34228, Florida, United States Vacation Rental Condos By Owner - Page 25

Showing 500 Of 507 Vacation Rentals

$318.65

Rare 3 Bedroom Condo/Villa with Beautiful Bay Views

Longboat Key, Florida, United States

Enjoy beautiful Bay views from this spacious three bedroom two bathroom one-story (no elevator) villa that comfortably sleeps six. Brand new enclosed lanai with outdoor patio and all new windows. Completely updated exterior and interior with designer furnishing and decor. Gourmet eat-in kitchen with beadboard cabinets and stainless steel appliances. Weber gas grill. Spacious living/dining room with with flat screen HD TV/DVR. Master suite with walk-in closet and new bath, guest room with double bed looks over bay, 3rd bedroom with wireless internet, desk, and trundle bed. Beautiful tile second bath with full bath/shower. Full size washer and dryer in unit. Walk out to manicured grounds and bay. Glass enclosed lanai steps from bay. Covered carport parking with guest parking. Pool, tennis courts, and fitness center are close by. Beach access across street with parking. Minimum Rental: One Month required. Preference to 3 month renters due to high demand

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$132.4

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2 Bd/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico

Longboat Key, Florida, United States

Available from May 1, 2026 - December 12, 2026. Beautiful corner unit condo with an abundance of windows located between Sarasota Bay and across the street from the deeded Gulf of Mexico beach. The gated community complex has every amenity imaginable - four pools, tennis court, shuffleboard, kayak launch, and golf putting range. Residents will have access to the gym, sauna, poker room, ping pong, billiards, art studio, and woodshop. One bedroom has a king-sized bed, the second, two twin-sized beds and a queen inflatable mattress is available.brbrThe patio overlooks the boat canal to Sarasota Bay where you can lay on the sofa and read a book or sit and drink your coffee. There are TVs in each room and cable and wireless Internet are included.brbrThe owner can be reached by e-mail or phone if you have any issues during your stay. Additionally, there is an on-site management company available during business hours on weekdays.brbrSix miles to the south of Longboat Harbor is the lovely St. Armand's Circle with nice outdoor restaurants, shops, and great people-watching. Five miles to the north are Bradenton and Anna Marie Island with golf cart and scooter rentals, as well as beach-style eateries.brbrThe condo is a 25-minute drive from Sarasota Airport and a 70-minute drive from Tampa Airport. Uber and Lyft serve both airports, as well. There is one covered parking spot for the condo unit and guest parking is available. brbrThree bicycles can be used with the unit, as well as 2 lounge beach chairs and 2 short beach chairs. Bike paths are available throughout Longboat Key.

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Exceptional(1)

$363.82

/ Nightly

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Luxury Condo located on Beachfront Property

Longboat Key, Florida, United States

. The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise.

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$340.83

/ Nightly

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Beautifully remodeled condo with lots of amenities!

Longboat Key, Florida, United States

Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the flooring to the kitchen and baths, the decor is neutral with pops of color, giving the home a coastal urban vibe. The primary bedroom offers a king bed, walk-in closet with built-ins, and a desk. The primary bath has dual sinks and shower. The guest bedroom boasts queen sleeping accommodations and a TV. new luxury vinyl flooring throughout and gorgeous kitchen with stainless appliances, stone counters and lovely wood cabinetry. Outside your door you will find a bonus deck with chaises for sunbathing. This popular, Tim Siebert designed Gulf-to Bay community features 27 lushly landscaped acres, 4 Har-Tru Tennis Courts, a Jr. Olympic pool, kayak launch, bocce ball and fitness room in the clubhouse, and a gorgeous beach, located just across Gulf of Mexico Drive. St. Armands Circle is a short drive away, just over the Ringling Causeway you will find the vibrant downtown Sarasota arts and culture, as well as the many unique shopping and dining venues. Leases less than 7 months subject to additional taxes and fees.brbrPlease be advised that this property is currently on the market for sale, guests will be given reasonable notice for any showings.brbrFor additional details on Sarasota rentals and Longboat Key rentals contact Stephanie Deshaies at or email brbr***Information contained herein deemed reliable but not guaranteed***brbrAmenities Include:brbr- Bldg. Complex Name: Bayport Beach & Tennbrbr- Type Unit: Lowrise Condobrbr- Unit Rating: Goldbrbr- Beach Access Type: Walkbrbr- Distance to Beach: .10 Milesbrbr- Floor/Bldg Height: 2 of 2brbr- Year Built: 1983brbr- Approx. Sq. Ft.: 1,370brbr- Exposure/View: E/Greenspacebrbr- Pool/Spa: Communitybrbr- washer dryer: Yesbrbr- Parking Type: 1 Carportbrbr- Lanai / Balcony: Openbrbr- Master Bedroom: Kingbrbr- Bathrooms-Master: Showerbrbr- Guest Bedroom: Queenbrbr- Bathrooms-Guest: Showerbrbr- Flooring: Vinylbrbr- TV/Dvd/ Stereo: 2/0brbr- Internet Access: Wifibrbr- Listing Advisor: Stephanie DeShaiesbrbr- Min. Rental # x perYr: 30 x 12brbr- Security Deposit: $1,500brbr- Reservation Fee: $170brbr- Damage Protection: $60brbr- Application Fee Req.: $150brbr- Departure Clean Fee: $200brbr- Taxes: 13%brbr- Utility Charges: Includedbrbr- Rate - Monthly: $8,500/$4,250brbr

