Holiday rentals with a pool in Estero Bay

4.95 out of 5 average rating, 115 reviews

An outdoor heated pool is enclosed within a screened patio, featuring a spacious deck with lounge chairs. Lush greenery surrounds the area, and sunlight fills the space, creating an inviting atmosphere for relaxation. The pool's clear water reflects the bright blue sky above.

Home in Fort Myers

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

Superhost

A sparkling pool features a waterfall and is surrounded by palm trees. Lounge chairs are positioned around the pool area. In the background, views of the bay are visible under a clear blue sky, creating a serene vacation atmosphere.

4.92 out of 5 average rating, 203 reviews

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

4.88 out of 5 average rating, 123 reviews

The modern exterior of the home is highlighted by a manicured lawn and tropical landscaping, featuring palm trees and colorful shrubs. A paved driveway leads to a two-car garage, while a covered entrance invites guests into the villa.

Villa in Cape Coral

Heated Pool | Canal | Modern | New | Southern Exp.

Welcome to the brand new, absolutely stunning, Villa Southbreeze! This 3 bedroom, 2 bathroom vacation rental is fully furnished &equipped. Stunning high ceilings, huge 72" fireplace, office, laundry room all Samsung stainless-steel appliances, and much more. Out by the huge screened-in pool area you'll find a private electric heated pool, BBQ propane grill, several loungers, large table + chairs. The heated pool features two fountains and a shallow "beach area". Welcome to the villa Southbreeze!

4.93 out of 5 average rating, 15 reviews

Beachfront, Estero Beach Tennis 708A Weekly Stays

Wake up to stunning sunrises and wind down with breathtaking sunsets in this beautifully renovated beachfront condo on the South End of Ft Myers Beach. Enjoy luxury finishes throughout, including a sleek quartz countertop kitchen, modern appliances, and a spa-inspired walk-in shower. The layout and private balcony offer unbeatable ocean & bay views, making it the perfect escape for relaxation, comfort, and coastal elegance—all just steps from the sand. 708A is where your dream vacation starts!

A private balcony offers a panoramic view of the Gulf of Mexico at sunset. The tranquil water reflects hues of orange and pink, while the distant shoreline features a pier extending into the bay. Two lounge chairs are positioned to enhance the outdoor experience.

4.94 out of 5 average rating, 36 reviews

Beachfront Gulf View Lovers Key Beach Club #1002

Our beautiful 1BR condo is located directly on a private, white sugar-sand beach with beautiful Gulf and bay views from a private balcony. Modern amenities and new furnishings including two 40" flat screen smart TVs. Enjoy the heated swimming pool, gas grills and our uncrowded beach, with lovely Lovers Key State Park Beach connected directly to ours. Easy access to shopping, dining, and the trolley. There are many activities/watersports here or simply relax. Keep an eye out for the dolphins!

4.99 out of 5 average rating, 102 reviews

Home in Fort Myers

Comfy 3 BR-Group Friendly-Pool Access-BBQ-FGCU

Everything your group needs to be comfortable. 2 car garage w/remote Plenty of FREE on-site driveway parking for large work vehicles Logo vehicles ok Screened lanai w/ seating & BBQ Washer/Dryer Free, secure WiFi Smart TV in all rooms & 65” TV in Living Room Electric fireplace Well-stocked kitchen Keurig & Drip coffeemaker Toaster/crockpot Soap (laundry, dish, body, hair) Bathroom Items (Hair dryer, flat iron) Pantry items Community Pool Access 1 mile-Low fee Pack & Play & baby bath support

The open living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a vibrant area rug. The dining area includes a round table with four chairs, and a well-equipped kitchen is visible in the background.

5 out of 5 average rating, 15 reviews

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.

4.98 out of 5 average rating, 66 reviews

Home in Bonita Springs

Tropical Oasis: Stunning Pool Home in Bonita

Welcome to your tropical getaway in Bonita Springs! This stunning 4-bedroom, 2-bathroom home features a heated pool with a sunshelf, offering the perfect spot to soak up the Florida sunshine. Centrally located near the Coconut Point Mall, you'll have easy access to shopping, dining, and you're located just 15 minutes from Bonita Beach. Inside, enjoy spacious, coastal-themed living areas ideal for gatherings with family and friends. Your private oasis awaits—book now for a memorable stay!

4.99 out of 5 average rating, 150 reviews

An open living area features a cozy seating arrangement with a brown armchair and a textured ottoman. Wall art depicting botanical themes complements the neutral walls. A modern kitchen bar with three stools is visible, lending to the inviting and functional design of the space.

Home in Naples

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

4.93 out of 5 average rating, 157 reviews

A refreshing pool area features a heated pool surrounded by lounge chairs and a dining table. An inflatable pink flamingo floats in the water, while colorful umbrellas provide shade. Lush greenery frames the outdoor space, creating a bright and inviting atmosphere.

Home in Naples

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

4.97 out of 5 average rating, 114 reviews

A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.

Home in Bonita Springs

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to our peaceful Bonita Springs vacation retreat! This isn't just a rental, this is our home and we treat it as such: - You won't experience clean, you will experience immaculate. - You won't experience adequate, you will experience exceptional!. Come see for yourself...and you will be back year after year! Perfectly located between Naples, Fort Myers, numerous beaches & amazing shopping at every turn!