
Condo holiday rentals in Longboat Key
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Top-rated condo rentals in Longboat Key
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Waterfront Coastal Retreat | Steps from LBK Beach
Welcome to paradise - your tropical escape awaits! Wake up to island serenity in our brand NEW studio suite where you'll enjoy peaceful lagoon views from your private balcony. This gem, located in the coveted Longboat Key Resort Club, beautifully blends modern touches with coastal charm. Bask under the sun and enjoy private access to Longboat Key Beach and the heated resort pool which is just steps away. Perfectly positioned for relaxation, adventure, and exploring the best of Downtown Sarasota.

Beachfront Escape – Private Balcony, Gulf Views
Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

Spectacular beach to bay views from this resort.
Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Five Star Beachfront Condo Newly Renovated
A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

Near beach. Pool view. King bed. Daily rentals
The ‘pool view’ overlooks the swimming pool & has a private covered open porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a Smart TV. Separate bedroom with King size bed 3 mins walk to Crescent beach access #12 You can walk to a great choice of places to eat and drink Max 2 guests No smoking, No Pets, Great Location, Good Value.

Comfy Siesta Key Condo
Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Sun-Kissed Memories: Open Thursday, March 26th!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

Beachfront Resort, Ocean View, Pool, Tennis, Gym
Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Beachfront Condo in Exclusive Resort
The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

KING Bed + Anna Maria Island Beaches + Beach Gear!
⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

Sunset and beach view from your balcony Unit 403
A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.
Popular amenities for Longboat Key condo rentals
Weekly condo rentals

Siesta Key Village, Pool, Beach Access 4-min Walk

Spectacular Siesta Key Beachfront Condo

Siesta K- Kayak, Boat Dock, Pool, & walk to Beach

Beach Retreat III

Anna Maria Island -walk to the beach!

Siesta Oceanview Retreat-1 min walking to beach

Fully Renovated Waterfront Condo on Isla Del Sol

Bradenton Beach Best Vacation
Pet-friendly condo rentals

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

5213B Calle Menorca - Siesta Key Village Condo

A Coastal Retreat Steps From the Sea

Short walk to beach 4, King bed, Dog Friendly

Waterside Studio in the heart of TI, walk to beach

Modern Studio · 5 min from Siesta Beach

Resort living in paradise

Steps to the beach! Condo with pool at The Terrace
Condo rentals with a pool

Tradewinds Deluxe North Cottage

Beachfront Private Balcony. Heated Pool + Tiki Bar

Stunning Bay Views | Walkable Retreat

Foxtail Palm: *Luxe Pool Oasis *Steps from Beach

New! Beachfront Paradise! ~Heated Pool! Top Floor

Gulf-Front Condo with Sunset Views

White Sand Beachfront Condo with Stunning Sunsets

Brand New Everything! Private Beach & 3 Htd Pools!
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $333 AUD | $394 AUD | $410 AUD | $370 AUD | $277 AUD | $280 AUD | $302 AUD | $281 AUD | $260 AUD | $282 AUD | $339 AUD | $380 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about condo rentals in Longboat Key

Total holiday rentals
Explore 500 holiday rentals in Longboat Key

Nightly prices starting at
Longboat Key holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 4,360 verified reviews to help you choose

Family-friendly holiday rentals
380 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
470 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
500 of Longboat Key holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Longboat Key rentals

4.8 Average rating
Longboat Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
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- Vinoy Park
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