Vacation Condo Rentals By Owner In Longboat Key, FL

Welcome to Bay Dream Believer, your elegant bayfront retreat on beautiful Longboat Key, Florida. This stunning 2-bedroom, 2-bathroom condo offers panoramic views of Sarasota Bay through massive floor-to-ceiling windows and an enclosed patio that lets you enjoy the scenery year-round. With public beach access just across the street, you’ll experience the best of both worlds — tranquil bayfront living and easy access to the Gulf sands.brbrStep inside to discover a tastefully upgraded interior featuring modern finishes, coastal-inspired décor, and an open layout filled with natural light. The fully equipped kitchen has everything you need to prepare meals at home, while the spacious living and dining areas are perfect for relaxing or entertaining. Both bedrooms are designed for comfort, with the primary suite showcasing incredible bay views and a peaceful ambiance.brbrThe community offers resort-style amenities including two heated swimming pools, convenient elevator access, a fitness center, community kayaks, tennis and pickleball courts, and scenic walking paths along the bay. Reserved parking adds convenience, and pets are welcome upon approval so you can bring your four-legged family member along.brbrWhether you’re here for a short getaway or an extended stay, Bay Dream Believer delivers the perfect mix of comfort, luxury, and coastal charm. Enjoy easy access to St. Armands Circle, Lido Key, and Anna Maria Island, where you’ll find endless shopping, dining, and entertainment options — all just minutes away.brbrBook your stay at Bay Dream Believer and experience why Longboat Key is one of Florida’s most peaceful and picturesque coastal destinations.brbr15 DAY MINIMUM BOOKING PRIOR TO CHECK IN! Association application requires social security numbers.

Luxury Bayfront Condo | Stunning Views, Pools & Beach Across Street

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$345.56

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.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 #241 Features: 1-bedroom, 1-bathroom unit in the Green Building with a direct pool view and a distant Gulf view from your private patio.brbrbrbrView: Pool/Gulf ViewbrbrbrbrBedding: 1 King + Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Relax, Recharge & Repeat – Silver Sands #241 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$484.25

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 #1 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 #1 Features: Two-bedroom, two-bathroom first-floor unit located on the Gulf side. Decorated in pastels, Florida charm with updated amenities including wireless Internet, granite countertops, updated appliances, and LCD, flat-screen TV’s. Netflix available.brbrbrbrView: Gulf Front ViewsbrbrbrbrBedding: 1 King, 2 Queens, Sleeper SofabrbrbrbrParking: 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.

Beachfront Bliss: Beach Castle #1 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$287.68

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 #235 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #235 Features: 2-bedroom, 2-bathroom unit in the Blue Gardens BuildingbrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, 2 Twins, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Gulfside Getaway – Silver Sands Resort #235 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$332.24

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. Relax by the heated community pool, take a stroll along the romantic beaches, or enjoy a short drive to the world famous St. Armand's Circle. This one-bedroom, one-bath Gulf front unit offers beautiful decor and views. Relax on your private screened lanai and escape to paradise.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 KingbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Restrictions: 7 Nights; Contact our local team for shorter stay options

Outrigger #8 Condo by RVA Peaceful Gulf

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$412.95

RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambiance and relaxed atmosphere of this vacation hideaway, coupled with the natural foliage and perfect location have created a must-see community on Longboat Key. The attention to detail, from the cleanliness of your unit to the manicured grounds, will be evident the moment you arrive. The glorious sunrises, the romantic sunsets, the lush tropical flowers abloom everywhere - you will believe you have found a personal paradise in the Cabana Beach Club. Many of our guests return year-after-year to relax and enjoy the area’s many attractions. Resort amenities include a heated swimming pool, community laundry facilities and complimentary chaise lounges.brbrbrbrAccommodations: Cabana Beach Club is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key with several units also located on the bay side. Choose from our various unit styles including one-, two-bedroom and efficiency units. Enjoy all the amenities of home in these fully furnished condominiums including TVs, full-sized kitchen or kitchenette, dining room, and modern, beach-styled decorations.brbrbrbrResort Features: Heated Swimming Pool, Private Beach Access, Internet Access (select units), Complimentary Chaise Lounge Chairs, Fully Equipped Kitchens or Kitchenettes, Barbeque Area, Private Patio or Lanai, Community Laundry Facilities, Outdoor Shower, Various ViewsbrbrbrbrUnit #7 Features: This two-bedroom plus den, two-bath unit is the largest at Cabana Beach Club and will easily accommodate 6 guests. Recent renovations include a beautiful new full-sized kitchen with granite countertops, all new stainless steel appliances, a full-sized washer and dryer in the unit, updated bathroom, and wireless Internet access. The outdoor lanai overlooking the pool is the perfect spot for morning coffee. Best of all, the beach is only steps away! Don’t wait, your perfect vacation is just a click away.brbrbrbrView: Gulf Front ViewbrbrbrbrBedding: 2 Kings, 1 day Bed/trundle

