
Vacation rentals with outdoor seating in Longboat Key
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Quick stats about vacation rentals with outdoor seating in Longboat Key

Total vacation rentals
Explore 380 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 7,780 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Vacation rentals with a pool
320 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wi-Fi availability
370 of Longboat Key vacation rentals include wi-fi 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 outdoor seating rentals in Longboat Key
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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

Island Time 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...!

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.

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

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

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.

Beach Front Madeira Beach
PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.
Popular amenities for Longboat Key outdoor seating rentals
House rentals with outdoor seating

Sarasota's Luxury Oasis

LBK Dreamin' Beach Bungalow

Siesta Serenity ~ Pool/Waterslide/Waterfront

"Little Siesta" - Farm home near Terra Nova

Heated saltwater pool near Siesta and Downtown

The Peachy Beach House, steps to the gulf

Villa Marisol: Beachfront, Mediterranean, Pool

True Island Living House/beach/water views
Apartment rentals with outdoor seating

On Private Beach! Full Kitchen Ground Level Unit 7

Casita Serena ~ A Unique Historic Hyde Park Home

Lido Key FL Studio/Efficiency 5

Hyde Park "Industrial-chic" with Private Backyard

Ohana Hale North B - 1 Bedroom

Serenity on the Manatee

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

High Tide @ Tides Inn
Condo rentals with outdoor seating

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

Relax in a Newly Renovated Beach Front Paradise

On the Beach; Siesta Key SunBum Studio

KING Bed + Anna Maria Island Beaches + Beach Gear!

Spectacular beach to bay views from this resort.

Steps to the beach! Condo with pool at The Terrace

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Short Stroll to the Surf! ~ Make Memories on AMI
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.ﺇ885 | ﺩ.ﺇ1,113 | ﺩ.ﺇ1,183 | ﺩ.ﺇ900 | ﺩ.ﺇ735 | ﺩ.ﺇ819 | ﺩ.ﺇ830 | ﺩ.ﺇ760 | ﺩ.ﺇ698 | ﺩ.ﺇ735 | ﺩ.ﺇ892 | ﺩ.ﺇ929 |
| 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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- 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
- Turtle Beach
- Lido Key Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- St Pete Beach
- Manasota Key Beach
- Anna Maria Public Beach
- Jannus Live
- Englewood Beach





