet space for reading or just relaxing. A soaring living room decorated in neutral colors and a tropical motif is a large and welcoming room, with a beautiful wall mural depicting the tropical scene just outside your door. Sure to be the scene of many family gatherings, there's plenty of space for everyone. The view is divine and a flat screen TV and DVD can provide hours of entertainment. brbrOpen the sliding glass door to the wonders of nature! The sweeping views of the Gulf will captivate your mind and spirit. Make sure to plan your evenings so as not to miss the magnificent sunset over the water. In the cool, early morning, walk the few feet down your path and put your toes in the sand. Perhaps take a long beach walk in search of treasures from the sea. brbrThe beautifully equipped kitchen will be a pleasure to cook in. Plenty of cabinets ensure plenty of space for all of your family's goodies. Lots of counter space means lots of prep space and later, buffet space for your favorite meals. The warm wood cabinets, cool tile floors and pretty tiled backsplash create a welcoming environment for the family chef. brbrThe adjacent dining room and breakfast bar can accommodate a family of 6. Open the sliding glass door and you'll double your space with another table for 6 on the lovely screened porch. With all this room, your family can easily enjoy meals together as you talk and laugh about the adventures you've enjoyed and make plans for those yet to come.brbrWith four en-suite bedrooms, everyone can have their own personal space and enjoy some privacy. It's the perfect way for the family to vacation together! On the main level, is a Queen bedroom suite with a sitting area. On the upper level are two additional Queen bedroom suites, one with a sliding door to the upper-level balcony, and a suite with two Twins. brbrTropical Odyssey is a magical vacation home that will leave your family with a treasure trove of happy memories. Call today to book this special property and start planning your Longboat Key adventure!brbrTown of Longboat Key RRR-00201.2025
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

Slider Thumb

$366.14

/ Nightly
Private Vacation Home

Morningside Retreat Home by RVA

Longboat Key, Florida, United States

Welcome to the Morningside Retreat, a beautifully appointed Sarasota getaway designed for relaxed coastal living with a refined, modern touch. Nestled in a quiet residential setting, this inviting escape offers the perfect balance of comfort, style, and convenience—ideal for guests seeking a peaceful stay close to everything Sarasota has to offer.brbrInside, the home features bright, open living spaces filled with natural light, thoughtfully curated furnishings, and a calming coastal aesthetic throughout. The living area flows seamlessly into a fully equipped kitchen, complete with modern appliances, ample counter space, and everything needed to prepare meals at home. Whether you’re enjoying a quiet morning coffee or gathering for dinner after a day at the beach, the space is designed to feel both functional and welcoming.brbrThe 3 bedrooms are comfortably styled with soft linens and a serene atmosphere, offering a restful retreat after sun-filled days exploring the area. 2.5 Bathrooms are clean, modern, and well-appointed, providing hotel-like comfort with a residential feel.brbrStep outside to enjoy Florida’s signature indoor-outdoor lifestyle. Whether it’s lounging with a book, enjoying an evening drink, or simply soaking in the warm breeze, the outdoor space offers a peaceful setting to unwind and recharge.brbrThe beach is just a short stroll away—typically about a 2 to 5-minute walk—this property includes gated, deeded access to a private section of Lido Shores Beach.brbrConveniently located near Sarasota’s best beaches, dining, shopping, and cultural attractions, The Morningside Retreat places you within easy reach of everything while still offering a quiet place to return home to. From Lido Key’s world-famous sand to downtown’s vibrant arts scene, everything is just a short drive away.brbrPerfect for couples, small families, or extended stays, The Morningside Retreat is your stylish Sarasota home base for relaxation, exploration, and effortless coastal living.brbrAccommodations:brbrLocation: 1173 Morningside Place Sarasota, FL 34236brbrBedding: 1 King in Primary, 2 Twins in Guest, 1 Queen and 1 Bunk Bed in GuestbrbrView: BackyardbrbrMinimum Night Requirements: 1-Month MinimumbrPets considered by owner- please contact Reservations for additional details
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(9)

$295.42

/ Nightly
Private Vacation Home

Tennis Tranquility-Cedars East #519 by RVA

Longboat Key, Florida, United States

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 #519 Accommodations: 2-bedroom, 2.5 bathroom town home with garden views from your private patio. This unit also accepts pets (with restrictions) so bring the whole family for a warm escape to Florida.brbrbrbrUnit Amenities: 1-Car Garage, Full-Size Kitchen, Wireless Internet, Private Patio with Garden Views, Keyless Entry, Pets Considered, Fitness Facility, Community Tennis Courts, Community Pool, and so much more.brbrbrbrLocation: 519 Forest WaybrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, 1 QueenbrbrbrbrSleeper sofabrbrbrMinimum Night Requirements: Minimum Stays Apply
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(9)

$295.04

/ Nightly
Private Vacation Home

Weekly / Monthly Rental - Spacious Condo In Longboat Key Resort Close To Pool, Tennis And Beach!