2BR Gulf View Condo Cabana Beach Club #7 by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$288.15

Escape to this brilliant condo in picturesque Longboat Key. This cozy retreat features 2 bedrooms with a king bed and full bathroom, and twin beds with full bathroom, perfect for a small group of guests. Enjoy the serene atmosphere and modern amenities like a fitness room , BBQ area, heated swimming pools. One over looking our lanai and Sarasota Bay. Or if prefer , you can walk across the street to our deeded private gulf beach. No trucks allowed. Our place will help you feel at home while enjoying your stay

Charming 2-bedroom condo overlooking Sarasota Bay on Longboat Key

Longboat Key, Florida, United States

Bed

Bath

4

Sleeps

$351.37

Welcome to your Longboat Key getaway at Buttonwood Cove 103C, a beautifully renovated 2-bedroom, 2-bath condo where comfort, style, and island charm come together. Perfectly positioned in one of Longboat Key’s most desirable communities, this inviting retreat offers stunning views of Sarasota Bay along with private beach access just across Gulf of Mexico Drive.brbrInside, you’ll find a fresh, recently renovated interior with tasteful finishes, comfortable furnishings, and an open layout designed for easy coastal living. The spacious living area flows seamlessly to the screened lanai, where you can enjoy morning coffee, evening cocktails, or simply relax while taking in the peaceful bay views and warm Florida breezes.brbrBoth bedrooms are thoughtfully furnished with king beds, making this condo an ideal retreat for couples, friends, or seasonal guests seeking both comfort and privacy. The primary suite features an en-suite bath, while the guest bedroom and second full bath offer a welcoming setup for additional guests.brbrButtonwood Cove is known for its beautifully maintained grounds and outstanding amenities, including a waterfront heated pool, tennis courts, fishing pier, kayak launch, clubhouse, and deeded private beach access directly across the street on the Gulf side. Spend your days enjoying the best of both worlds, sunrise views over the bay and sunset walks on the beach.brbrLocated on the peaceful north end of Longboat Key, you’ll be just minutes from local dining, shopping, and the boutiques and restaurants of St. Armands Circle.brbrWhether you’re planning a winter retreat or an extended island escape, this Buttonwood Cove condo offers the perfect combination of updated style, resort-style amenities, bayfront serenity, and private beach access. brbrProfessionally managed by Florida Vacation Connection.

Renovated 2BR/2BA condo - Buttonwood Cove 103C by FVC

Longboat Key, Florida, United States

Bed

Bath

4

Sleeps

$174.13

Welcome to your perfect Gulf Coast getaway! This stunning 2-bedroom, 2-bathroom condo offers breathtaking, direct views of the Gulf of Mexico, right from your own private balcony. Located in the highly sought-after Seaplace community, you’ll enjoy a peaceful, gated environment with resort-style amenities.brbrFeatures & Amenities:brbrSpectacular Gulf Views br2 Spacious Bedrooms with comfortable, modern furnishingsbr2 Full Bathrooms with updated fixtures and plenty of spacebrFully Equipped Kitchen perfect for preparing meals or entertainingbrPrivate Balcony to enjoy the sunset, ocean breeze, and panoramic viewsbr2 Heated Pools & 2 Hot Tubs for relaxing after a day at the beachbrDirect Beach Access just steps away from the condobrLocated Next to the Newly Built St. Regis Hotel, offering extra dining and entertainment options nearbybrbrWhether you're relaxing on the beach, lounging by the pool, or enjoying the local area, this condo is the ultimate spot to unwind. With top-tier amenities and a prime location, it’s the perfect retreat for families, couples, or friends.brbrBook your stay today and experience the best of coastal living!

