
Waterfront vacation rentals in Longboat Key
Find and book unique waterfront rentals on Airbnb
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).

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

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.

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

Oceanfront 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...!

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.

Newly Remodeled Beachfront Studio - On the sand!
ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

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!

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!

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.

New Year Sale! Ocean Views!-15 Steps To The Sand!
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!

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.
Popular amenities for Longboat Key waterfront rentals
Waterfront apartment rentals

Sweet Retreat at Shorewalk!

Siesta Key - Poolside Suite - Studio - Free kayaks

Complete Renovation-everything new! Amazing views

Ocean Front Condo!

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

20 Steps To The Beach | Private 1BR Unit On Beach

Siesta Premier Location - The 'Calm of Siesta'

Serenity on the Manatee
Waterfront house rentals

Gulf Front! Beach Sunsets+ Walk to Bridge St Pier!

Beachfront Getaway in Siesta Key

Beautiful Lake View Home - Close Beaches / IMG

Waterfront Pool Home Steps to Beach

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Superhost! Fully Renovated Sarasota Home

Ocean Views - Spacious Unit, Bonus Loft & Hot Tub

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI
Waterfront condo rentals

Gulf-View 2BR/2BA Beach Condo!

Peaceful Longboat Getaway |2BR Condo + Bay + Beach

Sea Shell Ocean View On Beach Walk Everywhere Pool

Villa Al Golfo Pristine Waterfront Oasis

Spectacular beach to bay views from this resort.

Oceanview Seaside Cottage | Walkout Beach Access

Beach, dolphin/manatee sightings, fishing, sunsets

~Shore Thing~ Coastal Exquisite Waterfront 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 | € 199 | € 240 | € 261 | € 209 | € 169 | € 185 | € 213 | € 193 | € 169 | € 177 | € 195 | € 219 |
| 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 270 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 4,850 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
270 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!
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
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Beach condo rentals Longboat Key
- Beach house rentals Longboat Key
- Townhouse rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- House rentals Longboat Key
- Rentals with an EV charger Longboat Key
- Rentals with lake access Longboat Key
- Beachfront rentals Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Rentals with a patio Longboat Key
- Rentals with a hot tub Longboat Key
- Cottage rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washer and dryer Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Family-friendly rentals Longboat Key
- Condo rentals Longboat Key
- Rentals with pools Longboat Key
- Fitness-friendly rentals Longboat Key
- Rentals with an accessible height toilet Longboat Key
- Waterfront rentals Manatee County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- John's Pass
- Turtle Beach
- Dunedin Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Manasota Key Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Englewood Beach
- Adventure Island