Longboat Key, Florida, United States

VACATION RENTAL - SPACIOUS TOWNHOUSE IN LONGBOAT KEY TENNIS RESORT CLOSE TO POOL AND BEACH! Located in the beautiful Cedars East Tennis Resort property, this 1440 s. f. 2-bedroom, 2-bath townhouse is just steps away from the Junior Olympic-sized heated Resort pool. Views of tennis courts with a beautiful view over a lush green conservation area from the exterior screened porch. This comfortably spacious open concept floor plan is well designed with 9' ceilings, easy-care flooring and ...living, dining and kitchen on the main floor, and bedrooms and bathrooms upstairs for privacy and comfort. NO PETS / NO SMOKING.brbrThe property is quiet, but close to everything you would want for a get-away. Longboat Key is close to Sarasota and world renowned St. Armand's Circle. The location of this townhouse condominium is close to several restaurants from pizza to fine dining, and Harry's convenience store and deli is within walking distance. Public beach access is less than a mile in either direction with the beach located directly across the main road. Boardwalks and bicycle trails run throughout and alongside the Resort. Sarasota Bay is a short walk along the boardwalk and Bayside pathway with beautiful Bay views and fishing pier available.brbrOther Amenities: 1 car garage, additional parking, cable flat screen TVs in living room and master bedroom, high speed Internet, property management company located on Longboat Key and available 24/7. Access to heated junior Olympic pool is included. Tennis, fitness and community bike rentals are available with a temporary membership for purchase separately. Incredible beaches, fishing and kayak rentals located just a block or two away as well as shopping and restaurants that all provide the perfect Longboat Key vacation destination!brbrAppliances/Equipment: Built In Oven, Dishwasher, Garbage Disposal, Washer and Dryer, Microwave, Oven, Range, Refrigerator. brbr*Prices shown are based on 4-person occupancy. Additional persons staying in the unit for a period of longer than 7 days may be considered additional occupants and subject to additional rental fees being charged. Your rental Agent must be advised of all additional occupants and dates they will be in the unit. 7-night minimum stay. Maximum occupancy 4 persons. brbrRates include all utilities including WIFI. Additional charges will be departure cleaning fee ($175), Booking fee ($50), Sales and Resort Taxes (12%) and Travel Insurance (if requested). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.brbr* If booking over a Holiday time frame Holiday rates may apply. *brbrContact Wagner Realty *****brbrAmenities Include:brbr- View: Clubhousebrbr- Beach Distance: Closebrbr- Pool, Heated: Yesbrbr- Pool: Jr. Olympicbrbr- TV Cable/Satellite: Cablebrbr- washer dryer: In-unitbrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: Twinsbrbr- Parking: Garage enclosedbrbr- Lanai: Enclosed Screenedbrbr- TVs/VCR/DVD: Flat screen TVbrbr- Furnished: Turnkeybrbr- Exercise Facility: Additional Feebrbr- Master Bath Features: En-suite tub-showerbrbr- Walk-In Shower: Guest bathbrbr- Community Features: Fitness-tennis extrabrbr- Garage: Enclosed Oversizedbrbr- Tennis: Available for feebrbr- Bus Service Avail.: MCAT - Trolleybrbr- Agent: Gregory Kossbrbr- Office: Longboat Keybrbr
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$159.89

/ Nightly
Private Vacation Home

Longboat Key tennis resort minutes to beach - Ospreys Nest

Longboat Key, Florida, United States

Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island's most sought-after tennis resorts—offering a unique blend of tropical charm and resort-style amenities like Har-Tru courts with expert instructors and an olympic sized pool.brbrStep into island living with the second floor as your main living space, thoughtfully designed for comfort and connection. Relax on the queen-size pull-out sofa, or step out onto the screened-in lanai where you can sip your morning coffee while soaking in the serene, lush surroundings. The dining area comfortably seats up to seven, making it the perfect setting for family meals and lively conversations. Just adjacent, the kitchen offers four barstools, ample counter space, and all the essentials for preparing your favorite family dishes and beach-day snacks.brbrUpstairs, the third level features both bedrooms. The primary bedroom is a true retreat, featuring a king-size bed, breathtaking views of the tropical landscape, and an attached, spa-inspired bathroom with dual vanities and a spacious walk-in shower. The second bedroom includes a queen-size bed with a twin trundle, a TV, and generous closet space—ideal for guests or kids to unwind in comfort.brbrWhat truly sets this home apart is the incredible Cedars East community. Located on the bay side of Longboat Key, Cedars East offers a lifestyle like no other—with a heated junior Olympic-size pool, tennis courts, boardwalks through mangrove-lined nature trails, bike paths, and a bayside fishing pier. You'll love the lush, well-manicured grounds, and how close you are to the gulf beaches, boutique shopping, and local dining that Longboat Key is famous for.brbrWhether you're planning to spend your days exploring the beach, relaxing poolside, or simply enjoying the peace and beauty of the natural surroundings, this charming Cedars East getaway is the perfect island retreat.brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties.brbrFurry friends welcome! Up to 2 pets allowed. A non-refundable pet fee applies and must be paid directly to the management company.
Bed 2

Bed

Bath 2

Bath

Sleep 7

Sleeps

Home Most popular vacation rentals in Longboat Key