34228, Florida, United States Vacation Rental Homes By Owner

$350.61

Gulf of Mexico Beach Front ....Walk out condo steps from the private beach!!!

Longboat Key, Florida, United States

Beautiful main floor two plus bedroom condo with stunning views of the Gulf! Never miss a sunset, watch from the condo or walk out to the private beach. Eight Clay tennis courts, four pickle ball courts. Open play at 9am and 2pm daily. Two beautiful heated pools, jacuzzi, workout room, sauna and club house for entertaining and socializing.

2

Bed

2

Bath

6

Sleeps

Select Dates for Price

Condo

OceanVista Beachfront Retreat

Longboat Key, Florida, United States

Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath condominium boasts a stylishly designed interior that is sure to impress. Experience tranquility in the master bedroom, which offers exquisite bedding and a sitting area with a stunning view of the azure waters. The ensuite master bath provides the perfect sanctuary for relaxation. The gourmet kitchen with stainless steel appliances is perfect for entertaining and the light and bright living room features exquisite seating and state-of-the-art digital components, including a 75-inch TV and DVR. Stay connected with dedicated desk space, a washer and dryer, and Wi-Fi. Large-screen smart TVs are also available for your added enjoyment. Take advantage of resort-style amenities including a gulf-side heated pool, har-tru tennis court, updated social room, state-of-the-art fitness area, and storage for kayaks, paddleboards, and bikes. Conveniently located to shopping, dining, St. Armand’s Circle, downtown Sarasota, and the Arts, this vacation rental has everything you need for a truly unforgettable stay. Don't miss out on this opportunity to live the life you've always imagined!

Bed

Bath

Sleeps

$233.6

/ Nightly

Apartment

Beachside Studio – Silver Sands #253A, Longboat Key

Longboat Key, Florida, United States

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 #253A 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, fishing pier 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 #253A Features: Hotel room in the Green BuildingbrbrbrbrBedding: 1 QueenbrbrbrbrResort 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

1

Bed

1

Bath

2

Sleeps

$265.94

/ Nightly

Condo

Whitney Beach #335, 1 BR /1 BA beach front condo by RVA

Longboat Key, Florida, United States

Whitney Beach 335 – Gulf-View Retreat on Longboat KeybrbrWelcome to Whitney Beach 335, a charming coastal getaway with stunning views of the Gulf of Mexico and a truly unique sleeping layout. This inviting condo offers a peaceful escape with all the comforts you need for a relaxing stay on beautiful Longboat Key.brbrThe primary bedroom features a comfortable king-size bed, creating a private retreat after a day in the sun. The entryway includes two built-in twin bunk beds, perfect for kids, extra guests, or anyone who loves a fun and functional sleeping space.brbrStep out to the open-air patio and take in the breathtaking Gulf views, where you can enjoy your morning coffee, watch unforgettable sunsets, or simply listen to the soothing sound of the waves. The bright, open living area makes it easy to unwind, dine, and spend quality time together.brbrGuests of Whitney Beach enjoy direct beach access, lush tropical grounds, and a serene, laid-back atmosphere just minutes from shopping, dining, and local attractions.brbrWhether you’re planning a family beach vacation or a quiet coastal retreat, Whitney Beach 335 offers a memorable stay in one of Longboat Key’s most desirable beachfront communities.brbrAccommodations: 1-Bedroom, 1-BathroomsbrbrAmenities: Gulf Views, Full-size Kitchen, Open Patio, Wireless Internet, Washer/Dryer in Unit, Community Pool, Community Tennis Courts, Deeded Beach AccessbrbrLocation: 6701 Gulf of Mexico Drive #335, Longboat KeybrbrBedding: 1 King, 2 Bunk BedsbrbrbrView: Gulf ViewbrbrMinimum Night Requirements: 1 Month brbrAssociation Requirements: $75 + $25 Association Fee Application, $25 for background check made out to LPM due once every 5 years for repeat guests.

