Beachfront holiday rentals in Naples

3 blocks to the Gulf, 3 Blocks to Fifth Ave

A duplex located a stone’s throw from 5th Ave South and 3rd St South. Three blocks on a well-lit sidewalk bring you to the warm waters, white sands, and magical sunsets of the Gulf from this two-bedroom we call 385. This independent rental, new to Airbnb this season, has a spacious living room, dining table, a full eat-in kitchen, two full bathrooms, laundry in the unit, and on-site parking. We provide beach supplies, internet, smart televisions, and enough basic supplies to get you started.

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Cooks kitchen. Amazing views of the Gulf w/5 star ratings! 3-day min. New hurricane windows, nicely furnished with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1:King bed ensuite, smart TV. BR 2: 2 tw. beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow sm. dog.

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a perfectly located 1 bedroom condo in the heart of Old Naples, just a 1/2 block from vibrant 5th Avenue with its restaurants, boutiques, and cafés, and only four short blocks to the beach. Set in a charming Old Florida building surrounded by multi-million-dollar estates, the condo offers access to a heated pool perfect for a refreshing dip after a day at the beach. Inside, you’ll enjoy fast WiFi with a dedicated workspace, and the convenience of keyless, contactless entry.

Private Waterfront Paradise 3/3 Pool Home on Canal

This tropical paradise waterfront 2-story pool home is well-equipped with all the essentials needed for an amazing Florida getaway. Gather in the serene, private back yard where an expansive heated pool awaits you. Watch dolphins swim by the dock as you lounge and sunbathe. Enjoy free use of the many kayaks, paddleboards and bikes (for kids and adults). Perfectly located close to restaurants and multiple white-sand beaches, this North Naples retreat has everything you have been looking for.

Tivoli Paradise Salt Pool & Spa Villa with a Water

Step into the comfort of this luxurious 4BR 3Bath waterfront pool villa in Naples, FL. Situated in a tranquil, family-friendly neighborhood of Briarwood, it promises a serene retreat, close to golf & country clubs, restaurants, and numerous attractions. ✔ 4 Comfy BRs (3 BR w King beds! 1 BR w two TWIN XL Beds) ✔ Salt Spa and Pool ✔ Lake view ✔ Bicycles ✔ High-Speed Wi-Fi PETS REQUIRE APPROVAL PRIOR TO BOOKING ($300/small dog). Pool heat $25/night June 1-Sept 30, $35/night Nov 1-May 31

Lovely 1 BR Condo steps away from Bonita Beach!

Welcome to our Bonita Beach Paradise that we would love to share with your family! This unit is newly renovated and all appliances, furniture, and fixtures are brand new! Enjoy ocean & 🌴 views from the condo! Equipped with all the furnishes you need to enjoy your vacation! 1 Bedroom + 1 Bath. Along with a pull out sleeper couch. Refrigerator, Oven/Range, Microwave, and in unit washer and dryer. Exactly a .25 mile walk to the beach, and within walking of local restaurants!

Blue Beach Bungalow

3 large bedrooms (3 king sized beds) with TV in everyroom, plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics,

Westshore Naples Cay #202- Stunning Ocean view

Relax with the whole family at this peaceful location. Located in the neighbourhood of Naples Cay, our condo will sweep you into the charm and excitements of Naples - the capital of happy hours and live music! Our spacious condo is beautifully furnished, featuring top of the line appliances. The open balcony is the highlight of the space with beautiful views of the beach! Stay cool with central A/C and wind-down comfortably with king size beds in BOTH rooms!

Lovers Key Beach Club Private Beach

Minimum age to book is 25 please. 7 night minimum Lovers Key beach front, with all of Lovers Key State Park just across the street which also has beautiful white, sand beaches. Beach...Dolphins...Fishing...Kayaking...Biking...right out your door! Beautiful sunrise and sunsets from the condo. Private beach with private pool. Next door to multiple beaches, restaurants and bars within short distance. Private enough to be out of the hustle and bustle.

206C Gulf Water Views + 2 bikes + beach gear

Beachfront & Gulf Water Views at Estero Beach & Tennis Club 206C Wake up to unobstructed Gulf views in this 5-star Fort Myers Beach condo! Enjoy early check-in, no checkout chores, and every comfort—from a king GhostBed, full kitchen with dishwasher, free high-speed WiFi, heated pool, tennis/pickleball courts, BBQ grills, free parking, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.

The Club at Naples Cay 501 - Gulf Views

Welcome to our condo with amazing Gulf Views and an old Florida feel. We are located on the 5th Floor of The Club at Naples Cay. Forget your worries in this spacious & serene space, watch the beautiful sunsets from our private balcony and listen to the waves as the sun rises. We are just a short walk from our private beach with amazing views. Our complex is a gated community that provides 24-hour security.

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.