Holiday rentals in Longboat Key

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.

Vitamin Sea Escape!

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!!!!

Salty Harbor AMI pool retreat near the Beach

Charming Salty 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 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

Turtle Shores Beachfront Oasis

Unwind in a paradise of crystal-clear waters, soft sands, and breathtaking sunsets. Start each day with a peaceful stroll along the shoreline, where waves gently lap at your feet. As the sun dips below the horizon, enjoy sunsets so surreal they remind you why vacations matter. At night, gaze at a sky full of stars, listen to soothing waves, and feel the ocean breeze. More than a getaway, this is pure bliss—where pristine, silky sands and ample privacy create the perfect escape.

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.

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 1% among Airbnb’s homes.

Secluded Bayside Gem with beautiful bay views

Sat to Sat Check in/out 7 day minimum rentals only. Jan-April we do not accept reservations with children of any age. Additional 6% Manatee County tax not included need to collect separately. Newly added Pickleball courts on premises. This secluded, beautifully decorated, bay front condo has expanded views of the Sarasota Bay. 2 min drive to the quiet, unspoiled white sand beaches of the Gulf of Mexico, short distance to great water front dining.

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.

Longboat Key Condo Directly 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 the Gulf front location. You;re right on the beach. Completely updated in 2017 with full kitchen, two and half baths and three 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)."