Vacation rentals in Longboat Key
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Top-rated vacation rentals in Longboat Key
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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).
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.
Entire Standalone Villa,1.2k sf,1 block Lido Beach
Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!
Short Stroll to the Surf! ~ Make Memories on AMI
Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.
The Mango House Beach Cottage
Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!
Breezy Harbor AMI pool retreat near the Beach
Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our open calendar -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024
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...!
Bradenton Beach Sunsets 3, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 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.
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
Best views of the beach from your balcony Unit 301
Welcome to Paradise! Unit 301 with unobstructed Mexican Gulf View. This is a corner condo, so you have more space and a side window view. We just repainted our apartment and renovated the bathroom. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. Enjoy the large living room area with a queen Murphy bed for extra comfort, there's plenty of room for 6 in this condo.
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 vacation rentals
Stay near Longboat Key's top sights
Longboat Key beachfront vacation rentals
Private Beachfront 2BR BUNGALOW*POOL*PETS ok
850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo
Tropical Beachfront Penthouse-Beach Cottages
Direct Ocean View Top Floor Renovated. 2BR, 2 Bath
Waterfront Pool Home Steps to Beach
Siesta Key Beach Front Condo
Stunning BEACH FRONT Condo, KING Size Bed, Balcony
𖤓Updated Stilt home: just steps to the beach!𖤓
Longboat Key house rentals
Be an AMI
2nd House from the Beach with No Roads to Cross
Tranquility on the bay.
The Peachy Beach House, steps to the gulf
St Armand's Mid-Century Oasis
Turtle Nest: Private Oasis w/Hot Tub+5 mi to beach
Private Heated Pool, Turfed Putting Green Retreat
STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!
Longboat Key condo rentals
Beautiful White Sand Siesta Key Beach
Sea Shell Ocean View On Beach Walk Everywhere Pool
Short walk to beach 4, King bed, Dog Friendly
Spectacular beach to bay views from this resort.
Steps to the beach! Condo with pool at The Terrace
Oceanview Seaside Cottage | Walkout Beach Access
Five Star Beachfront Condo Newly Renovated
Island property on Longboat Key by the Beach
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.ﺇ1,003 | ﺩ.ﺇ1,006 | ﺩ.ﺇ918 | ﺩ.ﺇ720 | ﺩ.ﺇ735 | ﺩ.ﺇ771 | ﺩ.ﺇ727 | ﺩ.ﺇ672 | ﺩ.ﺇ727 | ﺩ.ﺇ834 | 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 |
Frequently Asked Questions
What are the best places to stay in Longboat Key?
Guests often look for vacation rentals near the Gulf beaches or around the bay side for convenient access to water activities and dining. The north and south ends of the island are frequently suggested for their laid-back atmosphere and scenic views.
What are the best things to do in Longboat Key with kids?
Families frequently explore the beaches for shell collecting and gentle waves, walk the nature trails at Joan M. Durante Park, or try paddleboarding in calm waters. Many local restaurants have kid-focused menus and outdoor seating.
What are some of the best things to do in Longboat Key?
Enjoy white sand beaches, explore the natural habitats at Joan M. Durante Park, or rent a kayak for a peaceful paddle along the shoreline. The island’s local restaurants and small galleries also capture the coastal community’s character.
How is the weather in Longboat Key?
Longboat Key has mild winters around 51–72°F (10–22°C), with spring bringing warmer, pleasant days. Summers become hot and humid, reaching up to 91°F (33°C), and occasional rainfall is common from late spring through early autumn.
When is the best time to visit Longboat Key?
Late winter through spring is often recommended for dry, mild weather with temperatures around 55–83°F (13–28°C). Summer and early autumn bring higher humidity and rainfall, but also lush landscapes and fewer crowds.
What are the best places to visit in Longboat Key?
The island has scenic beaches, the Joan M. Durante Park with its boardwalks and gardens, and a lively waterfront area with local shops and restaurants. Exploring the bay by kayak or paddleboard is also frequently suggested.
What are some hiking trails in Longboat Key?
Explore the Joan M. Durante Park trails, which wind through native gardens and mangrove forests, or wander the pathways at local preserves for birdwatching and views of Sarasota Bay. Trails are generally flat and suitable for all ages.
What are some family activities we can do in Longboat Key?
Families often enjoy shelling on the beach, picnicking at local parks, or spotting wildlife along the trails at Joan M. Durante Park. Guided kayak tours and casual bike rides are also popular with visitors of all ages.
What are some of the best day trip ideas from Longboat Key?