Bed

Bath

Sleeps

$222.26

/ Nightly

Condo

Charming Longboat Key Bungalow minutes from beaches, restaurants, parks

Longboat Key, Florida, United States

Looking for an “island style getaway” this is it! Public beaches minutes away or head next-door to the beautiful Durante park on the bay.brThis newly renovated marvelous “cottage like” condo in Longboat Key is a cozy bungalow for guests looking to unwind and relax. The upscale feeling beachy bedroom features a nice queen bed, perfect for a restful night's sleep. With WiFi, a washing machine & dryer and AC, guests have everything they need for a comfortable stay including 2 beach chairs & beach towels. When you return from the beach, you are welcome to use the refreshing outdoor shower! Don’t forget to also relax on our outside patio areas with your favorite drinks…Come experience the enchanting charm of this condo and create unforgettable memories in Longboat Key. Book with us now & fall in love with the area and enjoy the magic it has to offer. Pets are not allowed on this premises.

1

Bed

1

Bath

2

Sleeps

$452.0

/ Nightly

Condo

2 Br/2Ba Gulf Front Condo w/ private beach access, on Long Boat Key, Florida

Longboat Key, Florida, United States

Discover the beauty of Longboat Key from this 2-bedroom condo. Beautiful, 2 Br/2Ba renovated Gulf Front Condo with gorgeous morning light and private beach available for rent on Long Boat Key, Florida. Steps to the pool and sand, kayaks, Hobie Cat, beach attendant with chairs and umbrellas to serve you. 2 tennis courts, pool, hot tub, bicycles, ping pong table and community room/workspace. The perfect place to vacation in late October. Close to the new St. Regis and across the street from CVS, Publix grocery, nail salon, and restaurants. Enjoy St. Armand's Circle, The Ringling Museum, The Mote Aquarium, as well as theaters and more shopping in nearby Sarasota.brbrThis gorgeous property features 1 queen bed, 1 twin bed, 2 bathrooms with a shower, and a cozy living room with a sofa bed. Enjoyable amenities like WiFi, AC, and a fitness room are available for guests.

2

Bed

2

Bath

6

Sleeps

$474.6

/ Nightly

Private Vacation Home

La Paloma! Fantastic 3-bedroom house with private pool in beautiful Longboat Key

Longboat Key, Florida, United States

Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room with dining are and spacious kitchen will make you feel at home right away. The kitchen is fully equipped for your convenience. Outdoors of this home is even more welcoming and paradise-life. Lush and tropical garden around the beautiful swimming pool, cabana with comfortable seating or other seating areas are there just for our guests. There is plentiful parking spaces in front of the house or next to it. And - the beaches..yes that is what matters. Whitney Beach on Longboat Key, couple minutes of walk. Or you can visit the Beer Can Island, popular place for boats to hang out. Coquina Beach on Anna Maria Island is not far also. La Paloma just has it all! Sweet home with good vibe close to all you need on vacation!

