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Vacation rentals with a pool in Estero Island

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Estero Island rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favorite
A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.
Home in Cape Coral
5 out of 5 average rating, 58 reviews

Coastal Cowgirl - Heated Pool

Top guest favorite
An inviting screened-in patio features a large heated swimming pool surrounded by lounge chairs. Sculptures adorn the sides of the pool, and lush greenery is visible through the expansive windows, offering tranquil views of the outdoors and tranquil ambiance.
Home in Cape Coral
5 out of 5 average rating, 74 reviews

Luxe Riverfront Retreat~Pool~Spa~Bar~Tropical Yard

Top guest favorite
The inviting outdoor area features a heated saltwater pool with an integrated whirlpool. Sun loungers are positioned nearby, and the screened enclosure creates a bright, airy atmosphere with views of the surrounding greenery and water.
Home in Cape Coral
5 out of 5 average rating, 17 reviews

Brandnew Villa - pool & spa at canal south facing

Top guest favorite
A clear blue pool is surrounded by a spacious paved deck, featuring several lounge chairs for relaxation. A covered outdoor area provides additional seating and shade. Lush green grass borders the pool, with palm trees visible in the background under a bright sky.
Home in Fort Myers Beach
4.93 out of 5 average rating, 113 reviews

Escape to your Happy Place-pool, 6 bed 2 1/2 bath

Superhost
Home in Fort Myers Beach
5 out of 5 average rating, 4 reviews

Ocean Pearl - Steps from the Beach

Guest favorite
The screened-in pool area features a sparkling swimming pool surrounded by a spacious deck. Natural light filters through the mesh enclosure, reflecting off the water. Outdoor seating is provided by a small table and chairs, with trees framing the serene backdrop.
Home in Fort Myers
4.95 out of 5 average rating, 126 reviews

Waterfront Home w/ Pool. Minutes to Sanibel

Top guest favorite
Home in Cape Coral
5 out of 5 average rating, 11 reviews

Riverfront Riviera Outdoor TV's/Hotub/Tanning Deck

Guest favorite
Home in Cape Coral
5 out of 5 average rating, 5 reviews

Cape Escape | Hot Tub | Heated Pool | Game Room

Condo rentals with a pool

Top guest favorite
A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.
Condo in Sanibel
4.89 out of 5 average rating, 249 reviews

Rare walkout condo on Sanibel beach-Fully Restored

Guest favorite
A panoramic view showcases a sparkling heated swimming pool surrounded by lounge chairs, with the beach and Gulf of Mexico visible in the background. Soft waves lap at the shore while sunbathers can be seen enjoying the sandy area. Lush palm trees frame the scene.
Condo in Fort Myers Beach
4.88 out of 5 average rating, 96 reviews

Beachfront fully equipped apartment

Guest favorite
A comfortable living area is highlighted by a deep red sofa adorned with decorative pillows. A glass coffee table sits on a large area rug, while a view of the water is framed by sliding glass doors that open to a private outdoor space.
Condo in Fort Myers Beach
4.9 out of 5 average rating, 79 reviews

Boutique condo on the bay, short walk to the beach

Guest favorite
A spacious living area is presented, featuring a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table sits at the center, complemented by a neutral area rug. Large sliding glass doors lead to a balcony, offering views of the greenery.
Condo in Fort Myers Beach
5 out of 5 average rating, 17 reviews

Waterfront Condo | Huge Pool & Across from Beach

Guest favorite
A wide, sandy beach stretches along the shoreline, showcasing smooth white sands leading to gentle waves. In the background, several multi-story buildings are visible, contrasting with the natural landscape. A pathway and a distant individual walking along the beach add to the serene atmosphere.
Condo in Fort Myers Beach
4.89 out of 5 average rating, 56 reviews

Direct BEACH FRONT - Ocean Views

Superhost
A cozy living room features a light-colored sofa and an accent chair, complemented by a wooden coffee table. A piece of coastal artwork decorates the wall. The space opens to large sliding glass doors, providing views of the ocean and access to an outdoor balcony.
Condo in Fort Myers Beach
5 out of 5 average rating, 4 reviews

Seaside Resort Unit 309-Fall Special

Guest favorite
A tall, modern building is seen from above, surrounded by water and lush greenery. The calm waters reflect the clouds in the clear blue sky. A small parking area and palm trees are visible in the foreground, highlighting the property's serene waterfront location.
Condo in Fort Myers Beach
4.94 out of 5 average rating, 52 reviews

Lover's Key Resort Unit #807

Superhost
The exterior of a tall, six-story building is visible, situated along the waterfront. The structure features multiple balconies overlooking the bay, surrounded by lush greenery. Calm waters reflect the clear sky, while distant land can be seen along the horizon.
Condo in Fort Myers Beach
4.81 out of 5 average rating, 21 reviews

BONITA SPRINGS / FORT MYERS WATERFRONT 1 BEDROOM

Other vacation rentals with a pool

Superhost
The image captures a panoramic view of Lovers Key Resort, showcasing the tranquil Estero Bay and the Gulf of Mexico. Towering palm trees frame the scene, while a pier extends into the water. Two adjacent resort buildings are visible, highlighting a coastal setting.
Apartment in Fort Myers Beach
4.8 out of 5 average rating, 15 reviews

Lovers Key Resort, Ft Myers Beach

Top guest favorite
A spacious outdoor seating area features a circular conversation arrangement with cushions and pillows. The view showcases a private pool illuminated by the evening sky's vibrant colors, with palm trees in the background, creating a serene ambiance.
Villa in Cape Coral
5 out of 5 average rating, 10 reviews

Vry Private 3/3 Ensuite + Pool/Spa Outdoor Kitchen

Top guest favorite
An aerial view showcases the vacation rental's proximity to Fort Myers Beach, with a clear line of sight to the coastline. Surrounding buildings and facilities are visible, alongside the canal leading to the home. The vibrant blue ocean completes the serene landscape.
Home in Fort Myers Beach
4.97 out of 5 average rating, 35 reviews

Modern 3BR House @ Estero Island

Superhost
Home in Lehigh Acres
5 out of 5 average rating, 4 reviews

Lehigh Eden| Pool & Jacuzzi | Games | Pet friendly

Top guest favorite
A private heated saltwater pool is surrounded by a paved patio featuring colorful pool floats. A spacious bed is adorned with a light blue quilt, placed against a beach-themed mural. The lower right image displays a brightly colored house exterior with a large garage beneath.
Home in Fort Myers Beach
5 out of 5 average rating, 15 reviews

Oceanview Oasis: Private Heated Pool & Local Art

Guest favorite
An open living area is displayed, featuring a light-colored sectional sofa positioned near a wooden entertainment center, equipped with a large television. Bar stools line the counter of a modern kitchen visible in the background, adorned with tasteful decor and soft lighting.
Apartment in Fort Myers Beach
4.95 out of 5 average rating, 22 reviews

Sunset Serenity Condo

Top guest favorite
A serene outdoor space is showcased, featuring a sparkling pool surrounded by a stone patio. Several lounge chairs are positioned under a large umbrella, with palm trees swaying gently in the background. A hammock can be seen nearby, adding to the relaxing atmosphere.
Home in Fort Myers Beach
4.93 out of 5 average rating, 28 reviews

2 BR home w/ private pool, 2 min walk to beach

Guest favorite
Apartment in Fort Myers Beach
4.93 out of 5 average rating, 28 reviews

Sun & Fun | Beach Front Condo, Pool, Tennis

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