Holiday rentals in Longboat Key
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Top-rated holiday 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).
Turquoise Gem 1st Floor
Private beach access! *Designer Renovation* Single level, 4 min walk to bright white quartz sand. Welcome to UPGRADED beach paradise featuring: NEW full Stainless-Steel kitchen, NEW cabinets and granite countertops. LUXURY bathroom with granite top vanity, oversized shower tile with glass Mosaic Inlay and full glass enclosure. 65 inch 4k Roku Smart TVs with Super Fast 1000 MbPs internet. Very Posh Bedroom, KING SIZE Memory Foam Hybrid Bed. Pull-out QUEEN Size Memory Foam Bed in the living 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.
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!
Magical Guesthouse 1 mi from SRQ airport
@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum
Beach Condo: Open Next Weekend!
This charming seaside condo is 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort! To see all four of our listings, click on my Host photo and scroll down...!
New Modern Longboat Key*5 Steps to Sand*Heatd Pool
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!!!!
Waterfront 2BR 2BA | Pool - 10 min walk to Beach
A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.
The Peachy Beach House, steps to the gulf
The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels
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!
the Seaside 21
The Seaside 21 is a stylish waterfront villa in the heart of Holmes Beach on Anna Maria Island. Enjoy coffee on your private dock overlooking the bayou. Just 4 blocks to the beach, with shops and dining nearby. Bring your boat or have a captain pick you up for a day on the water. This weekly rental has been fully renovated and is centrally located. This island oasis is perfect for relaxing, fishing, exploring, and soaking in everything the island has to offer.
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.
Popular amenities for Longboat Key holiday rentals
Stay near Longboat Key's top sights
Other great holiday rentals in Longboat Key
Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Beachfront Corner Condo | Sunset Gulf Views
Location! Beach Access/Trolley/ Restaurants!
Cozy private beach condo
Beach Condo with Quiet, Private Beach
Waterfront Coastal Retreat | Steps from LBK Beach
Island Beach Paradise, Close to Everything, Bikes
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹21,685 | ₹24,564 | ₹24,654 | ₹22,495 | ₹17,636 | ₹17,996 | ₹18,895 | ₹17,816 | ₹16,466 | ₹17,546 | ₹19,795 | ₹22,405 |
| 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.
Quick stats about holiday rentals in Longboat Key
Total holiday rentals
Explore 930 holiday rentals in Longboat Key
Nightly prices starting at
Longboat Key holiday rentals start at ₹2,699 per night before taxes and fees
Verified guest reviews
Over 10,870 verified reviews to help you choose
Family-friendly holiday rentals
720 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 170 rentals that welcome pets
Holiday rentals with a pool
780 properties feature pools
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Wifi availability
920 of Longboat Key holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Free parking on premises 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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