Bed

Bath

Sleeps

$361.46

/ Nightly

Condo

Luxury Gulf-Front Condo on Longboat Key with Breathtaking Sunsets

Longboat Key, Florida, United States

Luxury Gulf-Front Condo on Longboat Key with Breathtaking Sunsets – Portobello Unit #204brbrWake up to sweeping Gulf of Mexico views, step directly onto pristine Longboat Key beach, and unwind each evening with breathtaking sunsets from your private lanai.brThis completely remodeled, luxury Gulf-front condo blends elegant coastal design with modern comfort in one of Longboat Key’s most desirable beachfront communities. Unit #204 offers unobstructed views of the beautiful white-sand beach and the Gulf of Mexico, where breathtaking sunsets paint the sky each evening—best enjoyed from your private beachfront lanai.brbrThis newly renovated two-bedroom, two-bath condo blends refined coastal elegance with modern comfort. Thoughtfully redesigned from top to bottom, the interior features upscale finishes, fresh furnishings, and a sophisticated island-inspired palette that enhances the natural beauty of the Gulf just beyond your doors. Sliding glass doors in both bedrooms and the living area creates seamless indoor-outdoor living and allow stunning beachfront views from nearly every room.brbrThe spacious living and dining areas flow into a fully equipped, full-size kitchen, making this condo ideal for extended stays, seasonal rentals, and luxury island escapes. Guests enjoy premium conveniences including elevator access, in-unit washer and dryer, high-speed wireless internet, and beautifully appointed living spaces designed for relaxation.brPerfectly located along Gulf of Mexico Drive, Portobello places you in the heart of Longboat Key while offering the serenity of a private beachfront retreat. Community amenities include a Gulf-front swimming pool and tennis courts, enhancing the resort-style experience.brbrAs an exceptional added benefit, guests of Portobello Unit #204 receive limited temporary membership privileges at the prestigious Cedars Tennis Resort, featuring Har-Tru tennis and pickleball courts, a Jr. Olympic heated pool, fitness center, and community bicycles—an unmatched luxury for tennis enthusiasts visiting Longboat Key.brWhether you are seeking a luxury monthly beachfront rental, a snowbird retreat, or a peaceful coastal escape, this remodeled Gulf-front condo on Longboat Key delivers stunning views, beautiful beachfront access, and the relaxed sophistication of island luxury.brbrProperty Details:br• Accommodations: 2 Bedrooms | 2 Bathroomsbr• Bedding: 1 King | 2 Twinsbr• View: Direct Gulf-Front Views with Stunning Sunsetsbr• Location: 3235 Gulf of Mexico Drive, Longboat Key, FLbr• Minimum Stay: 1 Monthbr• Association Requirements: $100 Association Fee + $25 Lighthouse Property Management Fee; ApplicationbrbrAmenities:brLuxury Gulf-Front • Completely Remodeled • Private Beachfront Lanai • Elevator • Full-Size Kitchen • Community Pool • Tennis Courts • Washer/Dryer • High-Speed WiFi • Direct Beach Access • Cedars Tennis Resort Membership Privileges

2

Bed

2

Bath

4

Sleeps

$299.54

/ Nightly

Condo

Waves, White Sand & Private Beach at Club Longboat #312 Condo by RVA

Longboat Key, Florida, United States

Welcome to your very own slice of paradise on Longboat Key! #312 at Club Longboat Beach and Tennis Resort is a stunning beachfront condo offering the ultimate coastal living experience, featuring luxurious amenities and breathtaking views of the Gulf of Mexico.brbrbrbrWake up to the soothing sounds of the ocean and step out onto your private patio to enjoy stunning sunrise and sunset views over the Gulf of Mexico. With direct beach access, you can stroll along the pristine shores or take a dip in the azure waters whenever you please.brbrbrbrCommunity Tennis Courts: Tennis enthusiasts will love the convenience of on-site tennis courts. Challenge your friends to a friendly match or work on your backhand, while enjoying the cool sea breeze. brbrbrbrCommunity Pool and Jacuzzi: After a day at the beach or on the courts, unwind in the community pool and jacuzzi. Whether you're seeking relaxation or socializing with fellow residents, these refreshing amenities provide the perfect oasis.brbrbrbrFitness Center: Stay in shape while enjoying paradise. The well-equipped fitness center lets you maintain your workout routine with state-of-the-art equipment.brbrbrbrLongboat Key itself is a serene and upscale community known for its pristine beaches, championship golf courses, and top-notch dining establishments. With miles of white sandy shores, you'll have ample opportunities for sunbathing, beachcombing, or simply enjoying long walks along the shore.brbrbrbrThis beachfront condo offers not just a home, but a lifestyle of leisure and luxury. Don't miss the chance to make this beachfront paradise your own!brbrbrbrAmenities and Club Facilities Include: Longboat Key's finest 8 Har-Tru tennis courts (some lighted for night play), 2 heated community swimming pools, sauna/whirlpool/locker rooms, clubhouse, exercise facility, community propane grill, library, onsite management, tennis professional, beach access, fishing, and bocce ball. Reserve your accommodations for the perfect island vacation!brbrbrbrAccommodations: 3-Bedroom, plus DEN 2-BathroomsbrbrbrbrBedding: 2 King, 1 Queen and 1 sofa bedbrbrbrbrLocation: 5055 Gulf of Mexico Drive #312, Longboat KeybrbrbrbrView: Community Tennis CourtsbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $100 Rental Application Fee

