
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.

Beachfront Anna Maria Island w hot tub & Gulf view
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

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.

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity on sunny Siesta Key!

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.

Tropical Courtyard Paradise on St. Pete Beach
Charming, cozy, well-appointed/fully stocked ground floor 1 Bedroom Unit with its own Private Entrance, Courtyard & spacious heated Pool. A short 1 minute walk to either St. Pete's Gulf side Upham Beach or all the abundant Nightlife & Restaurants on Gulf Blvd. Free WiFi(Spectrum) & 2 separate 32" HD TV's (Living Room sofa bed & Bedroom Queen bed), have all Premium movie, news, & sports channels. This Unit is affordably priced for the Budget Conscious desiring that Premium Beach Location.

Sun-Kissed Memories!
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

KING Bed + AMI Beaches + Beach Gear!
🎙️🦩Welcome to the Retro Flamingo! Your tropical 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 retro “Old Florida” themed condo!

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.

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.

Palm Bay Club! Resort Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Winter Storm Escape Sale Ocean View Steps to Beach
Escape to paradise at this newly renourished beachfront condo in Indian Rocks Beach! Enjoy breathtaking Gulf of Mexico views and stunning sunsets from your doorstep. Steps away from the beach, this condo offers unparalleled access to sun, sand, and sea. Explore nearby restaurants and bars, or simply relax and soak in the natural beauty. Perfect for a romantic getaway or a family vacation. Beach gear including towels, chairs and umbrellas is included!
Popular amenities for Longboat Key condo rentals
Weekly condo rentals

Modern 1/1.5 Waterfront at The Strand

AMI Island Paradise 2. 100 FlipFlop Steps to Beach

Lime Kiss A! 3 Bedroom, 2 Bathroom Home Just Acros

New! Beachfront Paradise! ~Heated Pool! Top Floor

Beautiful 2 bed/2 bath with intracoastal view

we are open for business, living the dream.

Quiet Waters D2: Beach Access, Pool & Sunset Bliss

Stunning Beach Views All Around...
Pet-friendly condo rentals

Short walk to beach 4, King bed, Dog Friendly

Siesta Key Condo: Beach, Pool & Village Fun!

Modern Studio · 5 min from Siesta Beach

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

Charming and Updated 1 Bedroom in Runaway Bay

Steps to the beach! Condo with pool at The Terrace

5209B Menorca Street - Siesta Key Village Condo

Private Beachside Kitchenette
Condo rentals with a pool

Tradewinds Deluxe North Cottage

Cheerful Oasis on Anna Maria Island

Anna Maria Island -walk to the beach!

Amazing beachfront View & balcony on Long Boat Key

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

Renovated Villa, Near Crescent Beach, Heated Pool

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

211 Beach House
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ867 | ﺩ.ﺇ1,025 | ﺩ.ﺇ1,065 | ﺩ.ﺇ962 | ﺩ.ﺇ720 | ﺩ.ﺇ727 | ﺩ.ﺇ786 | ﺩ.ﺇ731 | ﺩ.ﺇ676 | ﺩ.ﺇ735 | ﺩ.ﺇ881 | ﺩ.ﺇ988 |
| 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 ﺩ.ﺇ220 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 & 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

Wi-Fi availability
500 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!
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- Condo rentals Manatee County
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- Manasota Key Beach
- River Strand Golf and Country Club
- Hard Rock Casino
- Englewood Beach
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