Beach condo holiday rentals in Sarasota

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.91 out of 5 average rating, 124 reviews

The Honeymoon Suite on Siesta Key Beach

This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

4.78 out of 5 average rating, 106 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

4.98 out of 5 average rating, 245 reviews

Island Time: Open Sunday, $225/nt+Fees!

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...!

4.86 out of 5 average rating, 133 reviews

Beach Retreat - Jamaica Royale Unit #52

Casually elegant condo fully remodeled in 2025, and very close to beach! One bedroom, one bath unit includes quartz kitchen counters, new appliances, king bed and relaxing patio. Perfect size for 2 guests! No need to cross busy roads to get to stunning white sand; just a 5 -10 minute walk along lush grounds which boast 3 heated pools. Beach gear provided, and unit is stocked with linens and kitchen utensils. Minutes away from Siesta Village and other wonderful dining and activities.

Condo in Pass-a-Grille Beach

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

4.99 out of 5 average rating, 172 reviews

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.9 out of 5 average rating, 230 reviews

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.

A beachfront pool area is shown under a bright sky, featuring palm trees and umbrellas around the pool. Guests are seen enjoying the water, with lounge chairs and colorful towels placed around the poolside. The ocean is visible in the background, completing the serene atmosphere.

4.86 out of 5 average rating, 153 reviews

Private Beach Siesta Key Resort Jamaica Royale

Jamaica Royale is a Beach Front Oasis, offering a private community with our own beach access and 3 heated pools . Enjoy our sidewalks, directly to the beach with no roads to cross; only residents are allowed onto the property, offering a family-safe paradise! Put your toes in the white sands of Siesta Key, where we have a private beach pavilion and lounge chairs! Look at our overview, to see our excellent location! We are in the first set of villas, closest to the beach.

A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.

4.98 out of 5 average rating, 134 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

4.88 out of 5 average rating, 137 reviews

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.

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

4.97 out of 5 average rating, 129 reviews

Private Beach with Loungers · 2 Pools & Bay View

Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.

4.93 out of 5 average rating, 161 reviews

Gulf Views | Walkable | Spacious

Spacious Gulf-view 2BR condo perfect for families & groups—featuring a rare 2-queen guest room, king master, and plenty of room to spread out. Walk to the beach, restaurants, coffee, and more—no car needed. Easy beach access + FREE loungers make beach days effortless. Heated pool, fast WiFi & fully stocked with beach gear. Clean, spacious & comfortable in a prime, walkable location. (Daytime weekday construction nearby may cause intermittent noise.)

An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.