Gulf of Mexico Direct Gulf View Condo

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$262.69

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!brbrbrbrLimited Membership Privileges: Guests of Silver Sands #232 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #232 Features: 1-bedroom, 1-bathroom unit adjacent to the office brbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Relax at Gulf – Silver Sands Resort #232, Longboat

Longboat Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$357.29

Enjoy elevated views that span the harbourside greens from the comfort of the 3BD/2BA villa residence positioned behind the private gates of Bay Isles on Longboat Key. Spacious upon entry, you are met with a foyer that opens to a combined living and dining area which further leads into a family room and kitchen space. These, along with the master bedroom, are positioned to front the golf course and offer terrace access; a place for a perfect afternoon of warm relaxation within an expanse of pleasing greenery. The location of this unit is ideal for receiving the peaceful and quiet vacation you deserve; while still in close reach of attractions and activities of cultural downtown Sarasota. brbrbrWake up in the morning to the sounds of birds chirping and plan a full day of visiting St. Armands Circle, enjoying a pleasant bike ride around the island, taking a dip in the sparkling community pool, feeling the warmth of the Gulf of Mexico, or venturing to downtown Sarasota. The Longboat Key lifestyle is one of a kind and it is waiting for you.brbrbrbrOther details of this residence include beach access thru the Bay Isles Beach Club where you can have a picnic and grill, partake in a volleyball game, and shower off before heading home. brbrbrbrAccommodations: Three-bedroom, two-bathbrbrbrbrAmenities: Private Balcony, Beach Access, Full-size Kitchen, Community Pool, Community Hot Tub, Tennis Courts at Bayfront Park, Wireless Internet Access, Washer/DryerbrbrbrbrLocation: 2115 Harbourside Dr., Longboat KeybrbrbrbrBedding: 2 King, 1 QueenbrbrbrbrView: Golf Course ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $100 Fee + Application + 30-Day Approval Time

Harbour Hideout: Condo on Longboat Key by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$302.57

Discover a newly renovated beachfront sanctuary where Tommy Bahama-inspired style meets modern luxury. This 4th-floor retreat features travertine marble floors, granite countertops, and custom cabinetry throughout. Relax on your private lanai as the sun sets over the Gulf of America, or spend your days enjoying our heated beachside pool, private tennis and pickleball courts, and exclusive beach access.brAdventure awaits with bay access for kayaking and fishing, and Bayfront Park just across the street. When you aren't exploring, unwind in the spacious living area featuring smart TVs, a new Bassett sectional, or retreat to the master suite with its own private balcony and spa-like walk-in shower. Located just seven minutes from the world-class dining of St. Armand's Circle and the cultural gems of Sarasota, this is the ultimate tropical lifestyle.

Exquisite Beachfront Condo with both Sunrise & Sunset Views

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$338.93

MONTHLY/SEASONAL RENTAL! Welcome to Paradise. This very comfortable and spacious 3rd floor, 1500 sqft 2 bed/2 bath condo has 3 different water views. Master bedroom has King size bed & second bedroom has twin beds. The casual beach condo sleeps 6, and features a fold out sectional sofa, washer/dryer, granite counters, and 2 enclosed lanais. Amenities include basic cable, WiFi, heated pool, canoe/kayak launch, fishing pier, tennis/pickleball court, outdoor grills, updated club room with kitchen. Portobello is a friendly condo complex, close to everything, with access to the bay and its own private beach. This is a place you will love to return to every year. (Please note strict occupancy limit of 6 people. Condo board fines $500 per day for occupancy over 6 people. An HOA information form must be submitted and approved prior to tenancy.)