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$565.0

/ Nightly

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Newly renovated 2 bedroom beachfront condo

Longboat Key, Florida, United States

Two full bedroom with bath- completely renovated beachfront condo on Longboat Key. Located on The Longboat Key resort and golf club. Less than 2 miles from St Armand Circle for shopping and dinner. Private beach access, pool and hot tub on property. A gym in the common area and great location for long walks. Covered parking available. Publix market within a mile for grocery shopping. Full kitchen with all amenities for cooking. Washer and Dryer in unit. Master bathroom with double vanities and walk in closet. Full guest bathroom. Both bedrooms have king beds. All linens and towel provided. Wrap around patio for views of the golf course and The Gulf of Mexico. Private building with concierge service. Televisions in bedrooms and high speed WiFi included.

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$305.4

/ Nightly

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2-bedroom condo in beautiful Longboat Key with fitness room, AC

Longboat Key, Florida, United States

This charming condo in Longboat Key is a fabulous choice for guests looking for a cozy retreat. With 2 bedrooms including a king bed and a twin bed, along with 2 bathrooms featuring a shower and bathtub, this gorgeous property has everything you need for a comfortable stay. Plus, there's an additional living room space with a sofa bed for extra relaxation. Kickback, relax, and enjoy everything Longboat Key and our condo has to offer.

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Exceptional(2)

$297.8

/ Nightly

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Cozy private beach condo

Longboat Key, Florida, United States

Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enjoy breakfast, lunch or dinner with the beautiful view of the Golf of Mexico right from your lanai. This lovely condo has 2 bedrooms 2 bath with small office and full equipped kitchen. The condo is located in a second floor accessible by stair and just a short walk to the complex 600 feet of white sand beach front, heated pool and bbq area.

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$340.89

/ Nightly

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Charming 2-bedroom condo steps from Beach, Library and Grocery on Longboat Key

Longboat Key, Florida, United States

Get ready to relax in this marvelous 2-bedroom condo in Longboat Key. This cozy retreat features 1 king bed and 2 queen beds, perfect for a small group of guests. With fully equipped home, gigabit WiFi, smart tvs, full sized washer & dryer, a small office with door that can close, and all the small appliances you could need for a comfortable stay.brbrWe're steps from the beach, where you can begin or end your days with peaceful sand walks. Also conviently located a short walk away from Publix, the Library and LBK's small park. brbrCome undwind in peace and quiet, with our on site pool, covered parking, and secluded 4 unit condo association.

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Exceptional(184)

$427.61

/ Nightly

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Unit #208 Sand Cay Beach Resort Pool View

Longboat Key, Florida, United States

Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. brBrand new beds were delivered in December 2022. There is a twin and a full size mattress bunkbed, with a trundle, in the 2nd bedroom and a king mattress in the master bedroom. Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will become part of our Sand Cay family, and we will look forward to your return year after year.brWhen planning a trip to the beautiful Gulf Coast Beaches, stay with us. All of our private beautiful condominiums feature full kitchens, living rooms, dining rooms and a balcony or patio to enjoy. We offer pool and garden, gulf and gulf front beach views. Our property features a heated pool, shuffleboard court, full tennis court and an immaculate private, white sandy beach.brExperience the ultimate beachfront boutique Florida paradise at our resort.

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Exceptional(11)

$553.66

/ Nightly

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LaPlaya 108B-Dream views of the Gulf.

