
Condo vacation rentals in Longboat Key
Find and book unique condos on Airbnb
Quick stats about condo rentals in Longboat Key

Total vacation rentals
Explore 470 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at €52 per night before taxes and fees

Verified guest reviews
Over 3,770 verified reviews to help you choose

Family-friendly vacation rentals
340 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
440 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
470 of Longboat Key vacation 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!
Top-rated condo rentals in Longboat Key
Guests agree: these condos are highly rated for location, cleanliness, and more.

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
Welcome to Mi Casa Siesta on 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
5.0 out of 5 average rating, 172 reviews
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!
4.96 out of 5 average rating, 112 reviews
NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.
4.95 out of 5 average rating, 146 reviews
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.
4.8 out of 5 average rating, 144 reviews
Island Time: Open Sept 29th-Oct 3rd, 4 Night Stay!
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...!
4.98 out of 5 average rating, 258 reviews
Turtle Shores Beachfront Oasis
Unwind in a paradise of crystal-clear waters, soft sands, and breathtaking sunsets. Start each day with a peaceful stroll along the shoreline, where waves gently lap at your feet. As the sun dips below the horizon, enjoy sunsets so surreal they remind you why vacations matter. At night, gaze at a sky full of stars, listen to soothing waves, and feel the ocean breeze. More than a getaway, this is pure bliss—where pristine, silky sands and ample privacy create the perfect escape.
4.87 out of 5 average rating, 67 reviews
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.
4.9 out of 5 average rating, 241 reviews
Beach Condo with Quiet, Private Beach
Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.
4.98 out of 5 average rating, 109 reviews
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.
4.88 out of 5 average rating, 139 reviews
Luxury 3/3 Margaritaville Resort
Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.
4.97 out of 5 average rating, 212 reviews
Cottage on Siesta Key Beachside & Stunning sunsets
Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!
4.92 out of 5 average rating, 171 reviews
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.
4.87 out of 5 average rating, 210 reviewsPopular amenities for Longboat Key condo rentals
Weekly condo rentals

2 Salty by Duncan Real Estate
5.0 out of 5 average rating, 5 reviews
Sunset and Beach view unit 402
5.0 out of 5 average rating, 36 reviews
Secluded Bayside Gem with beautiful bay views
4.97 out of 5 average rating, 72 reviews
Island property on Longboat Key by the Beach
4.9 out of 5 average rating, 51 reviews
Waterfront Coastal Retreat | Steps from LBK Beach
4.94 out of 5 average rating, 33 reviews
2/2 Beachfront, VIEWS, Pool, Private Beach Access
5.0 out of 5 average rating, 7 reviews
Sea Grape Inn #1- Beachfront Property
5.0 out of 5 average rating, 3 reviews
Second Floor Studio- Amazing Gulf Front Views
5.0 out of 5 average rating, 6 reviewsPet-friendly condo rentals

Beachfront Condo in Exclusive Resort
4.86 out of 5 average rating, 671 reviews
BEACHFRONT Condo - Belleair Beach Club - RENOVATED
4.72 out of 5 average rating, 548 reviews
Luxury Seashell Oceanfront Condo with Pool
4.9 out of 5 average rating, 119 reviews
5213A Calle Menorca - Siesta Key Village Condo
4.86 out of 5 average rating, 128 reviews
Amazing views on beachfront
4.91 out of 5 average rating, 488 reviews
Blanco at Sunset Villas on Anna Maria Island
4.93 out of 5 average rating, 160 reviews
2 Story Penthouse | Pool | Balcony | Gulf View 602
4.89 out of 5 average rating, 160 reviews
Short Stroll to the Surf! ~ Make Memories on AMI
4.99 out of 5 average rating, 160 reviewsCondo rentals with a pool

Beachfront Siesta Key | Gulf View + Private Beach
4.97 out of 5 average rating, 397 reviews
LIDO KEY 1 BR/1Bath Heated Pool 16
4.82 out of 5 average rating, 154 reviews
Gulf Views | Walkable | Spacious
4.92 out of 5 average rating, 166 reviews
Heated Pools & Spa · Private Beach + Bay Views
4.97 out of 5 average rating, 137 reviews
Anna Maria Island - 3 bedroom - 2 pools - Hot Tub
4.88 out of 5 average rating, 17 reviews
Bayfront • Rehabbed • Pickleball • Private Beach
5.0 out of 5 average rating, 9 reviews
Stunning water views at Crystal View Cove Beach Co
5.0 out of 5 average rating, 3 reviews
~Hot Dates, Cool Prices – Beach Access - Lrg Pool~
4.96 out of 5 average rating, 51 reviewsWhen is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €226 | €327 | €331 | €305 | €235 | €236 | €186 | €173 | €160 | €174 | €209 | €234 |
| 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 |
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- Anna Maria Island
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- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Amalie Arena
- Turtle Beach
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