Beautiful Portobello Condo Steps to Private Beach, Tennis and Pool

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$153.53

Seasonal And Monthly Rental. Beautifully remodeled 1st floor Whitney Beach condo where you can enjoy the easy carefree island living here in this newly remodeled beach condo. The highly desirable ground floor condos here at Whitney Beach provide an additional 200sf+/- of outdoor space in the form of two separate outdoor patios. The front courtyard with privacy fencing and pavers is perfect for outdoor living and toy (Kayaks, Sup, Bikes, Beach gear) storage. The very scenic back paver patio provides a tranquil space to take in the sights and sounds of island life as an ideal dining space. As you make your way inside you will immediately notice improvements and upgrades. brbrThe interior offers a large open space that really leads the 1-bedroom condos in spaciousness here on Longboat Key. The beautifully remodeled kitchen opens up and overlooks the large living and dining areas that provides a wall of glass overlooking a scenic back patio with lush tropical landscape that is legendary here at Whitney Beach plus peek-a-boo view of Bishops Bayou. Upgrades include Kitchen remodel with new stainless steel appliances, new faucet, new sink, beautiful quartz countertop and stylish backsplash. Living room is filled with very attractive new flooring and modern furniture. The Master bath is a spa like atmosphere. It has been completely remodeled with a walk-in shower, floor to ceiling modern tile, glass doors, new flooring and very attractive dual vanity with vessel sinks. Master bedroom en-suite provides direct access from the bathroom to the oversized master bedroom with a spacious closet. The complete interior is freshly painted with a cool coastal contemporary feel. In-unit washer / dryer plus outside storage providing tremendous convenience. brbrThis condo community as a whole has never been better! Three years of improvements in this timelessly favored complex with new and improved boat docks, decking and boat house. Buildings have been repainted and all courtyard fences, stairways and walkways have been replaced. New landscaping, paver walkways and lighting fixtures throughout. Whitney Beach is a Beach-to-Bay community providing access to Bishop's Bayou leading to Sarasota Bay for boating, kayaking and paddle boarding. On the beach side, there is Whitney Beach Conservatory, land owned by the condo association for use by residents and guests with 800 ft of pristine beach frontage on the Gulf! There are 2 tennis courts, 2 tiki huts and picnic areas, two heated swimming pools, Bbq area and the beautiful beach with lounge chairs for use on the gorgeous white sand of Longboat Key. brbrThis is a destination you will enjoy on the beautiful north end of Longboat Key! Plenty of restaurants and shopping are close by in the Whitney Beach Plaza and the historic Village district. Short drive to Anna Maria and St. Armand's Circle, featuring world-reknown shopping and dining.brbrRates shown are base rents that include utilities. Additional fees include departure cleaning fees, Internet fees if not provided by Owner, sales/resort taxes and pet fees if applicable. Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received. Holiday rates may apply as applicable.brbrAmenities Include:brbr- View: Garden Viewbrbr- Application Fee Req.: Yesbrbr- Waterfront: Bayside communitybrbr- Beach Distance: Closebrbr- Pool, Heated: Heated Poolbrbr- Beach Access: Deededbrbr- Pool: 3 Community Poolsbrbr- TV Cable/Satellite: Cable TVbrbr- Internet Access: Wifibrbr- washer dryer: washer dryer in Unitbrbr- Bed Size 1st/Master: Kingbrbr- Beds Pull-out: Sleeper sofabrbr- Floor No.: Ground Floorbrbr- Parking: One Reserved Parkingbrbr- Patio: Enclosed openbrbr- Furnished: Turnkey Furnishedbrbr- Master Bath Features: Walk-in showerbrbr- Community Features: Pool-tennisbrbr- Tennis: Tennis Courtsbrbr- Minimum Stay: 30 daysbrbr- Agent: Gregory Kossbrbr- Office: Longboat Keybrbr

Longboat Key Paradise! Pool ~ Beach ~ Kayaking ~ Shopping

Longboat Key, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charming wooden boardwalk that extends to the back of the property. Hugged by lush landscaping and featuring a spectacular swimming pool, Sea Twig is a paradise beach getaway. This two-bedroom, two-bath unit is beautifully furnished in Florida pastel decorations. Enjoy the hardwood floors, full-sized kitchen, private lanai, and community pool.brbrbrbrAccommodations: Two-bedroom, two-bathbrbrbrbrAmenities: Private Lanai, Grill, Wireless Internet, Full-size Kitchen, Community Pool, Washer/Dryer, Beach AccessbrbrbrbrLocation: 5645 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 King, 2 TwinsbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Requirements: Restrictions Apply

Gulfside Escape at Sea Twig #103- Relax & Unwind Steps to Sand & Pool by RVA

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$598.57

Unit #221S - Spacious & Upgraded 3-Bedroom Beachfront Condo on Longboat KeybrbrExperience the perfect blend of comfort and convenience in Unit #221S, a beautifully upgraded three-bedroom condo on Longboat Key. This unit is the result of combining #220 and #221 through a lock-off door, creating a spacious retreat ideal for families or larger groups.brbrRecently renovated with stylish, modern furnishings, Unit #221S offers a full-sized dining room and a well-equipped kitchen, perfect for preparing meals at home. There's also a kitchenette for added convenience, plus a private balcony off the kitchen where you can enjoy your morning coffee or evening cocktails while soaking in the fresh air.brbrWith two king-sized beds and one queen-sized bed, the condo comfortably accommodates up to 8 guests. Relax in the cozy living area, or take advantage of the beach access just steps away. With three bathrooms, each with a hairdryer, this condo is designed for comfort and practicality.brbrAdditional amenities include WiFi, heating, air conditioning, and a washing machine for your convenience. Whether you're lounging by the pool, exploring the local area, or unwinding on the beach, Unit #221S is the perfect home base for your Longboat Key vacation.brbrBook your stay today and enjoy all this beautiful condo has to offer!