Explore nearby Sarasota's art museums or lively downtown, visit historic fishing villages around the area, or discover the natural beauty of nearby nature preserves. Barrier islands and gardens just outside Longboat Key are also often recommended.
Are there any pet friendly accommodations available in Longboat Key?
Many vacation rentals on Longboat Key welcome pets, particularly in beachside cottages and private homes. Local parks and outdoor dining spaces often include dog-friendly areas, making it easy to explore together.
What are some local tips for visiting Longboat Key?
Consider bringing sun protection and reusable water bottles, as much of life on Longboat Key happens outdoors. Many shops and restaurants have a relaxed dress code, and exploring the island by bike is often recommended for a leisurely pace.
What is Longboat Key known for?
Longboat Key is known for its tranquil Gulf beaches, locally inspired seafood, and serene natural preserves like Joan M. Durante Park. The island has a relaxed atmosphere, often attracting those looking for a coastal retreat.
What are the best hidden gems to explore in Longboat Key?
Seek out quiet beach access points for peaceful shoreline walks, or visit local nature preserves with boardwalks through mangroves. Art galleries and small family-run restaurants around the island often highlight coastal traditions.
What are the best foods to try in Longboat Key?
Longboat Key is known for fresh seafood like grouper sandwiches, stone crab, and shrimp prepared with local flavors. Key lime pie is a frequently suggested dessert, and many spots feature locally sourced produce and citrus.
What should I bring for a trip to Longboat Key?
Pack swimwear, light layers, comfortable sandals, and sun protection such as sunglasses and a hat. A reusable water bottle and beach gear like a towel or snorkel set can help you make the most of the coastal setting.
What is the nightlife in Longboat Key like?
Longboat Key has a relaxed nightlife scene, with waterfront bars, live music at local restaurants, and venues that feature sunset views. Many visitors enjoy low-key evenings and outdoor lounges rather than late-night clubs.
What are the most popular events or festivals in Longboat Key?
Seasonal art fairs, seafood festivals, and holiday boat parades are frequently suggested activities in and around Longboat Key. Community markets and cultural events often take place during the cooler months.
Are there family friendly vacation rentals in Longboat Key?
Longboat Key has a variety of family friendly vacation rentals, including multi-bedroom homes, condos with pools, and properties near beaches or parks. Kid-focused amenities such as full kitchens and outdoor spaces are commonly available.
All about Longboat Key
Stretching between the Gulf of Mexico and Sarasota Bay, the barrier island of Longboat Key has attracted its share of sun-seekers, who can be found teeing off at the sweeping gulf-front golf courses or fishing in the mangroves for speckled trout. With Siesta Key to the south and Anna Maria Island to the north, Longboat Key has an upscale feel, with nice restaurants, luxury resorts, and 256 days of annual sunshine. At the northern tip is Beer Can Island, a popular picnic spot that’s prettier than its name might suggest; the untouched, white-sand beach is even accessible on foot at low tide. Paddleboarding, windsurfing, and other on-the-water activities beckon you into the Gulf. And when you’ve finally kicked the sand from your toes and are ready for some culture, you can visit the Ringling Museum of Art in Sarasota, which showcases the circus impresario’s vast collection of classic and modern European and American artworks.
What are the top things to do in Longboat Key?
St Armands Circle
This round little island shopping center just south of Longboat Key is home to high-end boutiques, art galleries, fine dining, and other urbane attractions. Surrounded by water on all sides, it makes for a perfect scenic day of shopping. Check the calendar for special events throughout the year.
Coquina Beach
Just a few minutes’ drive over the Longboat Pass Bridge, this relaxed white-sand beach at the southern end of Anna Maria Island is worth a visit for its scenic sunset views. Hunt for shells, play some beach volleyball, and keep an eye out for passing pods of dolphins.
Quick Point Nature Preserve
A short (0.8-mile) walking trail wends its way through 34 acres of protected wetlands and mangrove lagoons. If you’re lucky you might spot a dolphin swimming through the seagrass, or watch a heron, egret, or ibis hunting for its dinner.
Quick stats about vacation rentals in Longboat Key
Total vacation rentals
Explore 1,010 vacation rentals in Longboat Key
Nightly prices starting at
Longboat Key vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees
Verified guest reviews
Over 11,250 verified reviews to help you choose
Family-friendly vacation rentals
780 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 170 rentals that welcome pets
Vacation rentals with a pool
830 properties feature pools
Rentals with dedicated workspaces
380 properties have a dedicated workspace
Wi-Fi availability
990 of Longboat Key vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Free parking on premises, and Beachfront 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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