Bed

Bath

Sleeps

$304.43

/ Nightly

Condo

Seaside Suite Silver Sands #247 – 1BR/1BA Resort on Longboat Key, Sleeps 4

Longboat Key, Florida, United States

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, so guests can read email, surf the Internet and soak up the Florida sun all at the same time!brbrAccommodations: 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. brbrUnit #247 Features: 1-bedroom, 1-bathroom unit in the Orange BuildingbrbrLayout Note: Please note, the front door to unit 247 opens into a bedroom space before proceeding into the living areas. We kindly ask guests to take this layout feature into consideration when making their travel selections.brbrView: Pool/Gulf ViewbrbrBedding: 1 King, Sleeper SofabrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Daily Maid Service, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, DVD/VHS Players, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Bed

Bath

Sleeps

$438.01

/ Nightly

Private Vacation Home

Beach Bungalow: Best Canal, Dock, Beach, Pool, Pet Friendly. Renovated in 2025

Longboat Key, Florida, United States

This beautiful and spacious 3 bedroom house underwent a total renovation in 2025, it's brand new. Located on one of the best canals on Longboat Key with quick access to a semi-private beach and Longboat Pass for gulf fishing or cruising within minutes. Longboat Pass is also home to one of the best sand shoals on the west coast to beach up to and hang out all day. brbrThe property has a large heated pool and a new, large dock with space for a 23' foot boat. There is a floating dock which is fantastic for launching and storing kayaks or paddle boards during your stay. To adult bicycles, helmets and locks are provided for guests to use. The beautiful, white sand, semi-private beach is within a 5 minute walk down the street. Bring your boat and enjoy a fantastic time in the sun by the pool, at the beach or on your boat. Other easy boating options include hiring Captain Jim, the neighbor in the house to the left, for sunset cruises or day cruises and renting from nearby Cannon's Marina.

Bed

Bath

Sleeps

$224.28

/ Nightly

Condo

Updated 2B/2B with a beautiful view of the bay!

Longboat Key, Florida, United States

Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views off the patio and from the master bedroom suite. Relax at the condo or stroll to the Gulf side and enjoy the powder white sand on the beach! Close proximity traveling south to St. Armands circle, Mote marine and fabulous restaurants or travel north and visit Anna Maria Island!brbrbr• Carefree check-in, go straight to your unit no office visit required.br• Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker.br• Comfortable living room area w/ a large flat screen TV.br• Washer and Dryer Conveniently located in unit.br• Master bedroom including a king size bed with brand new Tempur-pedic mattress , flat screen TV, walk in shower, walk in closet, and beautiful view of the bay!br• Spacious guest bedroom br• Large Patio overlooking the bay with outdoor seating and a table.brHarbor Villa Club amenitiesbr• Poolbr• Hot Tubbr• Tennis Courtbr• Boat Slips (Rented Separately)br• Covered Parkingbr• ElevatorsbrbrThe Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as

Bed

Bath

Sleeps

Select Dates for Price

Condo

1st Floor Beachfront Luxury–Ocean Views Included Club Longboat #516 by RVA

Longboat Key, Florida, United States

RVA invites you to experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This two-bedroom condo with office/den is located on 750 ft of pristine beach with a private patio facing the Gulf and is ideal for a relaxing getaway. Imagine spending your days lounging by the community pool, enjoying a game of tennis, or sipping margaritas during an unforgettable Gulf sunset. brbrbrbrClub Longboat Beach and Tennis Resort has been a long-time iconic gem on Longboat Key. From a beautiful Gulf front beach, to 8 Har-Tru tennis courts, 2 pools, clubhouse, and social activities, it’s all here to enjoy. Club Longboat is situated in close proximity to St. Armands Circle and the City of Sarasota, a well-known center for Arts and Culture including the Asolo Theater, Van Wezel Performing Arts Center, and Ringling Museum.brbrbrbrThe clubhouse has an ambient atmosphere where residents and renters gather twice weekly to enjoy appetizers, drinks, and stimulating conversation, something truly unique in any Longboat Key community.brbrbrbr#516 on the 1st floor offers comfortable furnishings with a modern beach flair. This unit offers a private patio with a beach view to soak in the Florida sunshine. Amenities include a full-size kitchen with a microwave dishwasher, 12 cup standard coffee maker, full-size washer & dryer, a 46 TV in the living room, and 1 parking spot. Reserve your accommodations for the perfect island vacation!brbrbrbrAccommodations: 2-Bedroom, 2-Bathrooms plus Den/Office with Trundle BedbrbrbrbrBedding: 1 King, 1 Full, 1 Trundle BedbrbrbrbrAmenities and Club Facilities Include: Longboat Key's finest 8 Har-Tru tennis courts (some lighted for night play), 2 heated community swimming pools, sauna/whirlpool/locker rooms, clubhouse, exercise facility, community propane grill, library, onsite management, tennis professional, beach access, fishing, and bocce ball.brbrbrLocation: 5055 Gulf of Mexico Drive #516, Longboat KeybrbrbrbrView: Beach view but view is obstructed by sea grapes - private patio faces the GulfbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $100 Rental Application Fee