3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.

Longboat Key, Florida, United States

3

Bed

3

Bath

8

Sleeps

$288.15

Stay comfortably in Longboat Key at this lovely 2-bedroom condo. The space features a king bed and twin beds, plus a cozy living room with queen sofa bed for extra guests. With two bathrooms, each equipped with a shower and hair dryer, getting ready is a breeze. The condo offers a tranquil atmosphere, perfect for unwinding after a day of exploring. Guests can enjoy the convenience of heating and air conditioning to stay comfortable year-round. Kick back, relax, and enjoy everything Longboat Key and our tremendous condo has to offer.

Cozy 2-bedroom condo in fantastic Longboat Key, Florida

Longboat Key, Florida, United States

Bed

Bath

6

Sleeps

$223.26

Luxury Waterfront Retreat at Grand Bay – Unit 626, Longboat Key brbrExperience the ultimate in coastal elegance at this stunning waterfront condominium at Grand Bay on Longboat Key. Professionally managed by Florida Vacation Connection, this beautifully appointed two-bedroom, two-bathroom residence offers breathtaking bay and golf course views, resort-style amenities, and a prime location near St. Armands Circle and downtown Sarasota. brbrStep into a bright and spacious open-concept living area, where floor-to-ceiling windows showcase the sparkling waters of Sarasota Bay. The expansive terrace provides the perfect spot for morning coffee or evening cocktails as you take in the serene surroundings. brbrThe fully equipped gourmet kitchen boasts granite countertops, modern appliances, and ample space for preparing meals. The elegant primary suite features a king-size bed, terrace access, a spa-like en-suite bathroom, and walk-in closets. The guest bedroom is thoughtfully designed with comfort in mind, making it a welcoming retreat for visitors. brbrAs part of the exclusive Grand Bay community, guests will enjoy access to a wealth of resort-style amenities, including: br- A heated waterfront pool and spa br- A state-of-the-art fitness center br- Tennis courts for friendly matches br- A private beach club for residents and guests br- 24-hour gated security for peace of mind brbrLocated just minutes from white sandy beaches, world-class dining, and upscale shopping, this luxury retreat is the perfect escape for those seeking relaxation, adventure, and everything in between. brbrBook your unforgettable Longboat Key getaway today!brbrTown of LBK RRR-01259.2025

