
Condo vacation rentals in Longboat Key
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Top-rated condo rentals in Longboat Key
Guests agree: these condos are highly rated for location, cleanliness, and more.

Walk to Beach & Bay | 5 Minutes to AMI
Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.

Stunning BEACH FRONT Condo, KING Size Bed, Balcony
NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

Beachfront condo in paradise with hot tub AMI
You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

A&A's Paradise near IMG & Anna Maria beaches
Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

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.

Short Stroll to the Surf! ~ Make Memories on AMI
Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

Oceanfront LBK: Relax & Recharge!
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...!

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

Gulf Side Florida Charm 1/1 Condo 60 Steps To Sand
Step back in time at Postcard Paradise, a charming beachside cottage that captures the magic of Old Florida. Nestled just steps from the shore, our eclectic retreat feels like living inside a vintage postcard. Sun-faded colors, and tropical murals set a nostalgic mood, while modern comforts keep things easy and relaxed. Each cozy room is filled with hand-picked decorations, breezy linens, and quirky coastal finds, creating a one-of-a-kind space where every corner tells a story.

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.

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. Enjoy 2 free bikes day rental with booking!

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

Steps from Lido Beach & St. Armands Circle

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

Modern 1/1.5 Waterfront at The Strand

Gulf View ~Heated pool~Renovated~Coconuts 2 bed!

Sunset and Beach view unit 402

Longboat Key Bungalow

Amazing beach view! Entire unit renovated!

Oceanview Seaside Cottage | Walkout Beach Access
Pet-friendly condo rentals

Short walk to beach 4, King bed, Dog Friendly

Lovely Condo minutes from beach & King bed

Spacious 2BR/2BA Garden Condo w/ Heated Pool

Waterside Studio in the heart of TI, walk to beach

Luxury 3/3 Margaritaville Resort

Siesta Key Condo: Beach, Pool & Village Fun!

Modern Studio · 5 min from Siesta Beach

Casa de B.O.B ... Best on Beach
Condo rentals with a pool

Tradewinds Deluxe North Cottage

Cheerful Oasis on Anna Maria Island

Cozy 1BR Beach Condo on Siesta Key!

Beachfront Oasis / Pool, Beach Access & Ocean View

Siesta Key Walkout Beachfront Condo

Location! Gulf Condo @ S. Jetty 30 day minimum

Freshly Renovated Vacation Villa at Shorewalk

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $322 CAD | $381 CAD | $396 CAD | $358 CAD | $268 CAD | $270 CAD | $292 CAD | $272 CAD | $251 CAD | $273 CAD | $328 CAD | $367 CAD |
| 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 vacation rentals
Explore 500 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at $82 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
470 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
500 of Longboat Key vacation rentals include wifi 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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