Beachfront holiday rentals in Estero Bay

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

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.

BONITA SPRINGS / FORT MYERS WATERFRONT 1 BEDROOM

Bonita Springs / Fort Myers Beach waterfront Lover's Key Resort with beach access. Large suite on the 6th floor. Sun filled floor-to-ceiling windows, captivating stunning bay and gulf views. Full size kitchen with breakfast bar and a large bathroom with jacuzzi tub plus separate shower. Bay front pool & hot tub, fitness room, business office, laundry facilities, beach access, and the award winning Flippers on the Bay waterside restaurant. A short drive or bike to State Park and public beach.

Sea Salt Beach Front Condo

Welcome to Sea Salt at Castle Beach, a newly renovated 2-bedroom, 2-bath Gulf-front condo designed for relaxation, comfort, and effortless coastal living. The open living space includes a comfortable pullout sofa. Each bedroom features its own ensuite with a walk-in shower, offering privacy and convenience for couples, families, or friends traveling together. The lanai spans the width of the condo, delivering breathtaking, unobstructed views of the Gulf and your private stretch of beach.

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,

Tommy Bahama House | 3-Bedroom Beachfront Retreat

The one and only Tommy Bahama House, bedrooms and three bathrooms, located directly on Bonita Beach in Bonita Springs, Florida. The elegance and beauty of Tommy Bahama House is apparent when you turn off Hickory Blvd. onto the paver driveway and see the ginger bread trim and lattice garage door's. You will immediately know why you choose to spend your vacation or Holiday on this beach front treasure. Look no more for that perfect beach front private home!

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.

Easy Breezy.

Steps from the beach! Easy Breezy is cute, cozy and clean.Unit is stocked with plenty of amenities and extras. Coffee provided for every morning of your stay! Daily vouchers are included for beach chairs set up for you ( VIP service) @ Bonita Jet Ski& Parasail across the street behind Doc’s beach house! ( a $22 per day value. Umbrella is NOT included) You can also receive ten percent off of any parasailing bookings! Come see how easy breezy it all is!

Waterfront with Saltwater Pool, Sauna, Cold Plunge

Experience the epitome of comfort and luxury in our exquisite 4-bedroom, 4-bathroom waterfront wellness retreat. Revel in the tranquillity of water views and be pampered by a host of rejuvenating amenities, including a therapeutic saltwater pool, a soothing sauna, and a refreshing cold plunge. This sanctuary is designed with top-of-the-line features and sumptuous interiors that ensure a restful and revitalizing stay beyond compare.

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.

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.

Rare walkout condo on Sanibel beach

READY FOR YOUR SANIBEL VACATION! Everything you need in this recently updated, comfortable 2 bedroom, 2 bath condo on beautiful Sanibel Island, Breakers West Unit A-6. Rare ground floor location; private walk-out patio leaves you just steps to the pool and less than a 2 minute walk to the world famous Sanibel beach on the Gulf of Mexico.