
Holiday rentals with a pool in Estero Island
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Top-rated rentals with a pool in Estero Island
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Ft Myers Beach & Lovers Key State Park- FANTASTIC!
BEACHES ARE OPEN! Beautiful Views, large unit, Enjoy the sun, beach, and excitement of Florida. Lovers Key State Park, beautiful beaches, hiking & biking trails, Ft Myers Beach, white sand, many activities. Views of the gulf & bay area. Exercise room, wifi, great swimming pool- the beaches & trails you come to Florida for. Ft Myers beach has the white sand you think of when visiting Florida. The Gulf Coast Beach, and Lovers Key State Park are there for your enjoyment. Great place for Memories

Salt Air Gulf View Pool Condo Steps from the Beach
This 2-bed, 2-bath condo has EVERYTHING for your sunny beach getaway! The master bedroom has a king bed and ensuite bathroom for privacy, while the second bedroom has 2 twins next to another full bathroom. Just steps from the white sand beaches with beach towels and chairs provided. Enjoy the pool or private balconies while you unwind and soak up the sunshine. A short walk to Publix and the island's favorite hangout, Junkanoo. Note: this second-floor unit’s elevator is currently out of order.

Gorgeous Beach Residence with Pool, Spa, and Bikes
Welcome to Margarita Mansion! This intimate four-condo development features a large heated pool, spa, and bikes, all within walking distance to the beautiful white sandy beaches of Fort Myers Beach, FL. This listing is for unit 3 at Margarita Mansion, which is a 2/2 apartment with kitchen and pool/spa access. Pet friendly with a sleeping capacity of up to four guests, this property is perfect for those seeking an amenity rich accommodation with private patio and close proximity to the beach!

Beachfront @ Elevate in the Sun!
Welcome to ELEVATE IN THE SUN! Where an elevated experience is waiting. Premier Host (Other Site)-4.8* The unit boasts a completely remodeled kitchen with quartz countertops, brand new appliances including a dishwasher (very rare), brand new living room furniture, and new A/C and music surround sound streaming via Amazon Alexa and Apple Music. Sunrises are included each morning on your private balcony and sunsets are breathtaking down on the beach with toes in the bright white sand.

Vacation Villas #132 Second Floor Beachfront Condo
We are back! Everything in the apartment is all brand new - be the first to experience our newly renovated space! Vacation Villas is the northernmost building on the island, with a secluded beachfront for your enjoyment, but only a short one mile walk to 'Times Square' - the heart of the island. Outdoor living at its best: on the beach, at the pool, on the private lanai, or cooking in the grilling area. Sink your toes in the powdered sugar sand and you will never want to go anywhere else!

Just Beachy • Pool • 2 Kings+ • 3 Min to Beach
Personally hosted by Paul & Alicia of Dancing Palms Vacations, this brand-new home offers Gulf views from the front porch—just steps from the white-sand beach. The 3BR/2BA retreat sleeps 8 with 2 KING bedrooms, a private heated pool, and a fenced outdoor living/dining area with TV and boutique coastal hotel vibe. Enjoy all-new furnishings, games, and beach gear. Open-concept living/kitchen/dining with 85” smart TV. Family-friendly and walkable to bars, restaurants, shops, and the marina.

Seabreeze Hideaway
Located in Sun Retreats Fort Myers Beach (formerly Indian Creek), just 3 miles from Fort Myers Beach, Bunche, and Sanibel Island, and Margaritaville. The property offers amenities, including pools, pickleball, tennis, and numerous activities. It’s a great location, away from the main beach traffic but still close to shopping. The trolley also stops right at the entrance. The bungalow features a fully equipped kitchen and allows one pet up to 20 pounds. An occupant must be 35 or older.

Mango Villa - Steps away from beach / private pool
We're Back! Fully Renovated in 2023! Welcome to the Mango Villa located at 150 Mango Street, Fort Myers Beach. 2 bedroom and 1 full bathroom villa. Steps away from the beach where paradise is waiting for you. Centrally located at the North end of the island. Walk to Times Square to enjoy shopping and dining. Close to all Fort Myers Beach has to offer while also located on a quiet residential street, this home is perfect for those that demand both proximity and tranquility!

Beachfront Bliss!
Experience the ultimate Fort Myers Beach getaway in our charming 2B/2Ba condo overlooking the beach! This retreat features a king master suite and second bedroom with full and twin beds. Enjoy modern walk-in showers, fully equipped kitchen boasting SS appliances and quartz tops. Stay connected with high-speed Wi-Fi, unwind on the balcony with stunning Gulf views, stroll along the beach, or explore the vibrant Times Square area. Your perfect beach escape awaits!

Ocean View Steps to the Beach - Seventh Heaven
Seventh Heaven Seventh Heaven is a peaceful beachfront retreat on the seventh floor, offering stunning Gulf views and easy beach access. This one-bedroom condo accommodates up to 4 guests, featuring a private balcony, modern kitchen, and spacious living area. On-site amenities include tennis courts and a coin-operated laundry. No pets allowed. Minimum age of 25 to book. Smoking is prohibited. 7-day minimum rental. Shared laundry facility.

Gulf Water Views + 2 bikes, beach gear weekly stay
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.
Popular amenities for Estero Island rentals with a pool
House rentals with a pool

Modern Oasis pool paradise

The Great Escape Beach House/ Pool/ Dock

Beach escape! Walk to the square! Steps to beach!

Luxe Cape Coral Escape w/ Heated Pool & Game Room

Waterfront Pool Home. Minutes to Sanibel & Beaches

Modern 3 bedroom 2 bath Beach House on FMB Island

Boater’s Paradise-Stunning Sunsets! Games Room!

Canal-front Paradise Retreat
Condo rentals with a pool

3BR BeachCondo | Gulfside Pool | Hot tub | Sleep 8

Steps to Beach! Heated Pool!

Dolphins and Water Views at L’Amour Coastal Condo

Cathy Condo

Serene Ocean View Escape at Sundial Resort

Lover's Key Resort Unit #807

100+ 5 Star Reviews and Right on The Beach!

Beach Front Condo, Amazing Gulf & Beach Views!
Other holiday rentals with a pool

Beach Sweet @ Casa Corine FMB#23-0068

Luxury Waterfront Home • Pool • Dock • Near Beach

Front Gulfview superb condo fully remodeled

Backyard Dream-Oasis! - Heated Pool

Heated pool, canal, outdoor kitchen & walk 2 Beach

Immaculate Beachfront Sanctuary!

Lovers Key Beach Club Private Beach

Beachfront Bliss | 2BR/2BA | Sunset Views
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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Englewood Beach
- Stump Pass Beach State Park
- Clam Pass Park
- Tigertail Beach
- Bonita National Golf & Country Club
- Heritage Bay Golf & Country Club
- Blind Pass Beach
- Esplanade Golf & Country Club of Naples
- Edison & Ford Winter Estates
- Del Tura Golf & Country Club
- Boca Grande Pass
- Florida Gulf Coast University
- Bunche Beach
- Delnor-Wiggins Pass State Park
- Talis Park Golf Club
- Stonebridge Country Club
- Jetblue Park
- Bowman's Beach
- Manatee Park
- Coral Oaks Golf Course
- Sun Splash Family Waterpark