Longboat Key, Florida, United States

Beachfront 2 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute of the sunset. The unit has a fully equipped kitchen, washer and dryer, and all linens and beach towels are provided. Welcome to our island-style living!brbrOur condo’s open floor plan is comfortably appointed to reflect the sand and sea view from the spacious living/dining area and kitchen, with a screened beachfront lanai and convenient first-floor bathroom. The second floor features the master bedroom with king bed and a balcony perfect for sunsets or dolphin watching, and full size beds in the guest bedroom.brbrListen to the waves or watch the exquisite sunsets from your private balcony off the master bedroom of this two-level townhouse. Relaxation starts here on the wrap-around sofa in the spacious tiled living area. Step directly out to the beach from the screened first floor lanai. Quaint, classic, elegant décor.

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Exceptional(22)

$520.83

/ Nightly

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Sea Grape Inn #4- Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.br** Need to stay less than the minimum required nights Please contact us. **brCheck our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex, with 8 beautiful condos located beachside, on the shores of the Gulf of Mexico, on Longboat Key. A perfect beach getaway!brbrBEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.brbrA first floor 2 bedroom 2 bath condo that offers a view of the pool and Gulf of Mexico from the living area and the screened lanai which includes teak furniture. The primary bedroom offers a king bed and the guest bedroom offers a queen bed which has proven to be perfect for two couples with two larger beds and each having a private full bath. brbrBoth baths have been upgraded with new vanities, tile and toilets. The kitchen has been upgraded to include granite counter tops, newer sink and appliances. Tiled throughout and boast a tropical theme with Tommy Bahama furnishings. With the many paintings, sculpture and artistic touches that the owners have collected from throughout the world, this condo is truly an art lovers delight at the beach!brbrThe Following *Required Fees are included in the total cost.br*Required $150 Departure Cleaning Fee. brbr*Required Conservation Fee of $10 per night will be charged due to Longboat Key Ordinances to protect Turtles.brbr*Required Damage/liability insurance fee $70 is mandatory and will cover any damages or missing items in the guest rental unit or property, as needed. This damage/liability enables The Sea Grape Inn to rent to guests without requiring a refundable damage deposit. brbr brCANCELLATION POLICY:br~Cancel 91 days or more prior to arrival date, guest will receive a full refund less a $250 admin fee.br br~Cancel 31-90 days prior to arrival receive full reservation credit for a future booking valid for 1 year (less any booking fees). Original reservation pricing is not guaranteed. Guest will be required to pay the difference if there is a price increase for new booking dates.br br~Cancel 30 days or less prior to arrival, No Refund Or Booking Credit will be provided.brSee house manual in rental

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$327.03

/ Nightly

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Beachplace 8-601 by FGC

Longboat Key, Florida, United States

Experience Coastal Elegance at Beachplace PenthousebrbrWelcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking panoramic views of the pristine beach, the shimmering Gulf of Mexico, and mesmerizing sunsets that paint the sky year-round.brbrStep onto the expansive wrap-around balcony and let the gentle sea breeze and stunning vistas captivate your senses. Floor-to-ceiling sliding glass doors seamlessly connect the balcony to both the living area and the primary bedroom, creating a harmonious blend of indoor and outdoor living.brbrInside, the residence has been meticulously updated with exquisite finishes that exude sophistication and style. Revel in the beauty of new impact windows and sliding glass doors, complemented by plank-style ceramic tile flooring that mimics the warmth of wood. The redesigned kitchen is a culinary masterpiece, featuring quartz countertops, a built-in pantry with pull-out drawers, a wine refrigerator, and a charming window over the sink offering city and gulf views.brbrThe primary suite is a sanctuary of comfort, complete with a walk-in shower with a sleek glass enclosure, and a vanity area for your convenience.brbrBeachplace is more than just a home; it's a lifestyle. Enjoy access to a Jr. Olympic-sized swimming pool with swim lanes, a splash pool, a hot tub, a state-of-the-art fitness center, a grilling area, tennis and pickleball courts, all within a secure 24-hour guard-gated community.brbrIndulge in the ultimate beachfront living experience at Beachplace Penthouse, where every day feels like a vacation.brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.

