
Family-friendly holiday rentals in Estero Bay
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Top-rated family-friendly rentals in Estero Bay
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Remodeled 4 BR 3 Full Bath Sunshine Getaway
A perfect place for couple's or families. This home boasts 2 master suites with large, covered Lani with heated pool (Nov-March 85°). A total of 7 smart TVs. Enjoy preparing a family meal in the large fully equipped kitchen with double oven and plenty of counter space. Enjoy a bike ride on one of 4 bikes or Cornhole that's provided as well as other games and beach accessories. House sits on a quiet cul-de-sac for relaxing. Absolutely no parties or events! Max Guests on property at ANY time is 8!
5.0 out of 5 average rating, 102 reviews
Your Private NaplesBeach Getaway
🌴 Private Oasis 3 mins from The Beach 🌊 Welcome to our slice of paradise in Naples Park, Florida! Nestled 3 minutes away from the pristine sands of Naples Beach, world-famous Mercato Shops & Dining, and Publix/Walmart. Only 15 minute north of 5th Ave Downtown District. Our renovated home features a new privately fenced lit backyard with new heated saltwater pool, a custom miniature golf zone, and many outdoor games for every guest 😃 Simply the perfect cozy retreat for your beach getaway⛱️
5.0 out of 5 average rating, 141 reviews
Paradise on Estero Bay
Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.
4.95 out of 5 average rating, 164 reviews
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.
5.0 out of 5 average rating, 9 reviews
*Relaxing and Fun Pyramid Home in Ft Myers (7048)
Get ready for a unique vacation in a fully equipped pyramid home!! Enjoy exploring all of southwest Florida and then return home where you can relax on your own private patio or jump in the natural spring water lake! Located in south Ft Myers, easy distance to most attractions, 15 miles to beaches!! -Free WIFI -washer dryer -full kitchen -2 patios with dining area -self check in with lock box -perfect for families, great friends, couples -Beach gear provided -2 bedrooms/ 1 bathroom unit
4.93 out of 5 average rating, 304 reviews
Fort Myers Beachfront Escape - Walk to the Sand!
Wake up to the sound of waves, grab your coffee, and walk barefoot to the beach. Our cozy, sunlit apartment is perfect for couples, solo travelers, or remote workers craving some Florida sunshine. Enjoy from the beautiful sunsets and watch the dolphins swimming on the bay! A beautiful beachside apartment with private beach and heated pool. Located near the quiet Lovers Key State Park. Beautiful bike trails, affordable kayak, boat, and paddle boarding. Perfect Florida oceanic getaway !
5.0 out of 5 average rating, 17 reviews
Elegant Beachside Luxury Home Awaits!
This stunning Bonita home is steps from the beach. It combines modern luxury with artistic flair. The home features a striking wave stained-glass window and cozy sitting nook which provides an ideal spot to watch mesmerizing sunsets. The chef’s kitchen flows into the great room and dining area, where a large picture window frames serene views of palms. The home has a generous outdoor deck. It features three beautiful bedrooms and two full bathrooms, each designed luxuriously.
4.92 out of 5 average rating, 60 reviews
Bonita Retreat: Heated Pool - Minutes to Beach
We know that you’ll love it here – whether you spend your time lounging by our pool, or at beautiful Barefoot Beach, less than 3 miles away. Our home is close to everything, so many beautiful beaches, great shopping and world class restaurants. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. This is our own vacation home, so we’ve made every effort to make it as comfortable and convenient as possible.
4.99 out of 5 average rating, 151 reviews
Palm Paradise Retreat | Pool Oasis
Welcome to your private Southwest Florida retreat. This beautifully appointed 4-bedroom, 2-bathroom home features a screened-in pool, outdoor kitchen, covered lanai, and spacious indoor-outdoor living areas designed for relaxation and entertaining. Whether you're enjoying a day by the pool, grilling dinner outdoors, or exploring the area's beaches, shopping, and dining, this home offers the perfect setting for a memorable Florida getaway with family and friends.
5.0 out of 5 average rating, 10 reviews
Luxury Home, Steps to the Sand! Pet Friendly!
Breathtaking sunsets await from the second story wrap-around deck on this gorgeous coastal style newly built home located steps from Bonita Beach and the famous Doc's Beach House! This home features a premier location and luxury stay all in one. Walk just steps to the beach, rent a boat, paddleboard, jet ski, cabana or beach loungers just across the street at Docs or enjoy an incredible meal at one of the areas great local restaurants just mins from the door!
