Holiday rentals with a pool in San Leon

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Top-rated rentals with a pool in San Leon

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

An aerial view of a beach house revealing a spacious layout. The home features multiple levels with a balcony overlooking a private pool and adjacent spa. Surrounding the pool, seating areas provide views of the tranquil canal and neighboring residences.

Home in Jamaica Beach

4.96 out of 5 average rating, 130 reviews

Pelican Lookout | Heated Pool, Spa, Fire Pit, Bar

Welcome to your waterfront escape in Jamaica Beach with beautiful panoramic views on the main canal. Ideal for families & friends looking to relax & enjoy coastal living! This spacious canal-front home combines comfort, fun amenities & easy beach access: - Sleeps 12 | 4 bedrooms | 9 beds | 3 baths - Private heated pool & hot tub with marble deck - Fire pit & Outdoor bar w/HDTV - BBQ Grill - Boat slip, kayak & beach supplies - Arcade & board games - Stocked kitchen - Outdoor dining area on deck

Top guest favourite

A charming cottage is showcased with a vibrant teal exterior. Sturdy steps lead to a welcoming porch, which overlooks a fenced pool area surrounded by green grass and trees. Sunlight bathes the property, enhancing its inviting appearance.

Home in San Leon

4.96 out of 5 average rating, 285 reviews

Lakeview Cottage (pool, fishing pier, lake)

Perfect for a small family vacation. This 3 bedroom cottage is larger inside than it may appear. The pool, the fishing pier on the lake, and the beautiful views are its best amenities. The porch is the ideal place to just relax and unwind while you take in the gorgeous view of the lake. The pool area is only a few steps from the porch. The living room offers plenty of space with comfortable furniture. Full kitchen with all appliances. Sleeps about 6. Pull out bed in livingroom. Pets ok limit 2

Guest favourite

An aerial view of the Breezeway unit is displayed, showcasing its green exterior. The cottage is raised on pillars, surrounded by a spacious driveway. A private pool with lounge chairs is visible beside the house, set against a backdrop of lush greenery and open fields.

Home in Pirates Beach

4.85 out of 5 average rating, 128 reviews

Breezeway: Pool/Spa Heating on Request

Welcome to Blue Haven Cottages! NEW property with 2 units - separate rentals (Breezeway & Bayview) & private pool in a serene neighborhood. Behind the Galveston State Park and overlooks the Bay. Each unit offers a cozy, spacious/modern interior, 65 in smart TV, fully stocked kitchens, dining areas, 2 bedrooms with king beds, 50 in smart TVs, bunk beds 2 twin, 2 ½ bath and stunning views from various deck. Beach access #16, dine at Waterman’s, Dollar General (basics/meds), a 2-3 min drive.

Guest favourite

A cozy living area is shown, featuring a green sofa with colorful pillows. A small table sits in front, adorned with a decorative arrangement. Light filters through sheer curtains, illuminating the space. A balcony door opens to a view of the outdoor area.

Apartment in Galveston

4.93 out of 5 average rating, 106 reviews

Beach Happy Retreat Seawall 2 Pools HotTubs Perfec

Perfect Island Escape! We are centrally located right on the seawall! Enjoy covered parking, 2 pools, 2 hot tubs, a fitness center and outdoor BBQ grill for steaks & goodies! You also have 2 Certified Tourism Ambassadors for Galveston, to answer questions & assist with any concerns or needs while staying in our beautiful retreat. CRUISE SHIP PARKING AVAILABLE INCLUDED WITH STAY FREE FOR 7 DAYS! ONLY $35 FOR AN ADDITIONAL 7 DAYS!! Gated lot, overnight security & cameras. Good neighborhood.

Guest favourite

An open living area features a dining table for four and a comfortable black sofa accented with decorative cushions. The space is illuminated by pendant lights, with wooden flooring and area rugs enhancing the warmth. A mirror reflects the room’s inviting design.

Home in Seabrook

4.9 out of 5 average rating, 104 reviews

Dog Friendly Cottage w/ pool, great for work/play!

This cute cottage is conveniently located in Seabrook - halfway between Houston & Galveston. This sits on a property that is a little over a 1/2 acre. The main house is next door. The cottage is completely detached & has its own small fenced backyard. Feel like you're in the country yet just a hop & a skip to the highway. Guests love being so close to amazing restaurants, bars, live music, shops & beaches! It's a great "homebase" for your vacation or if you're traveling for work!

Top guest favourite

A wooden walkway leads toward a light blue house, framed by lush greenery. A sign is mounted on a post, humorously stating that the staff is accustomed to inquiries. A red umbrella is visible, providing shade to the area.

Guest house in Clear Lake Shores

4.94 out of 5 average rating, 493 reviews

Private bungalow in paradise.

My husband and I enjoy meeting new people and sharing the treasures in the Galveston Bay Area. We are located just 1.5 miles from the Kemah Boardwalk, minutes from NASA/Space Center, & halfway between Galveston and Downtown Houston. You’ll love our place because of the quaint island setting, great for sunrise and sunsets. Come watch the boats passing and relax on island time, all while being respectful of our neighbors. We have a pool (not heated) and hot tub. No parties allowed.