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Exceptional(3)

$193.48

/ Nightly

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Beachfront Condo

Longboat Key, Florida, United States

Steps to the heated pool and gorgeous beach - which runs for over ten miles! Run out barefoot to the beach, enjoy a swim or relax on the beach chairs. Enjoy amazing sunsets from the screened lanai, living room or bedroom. Bike on the 12 miles of bike lanes. Convenient restaurants and shops right across the street. A few minutes walk to Durante park and nature reserve. Five minute drive to Publix, fifteen to St Armand's Circle with dozens of restaurants and shops. Our home faces west toward the sunset. Two bedrooms, both with king beds, deluxe brand new Stearns and Foster bed and walk-in closet in the main bedroom. Both with private baths. New flooring throughout (only small rug by TV). High-speed internet and cable tv included. New 65 inch LG OLED C5 TV and LG sound bar. New washer and dryer. Two desk/work areas. Additional futon nook for extra guest. Quiet north end of the island. Reserved parking. In unit laundry. Close drive to Sarasota and Anna Maria Island. One month minimum rentals. No pets.

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Exceptional(4)

$474.98

/ Nightly

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Beautiful Beachplace - 1135 Gulf of Mexico Drive

Longboat Key, Florida, United States

Enjoy spectacular sunsets from this direct Gulf front, 2 bedroom, 2 bath well appointed property. Located on the 5th floor, this unit features a King bed master suite, and two twin beds in second bedroom, flat screen TV's, wireless internet and washer and dryer. This immaculate unit has everything you will need for a relaxing care-free beach vacation. Beachplace is a 31 acre, beautifully landscaped, gated community that includes 24 hr. security, a junior-sized Olympic pool, tennis courts, grilling areas, clubhouse, and fitness center. A walk through the lush landscaping on the grounds leads to an extensive (1450 lineal feet) private beach. Exciting varied restaurants, shopping, active lifestyle activities & sightseeing are nearby. It is less than 3 miles from eclectic St. Armand's Circle, and approximately 5 miles from vibrant downtown Sarasota. Mote aquarium, fishing, hiking, beach strolling and nature walks abound. If you simply want to relax, beach umbrellas and chairs are laid out daily for your relaxation. Simply enjoy! Please ask Gulf Coast Rental Homes in Sarasota for more details. AVAILABLE JUNE, AUGUST, SEPT, OCT AND DEC, 2025! 30 day minimum due to HOA regulations.

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$302.06

/ Nightly

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Gulf Views & Cozy Comfort w Large Lanai Tern's Nest #22 Condo by RVA

Longboat Key, Florida, United States

Escape to paradise in this stunning Longboat Key condo, where every day starts with incredible water views and ends with breathtaking Gulf sunsets. brbrbrThis two-bedroom, two-bathroom retreat features an open and airy layout with plenty of room to relax. Step onto the spacious 26-foot screened-in lanai, your front-row seat to the Gulf of Mexico's blue waters and powdery white sand beaches—a perfect spot for morning coffee or evening cocktails. The large master suite opens directly onto your private Gulf-front lanai, creating a serene space for watching magnificent sunsets.brbrbrbrLocated in the charming Longbeach Condominium community, this retreat spans 17 lush, tropical acres on the north end of Longboat Key, blending Old Florida charm with privacy and tranquility. Yet, you’re just a short drive from the shopping, dining, and excitement of St. Armands Circle and the mainland. With a heated pool, direct beach access, and BBQ area, you’ll find plenty to enjoy here. brbrbrbrBook your stay and experience the tranquil beauty and unbeatable charm of Longboat Key!brbrbrbrAccommodations: 2-Bedroom, 2-BathroombrbrbrbrAmenities: Gulf Views, Full-size Kitchen, Large Screened Patio, Wireless Internet, Washer/Dryer on-site, Walking Distance to the Beach, Community Pool, Community GrillbrbrbrbrLocation: 7165 Gulf of Mexico Drive Unit #22, Longboat Key FL 34228brbrbrbrBedding: 1 King, 2 Twin BedsbrbrbrbrView: Gulf ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements (non refundable)br$125 + Application to Longbeach Condo Association,br$25 Check made payable to Lighthouse Property Management

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Exceptional(10)