2

Bed

2

Bath

6

Sleeps

$379.00

/ Nightly

Apartment / Condo

Beachplace on the Beach 2 Bedroom hosted by FGC

1115 Gulf Of Mexico Drive #204

Beautiful fully remodeled condo in Beachplace. Raised ceilings, tile floors, upgraded kitchen including a wine fridge, upgraded finishes throughout. This unit books quickly so contact us today for your vacation home in paradise. The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs and umbrellas included • Wi-Fi • Lighted tennis courts • Heated pool and hot tub • Two state of the art fitness centers • Air conditioned clubhouse • BBQ gas grills by the pool. Property has a 1 month minimum requirement. We have over 20 listings at Beachplace. Please Call us.

Bed

Bath

Sleeps

$365.09

/ Nightly

Condo

Ground-Floor Gulf Retreat-Outrigger #5 by RVA

Longboat Key, Florida, United States

RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger Resort. The Outrigger grounds offer coin-operated laundry facilities, BBQ areas, and direct beach access. This unit is perfect getaway with one-bedroom, one-bath and direct Gulf front view. Features TV's, stereo system, new furnishings, and tile floors throughout. Relax on your private screened lanai overlooking the beautiful Gulf of Mexico.brbrbrbrAccommodations: One-bedroom, one-bathroombrbrbrbrAmenities: Private Lanai, Grill, Full-size Kitchen, Wireless Internet, Community Pool, Washer/Dryer, On the Beach, Private Beach AccessbrbrbrbrLocation: 5155 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 1 Queen Sleeper SofabrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Restrictions: 7 Nights; Contact our local team for shorter stay options

1

Bed

1

Bath

4

Sleeps

$474.6

/ Nightly

Condo

2 Br/2Ba Gulf Front Condo w/ private beach access, on Long Boat Key, Florida

Longboat Key, Florida, United States

Discover the beauty of Longboat Key from this 2-bedroom condo. Beautiful, 2 Br/2Ba renovated Gulf Front Condo with gorgeous morning light and private beach available for rent on Long Boat Key, Florida. Steps to the pool and sand, kayaks, Hobie Cat, beach attendant with chairs and umbrellas to serve you. 2 tennis courts, pool, hot tub, bicycles, ping pong table and community room/workspace. The perfect place to vacation in March. Close to the new St. Regis and across the street from CVS, Publix grocery, nail salon, and restaurants. Enjoy nearby St. Armand's Circle, The Ringling Museum, The Mote Aquarium, as well as theaters and more shopping in Sarasota.

Bed

Bath

Sleeps

$252.04

/ Nightly

Condo

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Longboat Key, Florida, United States

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 #237 will have the option of temporary membership privileges, for a transfer fee, 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, fishing pier 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 #237 Features: Hotel Room in the Blue Gardens BuildingbrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 QueenbrbrbrbrResort 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

