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

Longboat Key-OCEAN FRONT- on the beach
My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

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 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.

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.

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Silver Sands By the Sea: Open Today - Wed $150/nt!
This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

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!

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!

Quiet Beachfront Bungalow on Florida’s Gulf Coast
Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Bradenton Beach Sunsets 1, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

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 unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

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 waterfront rentals
Waterfront apartment rentals

Newly Remodeled Beachfront Studio - On the sand!

Sweet Retreat at Shorewalk!

Las Palmas Beach Rentals Unit 1

Ocean Front Condo!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Siesta Premier Location - The 'Calm of Siesta'

Popular Beachside Studio w Relaxing Patio & Palms!

Serenity on the Manatee
Waterfront house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Bayfront Beach access with Heated Pool!

Tranquility on the bay.

Location! Beach Access/Trolley/ Restaurants!

Steps to a Private Beach Clearwater Belleair

Waterfront Pool Home Steps to Beach

*New* Waterfront Retreat: Pool, Spa, Dock & Views

Walk to it all! Restaurants + Heated Pool +Beach!
Waterfront condo rentals

Relax in a Newly Renovated Beach Front Paradise

COASTAL CHIC! Luxury Apartment with Oceanviews

Luxury 3/3 Margaritaville Resort

A&A's Paradise near IMG & Anna Maria beaches

2/2 Newly remodeled Beach Front - Sunset Vistas

The Seabreeze Cottage with peaceful water views

Spectacular beach to bay views from this resort.

Sea Side Sunsets Unit C
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.ﺇ856 | ﺩ.ﺇ1,036 | ﺩ.ﺇ1,124 | ﺩ.ﺇ900 | ﺩ.ﺇ727 | ﺩ.ﺇ797 | ﺩ.ﺇ918 | ﺩ.ﺇ830 | ﺩ.ﺇ727 | ﺩ.ﺇ760 | ﺩ.ﺇ841 | ﺩ.ﺇ944 |
| 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 waterfront rentals in Longboat Key

Total vacation rentals
Explore 240 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 4,520 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
210 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
230 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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- Anna Maria Island
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