$531.37

/ Nightly

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Sea Grape Inn #5- Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbr** Need to stay less than the minimum required nights Please contact us **brCheck out our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex with 8 private condominiums located beachside, on the shores of the Gulf of Mexico, on Longboat Key. A perfect beach getaway!brbrBEACH VIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbrBeautifully remodeled and upgraded; condo 5 sits directly on the Gulf of Mexico Beach and benefits from its prime block location offering optimum views of the pool and the gulf.brbrThis fabulous 2nd floor 2 BD/2 BA condo has been exquisitely upgraded to the highest specification. A completely re-designed and updated kitchen, featuring new cabinetry, stainless steel appliances, beautiful quartz counters, new sink and faucet and increased open area with a breakfast bar for 4. The refreshed living room area has a flat screen TV, sofa bed and new furniture throughout. A private screened lanai off of the living area provides the most outstanding views of the pool, Gulf of Mexico, and stunning sunsets. The beautifully appointed primary suite offers a king bed, flat screen TV, and an improved private bathroom. The refreshed second bedroom suite has two twin beds, a flat screen TV and an improved private shower room. New tiled floors throughout the living areas, plenty of new storage, stylishly re-decorated to create a cozy and elegant home 'with a from home feel' at the beach.brbrThe Following *Required Fees are included in the total cost.br*Required $150 Departure Cleaning Fee. brbr*Required Conservation Fee of $10 per night will be charged due to Longboat Key Ordinances to protect Turtles.brbr*Required Damage/liability insurance fee $70 is mandatory and will cover any damages or missing items in the guest rental unit or property, as needed. This damage/liability enables The Sea Grape Inn to rent to guests without requiring a refundable damage deposit. brbrCANCELLATION POLICY:br~Cancel 91 days or more prior to arrival date, guest will receive a full refund less a $250 admin fee.br br~Cancel 31-90 days prior to arrival receive full reservation credit for a future booking valid for 1 year (less any booking fees). Original reservation pricing is not guaranteed. Guest will be required to pay the difference if there is a price increase for new booking dates.br br~Cancel 30 days or less prior to arrival, or a No-Show; No Refund Or Booking Credit will be provided.brSee house manual in rental

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Select Dates for Price

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Beachplace 4 - 304 by FGC

Longboat Key, Florida, United States

Beautiful beachview unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors. brbrThe online system will only book 12 months out, so please call us directly if you wish to book further in advance.brbrOn the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.brbrThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brRental includes Cable tv, Wifi, parking, water and electric.br1 Month minimum requiredbrbrRRR-00583.2023

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Exceptional(1)

$182.62

/ Nightly

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DIRECT Gulf Front view from the 4th floor condo at Tiffany Plaza

Longboat Key, Florida, United States

Looking to work remotely during the summer and fall Why not consider working right on the beach Direct Gulf Front Rental available for August through to November 2023 along with the month of March 2024. Gorgeously renovated custom condo, 2 bedrooms, 2 baths. The renovated kitchen is complete with marble countertops and a wine refrigerator! This beach retreat has everything you need to get away from it all. The master bedroom has king accommodations, closets.The guest room offers queen accommodations with a desk overlooking the Gulf of Mexico. In unit washer/dryer and high speed WI FI complete the picture. You will love sitting on the Lanai overlooking the turquoise waters of the Gulf for morning coffee or sunset cocktails. This stellar location is close to dining, shopping and cultural venues, either north or south! (Two minutes north of Publix). The community amenities include a lovely sheltered heated pool, BBQ grills, club room with ping pong table, lending library. One covered parking space included, and plenty of guest spaces. Bayfront Park is also just a short stroll south and has fitness classes, yoga, tennis and pickleball courts, basketball, playground and is a great place to watch the sunrise!

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Exceptional(11)

$346.08

/ Nightly

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Find Your Sunshine Sanctuary on Longboat Key

Longboat Key, Florida, United States

Welcome to your sunshine-soaked escape on Crane’s Bay—where every condo gives you room to breathe, stretch, and settle into full vacation mode. With spacious layouts of 1,600 sq. ft. or more, these two-bedroom, two-bath retreats are designed for families, friend groups, and anyone craving a little extra elbow room.brbrYour Home Base in ParadisebrMain Bedroom: King bed + private bath = your personal recharge zonebrSecond Bedroom: Two twins bedsbrLiving Room: Sleeper sofa for the extra tagalongsbrFully Equipped Kitchen: Full-size appliances, cookware, blender (hello, smoothies), toaster, teapot, and coffeepot—because vacation fuel mattersbrIn-Unit Washer/Dryer: Stackable, convenient, and ready for sandy swimsuitsbrbrResort Perks Worth Packing ForbrHeated Outdoor Pool + Whirlpool (Dawn to Dusk)brRelax, float, soak—repeat. Winter who brTennis & Pickleball CourtsbrPlay a friendly match or unleash your inner Serena—your call.brGear on DeckbrAsk at check-in about our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing poles.br(First come, first vacationed.)brbrLobby Fun ZonebrBooks, games, and videos for rainy days, quiet nights, or the kid who always needs “one more thing to do.”brPicnic + BBQ AreabrGrill up something delicious under the Florida sky.brbrGood-to-Know DetailsbrParking: No campers, motorhomes, or trailers. Call us for storage options.brSmoking: Allowed only on balconies and designated spots—not inside.brPets: We love them, but not here. No pets permitted.brMax Occupancy: Six guests total (yep, kids count).brHouse Rules: No parties, no pets, no smoking/vaping inside.brViews: Balcony views vary by unitbrbrAge Requirement: 21+ to rent and check in.brMaintenance: Things happen—our team works quickly to make it right.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM

