Holiday rentals with a pool in San Leon

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/HotTub, fenced in yard, patio table, chairs and umbrella. One block to Noah's Ark Restaurant, Pier and Public Boat Friday fireworks June/July

Agua Vista Waterfront Paradise/Hot Tub/Fish/Kayaks

Looking for a modern exquisitely decorated beach home where you can fish/kayak right off the back porch & enjoy sunrises/sunsets from multiple private decks? You've found it! Welcome to Agua Vista Waterfront Villa. Our gorgeous modern home features 3bedrooms up+Bonus 4th bedroom down +2.5baths w/ expansive living/kitchen space, Smart TV's in every room, Ping Pong, Kayaks provided for you, Fishing (w/ underwater lights), Shade, Games, 8 person Hot Tub, Fans on all porches and lots of beach toys!

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

Huge 6 Bedroom with Heated Pool, 85" TV, Game Room

Luxurious 5,200 foot home sits on a 0.5 acre lot and features 6 bedrooms, 4 bathrooms, game room, a hot tub and heated pool, an 85" TV with surround sound speakers, and a game room with foosball and a pool/ping pong/air hockey table! Please note the heated pool is at least $100 to use and the separate hot tub is $75. Charcoal grill, cornhole, giant jenga, connect 4, ping pong. Less than 10 miles from downtown and less than 5 miles from Hobby Airport. Ideal for large groups! 150+MBPS WiFi!

Gorgeous Clear Lake, Houston Home with Pool

Outstanding Clear Lake City, Houston home only 5 minutes to NASA JSC and 20 minutes to Downtown Houston, or the Kemah Boardwalk! The home features a huge pool and spa with a 4 ton rock waterfall! The pool and spa can be heated. Spa is free to heat but we charge to heat the pool in winter. The back patio is exceptionally large and perfect for enjoying the outdoor space day and night. What can I say about the house itself? This was our own home for 18 years and we made it delightful!

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!

Boardwalk POOL Home w optional Heated pool

This spacious wheelchair friendly home, with a backyard POOL, is conveniently located on one of the best streets in Kemah! Enjoy being just a stone's throw away from the famous Boardwalk and all its attractions, while also being somewhere quiet, relaxing and comfortable for your stay. Uber, taxi, and bicycles are all available for transportation. Enjoy some rest and relaxation with your family here at this convenient and accessible STRICT NO PET POLICY maximum 8 adults

Coastal Breeze: Pool, Firepit & 4 Bathrooms!

Beautifully restored by the “Restoring Galveston” TV show team, this cottage ranks at the top of Airbnb’s list. It’s also been on the cover of Houston House & Home magazine as well as featured on the Galveston Historic Homes Tour. It has earned these honors by blending timeless heritage with tasteful, modern design. Built in 1871, the home is a testament to the island’s rich past and resilience—having weathered the Storm of 1900 and enduring generations of change.

Staycation Home w/Pool/Arcade/Style & Great Area

As of Summer 2026 the pool is open. Spa is not heated. Extremely comfortable home feel. Located on a very relaxed street. 3-bedrooms, 2-bathrooms, 6-beds open concept home allows for easy living in a very comfortable home that is perfect for a getaway for two, or even two whole families. Streaming TVs and memory foam mattresses in every room. Houston- 29 min to downtown NASA- 20 min Galveston- 1 hour Baybrook Mall- 25 min 5 minutes from many restaurants

Beach Themed Oasis with Jacuzzi/Pool

Bring the whole family along to this spacious home to enjoy all to yourselves. Swim in the massive pool or lay in the jacuzzi by the 2 pergolas. Cook BBQ outside on the grill (no backyard neighbors). 1 King size master bedroom, 1 full size bedroom and 1 full size kids bedroom, convertible sofa and air mattress provided upon request. Gorgeous kitchen area and massive family room with blazing fast cable/ internet and streaming services.

Fishing Heaven! Walk 1 min to pier & catch dinner!

Great water views of the Galveston Bay are easily seen! Early morning or late evening fishing off the pier is an enjoyable experience. Prefer swimming then check out the pool all while looking at the ships sailing along the Ship Channel which is a great sight! The pelicans flying overhead lets you know you are at the heart of the Galveston coastline! Experience an amazing coastal sight!

The Oasis Guest House | Pool • Near Beach

Slow down, unpack, and enjoy island time at The Oasis Guest House. Perfect for couples and young families, this cozy retreat offers a private deck, full kitchen, baby gear, toys, books, and shared access to our splash pool and beach equipment. Less than a mile from the beach, it's a place where parents can finally relax while kids stay happily entertained.