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

Gulf front best sunset views, Anna Maria Island
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

Steps to the beach! Condo with pool at The Terrace
Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

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.

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.

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED
THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

Island Time on LBK!
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.

Beach Front Madeira Beach
PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. And our swimming pool is currently closed for renovations as well. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.

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.

The Beach Condo #107 Beachfront Full View
Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.
Popular amenities for Longboat Key condo rentals
Weekly condo rentals

Tradewinds Deluxe North Cottage

Amazing beachfront View & balcony on Long Boat Key

Beachfront Newly Remodeled 2/1 -Right on the beach

Gulfview Retreat | Heated Pool | Steps to Gulf

2 Bed/2 Bath Waterfront Condo With Dock Sleeps 6

Luxury 2 bedroom Beachfront Condo by FVC

Newly Rehabbed • Pickleball/Tennis • Beach Access

we are open for business, living the dream.
Pet-friendly condo rentals

Short walk to beach 4, King bed, Dog Friendly

Luxury 3/3 Margaritaville Resort

Modern Studio · 5 min from Siesta Beach

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Lake View 1BR Condo | Heated Pool Near Siesta

Casa de B.O.B ... Best on Beach

Amazing views on beachfront

Walk to Beach, Bars, and Restaurants Nearby
Condo rentals with a pool

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Foxtail Palm: *Luxe Pool Oasis *Steps from Beach

The Honeymoon Suite on Siesta Key Beach

Beachfront Oasis / Pool, Beach Access & Ocean View

New! Beachfront Paradise! ~Heated Pool! Top Floor

Gulf Strand Beach Resort

Sandcastle Dreams

Updated in Beach Castle, Private Beach Access
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $358 CAD | $517 CAD | $523 CAD | $360 CAD | $270 CAD | $272 CAD | $294 CAD | $274 CAD | $253 CAD | $275 CAD | $330 CAD | $370 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 530 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at $83 CAD per night before taxes and fees

Verified guest reviews
Over 3,610 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
490 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
520 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- House rentals Longboat Key
- Rentals with an EV charger Longboat Key
- Beach condo rentals Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Fitness-friendly rentals Longboat Key
- Rentals with pools Longboat Key
- Beach house rentals Longboat Key
- Beachfront rentals Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Rentals with a hot tub Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washer and dryer Longboat Key
- Waterfront rentals Longboat Key
- Rentals with lake access Longboat Key
- Rentals with an accessible height toilet Longboat Key
- Cottage rentals Longboat Key
- Rentals with a firepit Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Townhouse rentals Longboat Key
- Rentals with a patio Longboat Key
- Condo rentals Manatee County
- Condo rentals Florida
- Condo rentals United States
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Turtle Beach
- Lido Key Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- St Pete Beach
- Anna Maria Public Beach
- Manasota Key Beach
- Jannus Live
- Englewood Beach