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Exceptional(36)

$352.82

/ Nightly

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Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access

Longboat Key, Florida, United States

Looking for a winter glow-up Welcome to Longboat Key—where sandy beaches, soft breezes, and that “I could really get used to this” island vibe turn even the coldest months into sunshine season. Your home base: a spacious 1600+ sq. ft. 2BR condo perched right over Crane’s Bay with front-row seats to postcard-perfect views (and the occasional surprise manatee cameo).brbrInside, you’ll find all the comforts of home—only sunnier.brMain Bedroom: King bed + private bath with a jetted tub worthy of vacation-level bubble bathsbrGuest Room: Two twin beds (aka the cozy kid zone or bestie bunk room)brLiving Room: Sleeper sofa for extra guestsbrSecond Bathroom: Easy access for everyone—no vacation “line for the shower” chaosbrbrA Kitchen Built for Vacation ModebrFully equipped with full-size appliances, roomy countertops, a breakfast nook made for slow mornings, and all the essentials—dishes, pots, pans, toaster, coffee pot, and utensils.brPlus, in-unit washer + dryer to keep swimsuits fresh and sandy footprints in check.brbrResort Perks to Keep the Good Times RollingbrHeated Outdoor Pool & Whirlpool (Dawn to Dusk)brPerfect for cold-weather refugees and sunset soakers.brTennis & Pickleball CourtsbrServe up some friendly competition—or just look sporty, no judgment.brBeach + Gear AccessbrAsk at check-in for our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing equipment.br(First come, first sun-kissed.)brPicnic & BBQ AreabrGrill, chill, and dine under the Florida sky.brLobby EntertainmentbrBooks, games, and videos—because even paradise has cozy indoor days.brbrBefore You Book, A Few Helpful NotesbrbrParking: No campers, motorhomes, or trailers. (We’ve got storage options—call us.)brSmoking: Allowed only on balconies or designated areas. Not inside.brPets: We love them too, but this property is pet-free.brOccupancy: Max of 6 guests, kiddos included.brHouse Rules: No pets, no smoking/vaping inside, no parties.brViews: your view may vary.brAge Requirement: 21+ to rent and check in.brMaintenance: If anything pops up, our team is quick on the fix.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM

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Most popular vacation rentals in Longboat Key

Exceptional(36)

$884.08

/ Nightly

Private vacation home

Hidden Bay/Beach Paradise

Longboat Key, Florida, United States

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Exceptional(36)

$746.18

/ Nightly

Private vacation home

Canal Front Home - 8 min walk to beach. RRR-00953.2023

Longboat Key, Florida, United States

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Exceptional(36)

$747.69

/ Nightly

Private vacation home

Longboat Key home on the canal and a 5 minute walk to the beach

Longboat Key, Florida, United States

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Exceptional(36)

$755.36

/ Nightly

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LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach along the turquoise Gulf of Mexico.

Longboat Key, Florida, United States

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Exceptional(36)

$767.89

/ Nightly

Condo

Beachfront 4th floor 4BR Longboat Key Condo With Stunning Gulf Views Paradise Sur Mer

Longboat Key, Florida, United States

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Exceptional(36)

$861.14

/ Nightly

Condo

3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!

Longboat Key, Florida, United States

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Exceptional(36)

$1148.84

/ Nightly

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Beach Front Condo on Gulf of Mexico

Longboat Key, Florida, United States

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Exceptional(36)

$2112.85

/ Nightly

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Luxury Beachfront Living - St Regis Waterfront Residency - Longboat Key - Sunset Reflections

Longboat Key, Florida, United States

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Exceptional(36)

$1196.70

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Condo

Renovated Beachfront 2 Bedroom Condo by FVC

Longboat Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(36)

$739.37

/ Nightly

Condo

Stunning gulf front 6th floor Longboat Key Condo with endless views - Once Upon A Tide

Longboat Key, Florida, United States

Bed

Bath

Sleeps

34228, Florida, United States Vacation Rental Condos By Owner - Page 25

$318.65

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$327.03

$193.48

$474.98

$302.06

$531.37

$182.62

$346.08

$352.82

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