
Holiday rentals with outdoor seating in Longboat Key
Find and book unique rentals with outdoor seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Longboat Key

Total holiday rentals
Explore 380 holiday rentals in Longboat Key

Nightly prices starting at
Longboat Key holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 7,780 verified reviews to help you choose

Family-friendly holiday rentals
310 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Holiday rentals with a pool
320 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
370 of Longboat Key holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Longboat Key rentals

4.9 Average rating
Longboat Key stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with outdoor seating in Longboat Key
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Be an AMI
This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

[Sunny in Siesta] King bed+5 minute walk to beach
Your relaxing beach vacation awaits! Enjoy the island life from a freshly remodeled condo. Quick stroll to the #1 beach in the US. Public Access #12 (5 min walk) or hop on the free trolley to Siesta Beach & the Village. Can’t beat this location...Walk to Crescent Club, Captain Curt’s, Big Water Fish Market, Daquiri Deck & more. Beach gear includes- wagon., 2 chairs, small cooler and beach towels. 2 Bikes available to rent (40 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

Island Time on LBK: Open Sunday $195/nt + Fees!
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...!

Is this Heaven? No, it's Longboat Key
Newly renovated (November 2025) modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

Longboat Key Beach House
This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. It’s only one block to the beach access, convenience store, great restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has Pickleball and Tennis Courts, a junior Olympic POOL, gym, free bicycle rental and tiki bar. Minutes to Holmes, Bradenton and Coquina Beaches.

Pool, Shuffleboard, EV charg, Near beach, UTC mall
Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

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.

Modern 4BR Home *Heated Pool & Spa*
Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

Waterfront Condo, Close to Beach, with Boat Dock!
BEACH, BOAT, BIKE, FISH, KAYAK, TV/SPORTS, ENTERTAINMENT, FOOD, RELAX & ENJOY! Nestled between the highly sought after Anna Maria Island and St. Armand's Circle this amazing Longboat Key Boathouse offers just as much enjoyment as it does relaxation. This direct waterfront ground floor condo, packed with amenities, is just minutes away from the Gulf of Mexico. Come walk out of your back door to the intercoastal waterway, fish or sit and enjoy the tranquility.

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.

Bradenton Beach Sunsets 2, 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.

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 outdoor seating rentals in Longboat Key
House rentals with outdoor seating

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Sarasota's Luxury Oasis

ShoreSideSuites Stunning Gulf Views|Steps to Beach

NEW! Coconuts 106! Beach Front! Heat Pool!

Serenity Springs | Private Heated Pool + Waterfall

Private Heated Pool Retreat for Two Families

Beautiful Beach house! Heated pool and spa!

Sunset Shores: Stunning sunset views over the beac
Apartment rentals with outdoor seating

Cozy Coastal Getaway 2 min Walk to Beach & Village

Low Tide @ Tides Inn

On Private Beach! Full Kitchen Ground Level Unit 7

Come Enjoy Our Peaceful Retreat

Ohana Hale North A 2BR | 2.5 Blocks to Beach AMI

Hyde Park "Industrial-chic" with Private Backyard

ROYS PLACE Romantic, Private, Paradise!

Serenity on the Manatee
Apartment rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Siesta Key For Me @ The Palm Bay Club

On the Beach; Siesta Key SunBum Studio

Minutes to AMI | Walk to Beach & Bay

KING Bed + Anna Maria Island Beaches + Beach Gear!

Perfect Location in Siesta Key

Beach Front at “The Shore”

Steps to the beach! Condo with pool at The Terrace
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $309 SGD | $388 SGD | $412 SGD | $314 SGD | $256 SGD | $286 SGD | $289 SGD | $265 SGD | $243 SGD | $256 SGD | $311 SGD | $324 SGD |
| 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 |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- House rentals Longboat Key
- Townhouse rentals Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Rentals with an accessible-height toilet Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with pools Longboat Key
- Rentals with a patio Longboat Key
- Cottage rentals Longboat Key
- Rentals with a firepit Longboat Key
- Beachfront rentals Longboat Key
- Rentals with lake access Longboat Key
- Rentals with an EV charger Longboat Key
- Beach apartment rentals Longboat Key
- Flat rentals Longboat Key
- Rentals with beach access Longboat Key
- Apartment rentals Longboat Key
- Beach house rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Rentals with a hot tub Longboat Key
- Waterfront rentals Longboat Key
- Pet-friendly rentals Longboat Key
- Fitness-friendly rentals Longboat Key
- Rentals with outdoor seating Manatee County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating 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
- Lido Key Beach
- Turtle Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Sand Key Beach
- Dunedin Beach
- Cortez Beach
- Hard Rock Casino
- Manasota Key Beach
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Englewood Beach





