Holiday rentals with outdoor seating near Cortez Beach

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

AMI Cortez Beach Retreat "Views" Resort-style Pool

Resort-style Heated Pool w/ "Views Over the Water" at Beach + Bay Home - duplex upstairs unit • 65 steps to Cortez Beach + 7 miles of white Anna Maria Island sand! • $150,000 new large, heated pool with salt-water, spillover spa, sitting shelf, +built-in umbrellas. • Gulf + Beach + Bay Views inside home + deck • Paddleboard + Kayak • High-speed WiFi • 3 blocks to Bridge Street restaurants/bars/pier/shopping + listen to the Bell Tower Clock ringing each hour – live music! • Ping pong table

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...!

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.

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

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!

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach

COMPLETELY REMODELED! Aloha and welcome to our bit of old Florida. Ohana Hale Gulfside is 250 feet to the white sand beaches and turquoise water. Come join us for your vacation in the sun. The ideal bungalow for a couple or small family. This one bedroom, one bath with kitchenette is made for your best vacation memories. This unit is only one block to the beach and one block to the Bridge Street shopping district and the pier! This unit is one-pet friendly.

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

An unforgettable experience awaits you at this getaway apartment right on the white sand beaches of Anna Maria Island. Wake up every morning to the best views of the turquoise waves of the gulf and spend your days enjoying the warm waters, filling your social media with dolphin pictures and dramatic sunsets.

High Tide @ Tides Inn

Newly remodeled bay front home. Ideal for couples vacationing on the island. Quiet street yet close to lots of activities and fun. Park your car and don't move it for the vacation. Catch a free island wide trolley, rent a bike or just walk to the many area attractions.

Lovely 1 bedroom apartment with partial water view

Enjoy easy access to everything from this perfectly located home base.steps away from the beach .

ShoreSideSuites Stunning Gulf Views|Steps to Beach

🌊 Stunning Top-Floor Gulf Views | Steps to Beach | Unobstructed Sunsets