Guest favourite

The living room features a fireplace set within a stone wall, flanked by potted plants. Comfortable seating is arranged around a wooden coffee table, which holds a cozy blanket and decorative items. A television above the fireplace displays a serene landscape.

Home in Kemah

4.93 out of 5 average rating, 124 reviews

Kemah's Bayfront Getaway with Pool

Beautifully decorated, waterfront bay house featuring a spacious deck, 200ft pier for fishing/boating, and a swimming pool. This 3-story home is within walking distance of Kemah's top restaurants and bars. This spacious home features four bedrooms & four full baths. Whether you want to sit on the balcony and enjoy the sunrise with a cup of coffee, take a dive in the swimming pool or go fishing in the pier, it is the perfect getaway for families to relax and spend quality time!

Guest favourite

An outdoor deck is illuminated by purple lighting, featuring a gas firepit surrounded by comfortable seating. A Weber gas grill is visible nearby, and a spiral staircase leads to an upper level, providing expansive views of the night sky and distant shoreline.

Home in Bacliff

4.97 out of 5 average rating, 104 reviews

Retro Diner Heated Pool/HotTub Deck

Authentic Starlight Diner Converted to a Bayside Bungalow on Galveston Bay! This Charming and Unique Waterfront Property has Panoramic views of Galveston Bay from Kemah to Red Fish Island. The deck has comfy sectional/chairs, gas firepit, Weber gas grill. Two Bathrooms and Huge Master Shower, Two Bedrooms with darkening curtains. The Yard with Heated Pool/Hot Tub, fenced in yard, patio table, chairs and umbrella. One block to Noah's Ark Restaurant, Pier and Public Boat

Top guest favourite

A charming casita with a covered porch is framed by vibrant greenery and colorful flowers. Blue adirondack chairs provide a cozy seating area. A pathway leads to the entrance, enhancing the inviting outdoor space surrounded by lush landscaping.

Guest house in Bacliff

4.98 out of 5 average rating, 131 reviews

Sunny View Cabin: Clothing Optional Heated Pool

Come enjoy our backyard oasis. We are adults only shared backyard, clothing optional where you can enjoy our outside palapa with full kitchen, cooktop, fridge, commercial ice maker, Weber gas grill, gas fireplace, fire pit with seating area, 12 person heated spa, optional heated pool, outdoor bathroom with hot/cold shower. Inside your private casita with full kitchen, queen pillow top mattress. There is only 2 guests in your unit. No additional guests allowed.

Top guest favourite

A light-colored horse stands in a grassy area beside a winding creek, with a scenic barn and a white farmhouse visible in the background. Tall trees provide a natural border, enhancing the serene rural landscape.

Barn in Santa Fe

4.9 out of 5 average rating, 469 reviews

The Loft at Green Gables

Cozy barn apartment on a lovely small farm, secluded and quiet in the country. Located halfway between downtown Houston and the Galveston beaches, it's just a few minutes to lots of shopping and restaurants, with Kemah Boardwalk and Nasa Space Center a short drive away. Winding creek through the property, with chickens and two horses grazing in the pasture. Lots of sheep, pigs, and donkeys next door. Property has private swimming pool for your enjoyment.

Guest favourite

A houseboat is docked at the marina, featuring a blue and white exterior. The two-level structure is equipped with a top deck for views. Surrounding water reflects the clear sky, creating a serene atmosphere. Nearby boats are visible, adding to the maritime setting.

Houseboat in Kemah

4.92 out of 5 average rating, 424 reviews

Feel the Harmony with our Cozy Houseboat

Ready to relax on the water, pictures speak for themself. Our houseboat serves as bed and bath and don't leave on dock. Our kitchen offers great equipment to feel just like home. You will be staying very close to all the attractions that kemah is famous for and only 15 min from Space Center and 45 mins to Galveston with so many great restaurant to eat around. Our location is very peaceful with a great fishing dock just steps away.

Guest favourite

This collage showcases the Lodge on Galveston Bay, featuring a glistening pool surrounded by a spacious patio, a bright living area with large windows offering bay views, a modern kitchen with sleek appliances, and cozy sleeping arrangements in a well-lit bedroom.

Home in San Leon

4.92 out of 5 average rating, 104 reviews

Gorgeous Lodge w/Heated Pool + Pier

Welcome to our Gorgeous waterfront Lodge. ▪ Fully equipped kitchen. ▪ Sleeps 20 Guest max. ▪ Main bedrooms with Roku TVs, private bathrooms, and Galveston Bay views. ▪ bunk room with TV & full bathroom for the kids. ▪ Peaceful & Safe. ▪15 minutes to Kemah Boardwalk, 30 minutes to Galveston, & 5 minutes to 5-star restaurants Perfect for family reunions, weddings, & corporate events when combined with neighboring homes.