4.98 out of 5 average rating, 112 reviews
Lovers Key Resort, Fort Myers Beach - Awesome
Fort Myers Beach and Lovers Key State Park are what you come to Florida for. Miles of Pristine beaches with the lovely white sand you want to walk upon. Great hiking and biking trails. A plethora of restaurants and things to do. Watch the Dolfins playing in the bay from your balcony. The wildlife is beautiful all times of the year and of course the Beach. Big wide stretches of beach to walk and play on. Come to Ft Myers Beach and ENJOY
4.81 out of 5 average rating, 185 reviews
Walk to The Ritz & Beaches, 2 Mstrs w Kings, Pets
Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...
4.99 out of 5 average rating, 156 reviewsPopular amenities for Estero Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Southern Comfort - Updated Waterfront Condo
4.87 out of 5 average rating, 102 reviews
Luxury Canal Oasis | Pool + Spa + Walk to Beach
4.96 out of 5 average rating, 121 reviews
Heated Pool + Hot Tub |3BR | Large Pool|Sleeps 10
4.96 out of 5 average rating, 101 reviews
Oasis Naples Condo 2BR/2Bath
4.87 out of 5 average rating, 129 reviews
Paradise on canal minutes to Ft Myers Beach/Gulf
4.99 out of 5 average rating, 118 reviews
Mid Island Home with Hot Tub 1 Block from beach!
4.96 out of 5 average rating, 157 reviews
Coastal Modern Retreat with Heated Pool and Spa
4.96 out of 5 average rating, 144 reviews
Naples Luxury Orange Blossom Oasis 4/3 Tiki Bar
4.95 out of 5 average rating, 107 reviewsFamily- and pet-friendly home rentals

Escape to your Happy Place-pool, 6 bed 2 1/2 bath
4.93 out of 5 average rating, 135 reviews
Whole cozy house
4.95 out of 5 average rating, 407 reviews
Sunside House, 3/2 Pool Home in Gated Community
4.99 out of 5 average rating, 143 reviews
#Closest2Beach - 3BD/3BA Oasis by RITZ BEACH GOLF
4.86 out of 5 average rating, 155 reviews
Tiki Pool House | 10 Min to Beach | Sleeps 14
4.79 out of 5 average rating, 136 reviews
Del Mar Villa
4.89 out of 5 average rating, 335 reviews
Heated Saltwater Pool Oasis, Lanai, Bonita Springs
4.97 out of 5 average rating, 113 reviews
*Naples Hideaway* - Peaceful Near Barefoot Beach
4.96 out of 5 average rating, 221 reviewsFamily-friendly home rentals with a pool

LUX Villa w/ Private Salt Water Pool, Lanai, Canal
4.99 out of 5 average rating, 266 reviews
Cozy 2 bedroom on the canal with pool and hot tub!
4.78 out of 5 average rating, 18 reviews
The Heron House
5.0 out of 5 average rating, 22 reviews
4-BR Family Home • Pool • Beach Access Across Stre
4.92 out of 5 average rating, 12 reviews
Large Home Steps to Beach, Heated Pool & Game Room
4.97 out of 5 average rating, 38 reviews
The Great Escape Beach House/ Pool/ Dock
4.98 out of 5 average rating, 44 reviews
Winter deal! Heated Pool/Game Rm/Close to beaches!
5.0 out of 5 average rating, 83 reviews
Barefoot Breeze 2
5.0 out of 5 average rating, 48 reviewsDestinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- St. Augustine Holiday rentals
- Davenport Holiday rentals
- Key West Holiday rentals
- Waterfront rentals Estero Bay
- Beachfront rentals Estero Bay
- House rentals Estero Bay
- Condo rentals Estero Bay
- Apartment rentals Estero Bay
- Luxury rentals Estero Bay
- Rentals with beach access Estero Bay
- Villa rentals Estero Bay
- Rentals with pools Estero Bay
- Rentals with a hot tub Estero Bay
- Family-friendly rentals Lee County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Naples Beach
- Captiva Island
- Englewood Beach
- Lovers Key Beach
- Florida Gulf Coast University
- Tigertail Beach
- Stump Pass Beach State Park
- Bowman's Beach
- Montura Ranch Estates
- Jetblue Park
- Barefoot beach Bonita Springs,FL
- Bonita National Golf & Country Club
- Edison & Ford Winter Estates
- The Naples Pier
- Boca Grande Pass
- Yacht Club Public Beach
- Ave Maria University
- Coconut Point
- Clam Pass Park
- Delnor-Wiggins Pass State Park
- Bunche Beach
- Barefoot Beach State Preserve
- Coral Oaks Golf Course
- Lovers Key State Park