Bed

Bath

Sleeps

$312.81

/ Nightly

Condo

Beach Castle Bliss #22 by RVA

Longboat Key, Florida, United States

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature.brbrbrbrThe grounds here are impeccable – from the well-manicured vegetation to the vast palm trees that dot this serene Longboat Key location. The buildings at Beach Castle are the color of sunshine and are accented by Bahama shutters and railings that resemble palm trees. Each unit is individually owned, which means no unit is alike and provides a unique vacation experience to our guests. However, all units provide a full kitchen, living room and private lanais – never compromising the comforts of home.brbrbrbrThis secluded hideaway exudes a classic charm that, as vacationers, we yearn for. A place to get away from it all, relish in the Florida sunshine and reconnect with family and friends; all this while enjoying white-sand beaches, privacy and most importantly, vacation memories that last a lifetime. brbrbrbrLimited Membership Privileges: Guests of Beach Castle Resort #22 will have the option of 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, fishing pier and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Beach Castle Resort is a quiet, 21-unit condominium resort midway on the exclusive island of Longboat Key with a variety of views including Gulf front, Bay front, pool and garden views.brbrbrbrUnit #22 Features: Two-bedroom, two-bathroom unit with partial bay views and cathedral, tray ceilings. Decorated in modern, beach-style décor some additional upgrades you'll enjoy at Unit #22 include large, flat screen TV's and ceiling fans in the living room and bedrooms, custom tile flooring throughout. The kitchen of Unit #22 has been renovated to include new cabinetry, stainless steel appliances and granite countertops. brbrbrbrView: Partial-Bay ViewbrbrbrbrBedding: 1 King, 1 Queen, 1 fullbrbrbrbrParking: All guests have use of 1 assigned parking spot during their stay. Additional spots are available at a nearby community on a first-come, first-served basis. We kindly ask guests to plan accordingly.brbrbrbrPets: Pets are not permitted on Beach Castle property.brbrbrbrResort Features: Full-size Kitchen, Spacious Floorplans, Heated Community Pool, Community Hot Tub, Grills, On-site Office, Private Lanais, Complimentary Laundry Facilities, Shared Boat Docks (available on a first-come, first-served basis, a 26' boat limit, and guest is responsible to find off-site parking for boat trailer), Cable TV, Wireless Internet, Complimentary Guest Parking, Private Beach Access, Complimentary Lounge Chairs and UmbrellasbrbrbrbrPlease Note: Beach Castle is a self service resort; we do not provide daily housekeeping services. For your convenience, an amenity “Starter Kit” is provided to assist you upon your arrival. Any essentials required after the initial provided, such as toilet paper, dish soap, etc. is the responsibility of the guest.

2

Bed

2

Bath

6

Sleeps

Select Dates for Price

Private Vacation Home

Upscale Canal Home – Private Pool & Boat Dock: Hideaway Bay in LBK by RVA

Longboat Key, Florida, United States

Escape to paradise at Hideaway Bay, a luxurious 4-bedroom, 5-bathroom canal-front home nestled in the exclusive Longboat Key community. Thoughtfully managed by RVA, this elegant getaway sleeps up to 8 guests and offers the perfect blend of coastal charm and upscale comfort.brbrSituated directly on a serene canal, Hideaway Bay features a private dock—ideal for boating enthusiasts, kayakers, or simply relaxing waterside with your morning coffee. Whether you're arriving by boat or planning to rent one locally, the easy water access adds a unique touch to your Gulf Coast vacation.brbrStep inside to a spacious, light-filled interior with open-concept living areas, coastal-inspired décor, and panoramic views of the water. The gourmet kitchen is fully equipped for entertaining, while multiple indoor and outdoor lounging areas make it easy to unwind in style.brbrEach of the four bedrooms is a private oasis with en-suite bathrooms, offering comfort and privacy for families or groups. The expansive primary suite includes a spa-like bathroom and private balcony views overlooking the pool and canal.brbrAdditional highlights include:brbr5 full bathrooms for ultimate conveniencebrbrPrivate dock with direct canal accessbrbrOutdoor dining and lounge areasbrbrWasher/dryer and Wi-FibrbrJust minutes from beaches, dining, and golfbrbrWhether you’re here to fish from the dock, explore nearby Sarasota, or soak up the Florida sun, Hideaway Bay is the perfect home base for your Longboat Key adventure.brbrBook your stay at Hideaway Bay today and experience coastal living at its finest.brbrMinimum restrictions applybrApplication + Application fee required, application may have a 30 day turnaround.