Grand Bay 626 by FVC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$396.93

Escape to a tranquil paradise on Longboat Key and discover the hidden gem known as Pura Vida, a delightful 2-bedroom, 2-bath ground floor condo located within the serene Beach Castle Resort in unit 15. With its beautifully updated interior boasting a cool and clean coastal chic aesthetic in soothing hues of blue, cream and white, this vacation rental promises a relaxing retreat like no other.brbrThe primary suite is a haven of comfort and style, featuring a spacious bathroom with a walk-in shower, a single sink vanity, and all the amenities you need. Sink into the plush platform king bed with solid wood nightstands and a generous dresser while enjoying your favorite shows on the flat-screen TV.brbrIn the guest bedroom, you'll find two inviting queen beds, adorned with crisp white bedding, and a charming, distressed-washed dresser. A flat-screen TV is also at your disposal for entertainment. Rest and rejuvenate in this peaceful space.brbrThe open living and dining area is designed for relaxation and socializing. Unwind on the comfortable cream colored sofa or ultra-suede swivel chairs while watching movies on the large flat-screen TV. Gather around the modern dining table for four, where you can enjoy meals and create lasting memories.brbrThe well-appointed kitchen is equipped with modern stainless-steel appliances, a granite countertop, and an abundance of glasses, cookware, and utensils. Whether you're a culinary enthusiast or just need to prepare a quick snack, you'll find everything you need here.brbrThe guest bathroom is equally impressive, featuring a granite vanity, sink, and a spacious walk-in shower. Convenience and elegance seamlessly combine in this space.brbrStep outside from the living room onto the screened-in lanai, where you can savor your morning coffee or dine al fresco at the outdoor table and chairs. Surrounded by tropical landscaping adorned with mature mango trees and swaying palms, this private retreat offers a serene space to unwind and soak up the natural beauty.brbrFor those seeking aquatic adventures, the condo is just a few steps away from the heated community pool and hot tub. Sun loungers, umbrellas, tables, and chairs are at your disposal, ensuring you can bask in the Florida sun in style and comfort.brbrBeach lovers will be delighted to know that the resort provides private access to the pristine Gulf of Mexico beaches, offering endless opportunities for sunbathing, swimming, and beach combing. Additionally, water enthusiasts can take advantage of the private boat dock on the bay, perfect for fishing, kayaking, or boating.brWhether you're seeking relaxation, outdoor adventures, or a peaceful getaway, Pura Vida at Beach Castle Resort on Longboat Key offers it all. Book your vacation rental today and experience the beauty and serenity of this secluded paradise. Your perfect vacation awaits!brbrAbout Beach Castle ResortbrEscape to the timeless allure of Beach Castle Resort, a family-friendly community nestled on picturesque Longboat Key, offering an enchanting blend of Old Florida charm and modern comfort. The resort boasts a range of accommodation options, including 1 and 2 bedroom condos, each meticulously designed to provide a cozy and inviting atmosphere for your stay.brbrImmerse yourself in the essence of relaxation at our community heated pool and hot tub, surrounded by comfortable chairs, umbrellas, and tables, perfect for unwinding under the warm Florida sun.brbrIf you're a fishing enthusiast, our private boat dock with a convenient fishing table awaits your catch of the day. Savor the outdoors with a bayside gas grill, ideal for cookouts, and enjoy your meals at the adjacent table and chairs.brbrExploration is at your doorstep, with a leisurely stroll to nearby restaurants and shops. And when you're ready for some beachfront bliss, our private beach access welcomes you with sun loungers, umbrellas, and a beachside patio featuring a table, chairs, and a gas grill for seaside picnics. Rinse off the salt and sand in our outdoor shower after a day in the waves.brbrAt Beach Castle Resort, you have the flexibility to enjoy a short getaway or an extended stay, making it one of the rare resorts that cater to your vacation preferences. Discover a tranquil haven where memories are made and cherished amidst the beauty of Longboat Key's coastline.brbrLongboat Key Life brLongboat Key is a quieter gulf-side retreat located between Lido Key and Anna Maria Island along Florida's southwest coast. The barrier island is surrounded by the beautiful Gulf of Mexico and Sarasota Bay. The island's eastern shoreline is covered in mangroves with hidden canals and marinas. On the western shoreline, you can walk for miles on the white sandy beaches and swim in the gentle gulf. Imagine spending your days beachcombing, snorkeling, kayaking, paddle boarding, fishing, sailing, golfing, or cycling along the island's winding bike path.brbrLongboat Key is known for its abundance of dining options. With the Gulf and Sarasota Bay in its backyard, many restaurants focus on serving local, fresh seafood while visitors enjoy amazing waterfront views.brbrJust south and across the bridge is bustling St. Armand's Circle, a popular destination filled with boutiques, cafes, restaurants and tropical landscaped courtyards. Head north on Longboat Key, cross the Longboat Pass bridge, and find yourself on Bradenton Beach, Anna Maria Island and Holmes Beach. This area offers gorgeous, white sandy beaches, crystal clear water, fun waterfront bars, restaurants and a variety of shops.brbr**IMPORTANT PARKING INFORMATION**brBeach Castle Resort has a new parking pass policy in place. Each reservation includes one on-site parking pass, which must be clearly displayed on your dashboard whenever your vehicle is parked on the property. You’ll find the pass inside the condo—please retrieve it after check-in time. To avoid any issues, we kindly ask that you do not park at the resort before check-in or without the pass displayed. Unauthorized vehicles may be towed. An extra parking pass will be provided for The Cedars Condominiums just a short distance up the street. Thank you for your cooperation and understanding!brbrTown of Longboat Key: RRR-00690.2025

Beach Castle Resort, 1st Floor, Pool, Walk to Beach/Bay

Longboat Key, Florida, United States

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