Bed

Bath

Sleeps

$310.56

/ Nightly

Private Vacation Home

Cedars East Getaway–Tennis & Gulf Breezes 507/RVA

Longboat Key, Florida, United States

Recently Renovated Luxury Condo at Cedars East – Prime Longboat Key LocationbrbrWelcome to Cedars 507, a beautifully newly renovated Longboat Key vacation rental that has been completely updated from top to bottom by its new owners. This exceptional condo features an open, airy floor plan, soaring ceilings, abundant natural light, and stylish coastal furnishings throughout. The modern kitchen boasts stainless steel appliances, quartz countertops, and is fully equipped for both short-term and extended stays.brbrbrUnbeatable Mid-Island Location: Perfectly situated in the heart of Longboat Key, Cedars 507 offers easy access to the best of the area. You’re just minutes from the boutiques and dining of St. Armands Circle and Anna Maria Island’s Bridge Street, with several excellent restaurants within walking and biking distance—including Hugo’s, conveniently located onsite.brThe condo is:br• A 5-minute walk to Sarasota Bay, featuring a fishing pier and a peaceful secondary bay beach (accessible during low tide)br• Steps from the island-wide walking and biking trail, offering scenic access from end to end of Longboat KeybrbrbrResort-Style Amenities at The Cedars Club: Guests enjoy full access to The Cedars Club, one of the premier private clubs on Longboat Key, located just a 2-minute walk from the unit. Amenities include:br• A junior Olympic-size swimming pool with ample loungers and umbrellasbr• A 24-hour state-of-the-art fitness centerbr• Nine Har-Tru tennis courts and three Har-Tru pickleball courts (easier on the joints than hard courts)br• Onsite tennis pro available for lessonsbr• Complimentary bicycles for guest usebrbrbrEasy Access to Pristine Longboat Key Beach: Cedars 507 is located directly across the street from beautiful Longboat Key Beach. The owners provide everything you need for a perfect beach day, including:br• Tommy Bahama beach chairs (replaced annually)br• Beach umbrellas with sand anchorsbr• A convenient beach wagonbrbrbrProfessionally Managed with 24-Hour Support: This property is professionally managed by RVA Resort Vacations, the premier onsite management company on Longboat Key. Guests enjoy 24-hour support and maintenance, ensuring peace of mind throughout your stay—no need to track down an owner if anything arises.brbrbrPrivate Views and Relaxing Outdoor Space: The rear of the condo overlooks a lush mangrove preserve, offering exceptional privacy from the master bedroom and the spacious screened-in lanai. The kitchen and second bedroom feature a partial ocean glimpse, adding to the coastal ambiance.brbrbrComfortably Appointed for Short or Long Stays: Cedars 507 is thoughtfully furnished and fully equipped, featuring:br• King bed in the primary suitebr• Queen bed in the guest bedroombr• Two and a half updated, modern bathroomsbr• Full-size washer and dryerbr• Three flat-screen TVs with cable, DVD player, and Hulubr• High-speed wireless internetbrbrbrWhy Guests Love Cedars 507: The owners of Cedars 507 were longtime renters on Longboat Key and thoughtfully designed this home to include everything they valued most in a vacation rental. The result is a standout condo offering comfort, location, amenities, and style—ideal for a truly memorable Longboat Key beach vacation.brbrbrUnit Amenitiesbr• 1-Car Garagebr• Full-Size Kitchenbr• Wireless Internetbr• Private Screened Lanaibr• Fitness Facilitybr• Community Poolbr• Public Beach Access (Short Distance Away)brbrbrLocation: 507 Forest Way (Garden View)brBedding: 1 King | 1 QueenbrMinimum Night Requirements ApplybrNo Pets Allowed

2

Bed

2

Bath

4

Sleeps

34228, Florida, United States Vacation Rental Homes By Owner

$350.61

$233.6

$265.94

$222.26

$452.0

$474.6

$361.46

$299.54

$304.43

$438.01

$224.28

$379.00

$365.09

$474.6

$252.04

$312.81

$310.56

Rent a place that suits your needs

Most popular vacation rentals in Longboat Key

$747.69

$2112.85

$1196.70

$1148.84

$1024.99

$884.08

$861.14

$767.89

$755.36

$670.46

Most Popular Cities in Florida