Holiday rentals with a pool in Redwood City

4.95 out of 5 average rating, 134 reviews

Condo in Mountain View

Spacious Top Floor Condo Retreat

Listen to the calming sounds of all the water features throughout the property from the secluded balcony. Inside, relax in 1000 square feet of upscale surroundings that include wood floors and high quality Tempur-Pedic king mattress. Later, head for the ground-floor pools and hot tub. 1000 sq ft of space on the top floor. Queen size adjustable firmness air mattress with clean beddings available upon request to be set up in the living room. You will be able to access the entire unit, 2 Swimming pools, and the hot tub. I will be available by text, phone or email throughout the stay. The quiet and beautiful setting is surrounded by trees. Within walking distance to CalTrain station, San Antonio shopping center, and Whole Foods, Trader Joe, movie theater plus numerous boutiques. Major tech companies located nearby include G00gle and Faceb00k. Stanford University is within a 10 minute drive. A short 5-10 minute walk to the Cal Train stop but the unit is not impacted by any train noise. The bus stop is conveniently around the corner to take you to Downtown Castro Street or Stanford University and beyond.

4.93 out of 5 average rating, 155 reviews

Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

4.99 out of 5 average rating, 330 reviews

Guesthouse in Woodside

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

4.89 out of 5 average rating, 161 reviews

Home in Mountain View

Little Poolside House near Downtown Mountain View!

Absolutely the best location in Mountain View, steps from Downtown! Situated near all the entertainment, nightlife & attractions this vibrant city has to offer. This beautifully furnished little poolside house is just minutes from the Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA Ames Center & more! Step outside for a stroll and explore local and international cuisine, wonderful farmers market and shopping! Perfect for family or friends, you will love this Bay Area getaway!

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 427 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

4.97 out of 5 average rating, 249 reviews

Guesthouse in Oakland

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Guest suite in Willow Glen

4.95 out of 5 average rating, 153 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and SJC. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry! You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom. Hot tub and Pool are a perfect way to relax and end the evening.

4.89 out of 5 average rating, 451 reviews

Guest suite in Woodside

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 581 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers.

Guesthouse in Walnut Creek

4.95 out of 5 average rating, 108 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 974 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

4.97 out of 5 average rating, 355 reviews

Home in Lafayette

Bay Area Refuge- Waterfall/Cave Spa, Amazing Views

Relax and rejuvenate your spirit in this uniquely designed home, situated under a canopy of sprawling oaks and with incredible panoramic views of Mt. Diablo and the valley, and multiple areas to relax. Hang out on the deck with a glass of wine, take a dip in the refreshing salt-water pool, or just melt away in our therapeutic cave spa. Centrally located in the East Bay just minutes from Lafayette, Walnut Creek, Berkeley and ~35 minutes from San Fran.

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Popular amenities for Redwood City rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 104 reviews

Home in Oakland

Summer-house/OASIS on quiet street in ROCKRIDGE!

MartinRating, 5 stars3 weeks ago

Very homey and welcoming. Family enjoyed celebrating time together in all spaces of the house, especially the back patio where our young child made believe on the well-designed pirate ship. Friendly, kind host. We walked to adorable Rockridge and BART many times. Highly recommended.

4.73 out of 5 average rating, 26 reviews

Home in San Mateo

Charming English Oasis

IgorRating, 5 stars3 months ago

I really enjoyed my two-week stay at Will's place! The apartment was clean and cozy, and the building appeared modern and new. I noticed a few reviews mentioning minor issues, but honestly, I had a great experience. The location is good – you can easily walk to a bakery, supermarket, and restaurants. Will was a great host, always available, friendly, and helpful with any questions. I recommend Will's place to anyone visiting the city – it's a great choice!

4.8 out of 5 average rating, 210 reviews

Home in Willow Glen

Beautiful Large 4BR Home with POOL

NatashaRating, 5 starstoday

Immaculately maintained, spacious property. Very relaxing. Close to all the necessary shops. Well equipped for families.

4.93 out of 5 average rating, 87 reviews

Home in Palo Alto

Large Home in Palo Alto w/Pool

AnilRating, 5 stars1 week ago

Very professional, courteous and excellent communication. The location and the accommodation excellent. The hosts also allowed us to check in very late and send us lots of good information around the areas.

4.89 out of 5 average rating, 54 reviews

Home in Menlo Park

Mission style, w. Pool, Hot tub, walk to downtown

SolinRating, 5 stars10 months ago

We stayed at Sara's while visiting family nearby, but her home felt like a vacation in itself. The backyard is magical - we spent a fair amount of time there, swimming, grilling/dining, reading/napping. The backyard (and its myriad diversions) even lured our tech-obsessed teenagers away from their devices for extended periods. Everything was well maintained, no detail overlooked. We also enjoyed the access to a peloton bike and workout equipment. The interior was clean, organized, stylish but comfortable. The sunroom and small courtyard off of the bedrooms were great for yoga or stealing a quiet moment with a cup of coffee or book. Sara was responsive and attentive. Instruction booklet was clear and helpful. The stay exceeded our expectations. We hope to be back.

4.86 out of 5 average rating, 125 reviews

Home in San Jose

Beautiful 3BD Home w/ Heated Pool and Fire Pit

BaharehRating, 5 stars15 months ago

The house was great for our family stay. Lots of space, all on one level, and beautiful outdoor space. We travelled with our kids and they had a great time in the pool :) Note there is extra cost if you want the pool to be heated. Thanks for a great stay!

4.81 out of 5 average rating, 324 reviews

Home in San Jose

Bay Area getaway w/ Pool + Heated Spa + EV charger

JessicaRating, 5 stars3 weeks ago

The house was awesome, having everything we needed, plus some nice extra touches like pool toys and snacks for a movie night. The only downside was that they had instructions to not turn the ac down past 72 and it was a very hot weekend, the house held onto a lot of heat and the bedrooms were very warm. The pool and spa were great, and we loved hanging out in the outdoor space.

4.96 out of 5 average rating, 113 reviews

Home in Ben Lomond

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

MaiaRating, 5 stars1 week ago

We live down in Santa Cruz and wanted to treat ourselves to a poolside weekend in the mountains (and this place did not disappoint!!). Would certainly stay again and appreciate how communicative the hosts were. As we get into summer we should have known better and brought our citronella candles because the mosquitos were out with a vengeance and forced us inside- so we recommend prepping for bugs if you want to stay poolside for sunset.

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Condo rentals with a pool

Condo in Downtown Oakland

4.92 out of 5 average rating, 293 reviews

Lakeside Retreat (w/ private parking)

DennisRating, 5 stars3 weeks ago

Very responsive and helpful host… would definitely go back and stay there when visiting the Bay Area again

Condo in Redwood Shores

5 out of 5 average rating, 18 reviews

Charming Luxury 2BR w/ Monitor and Adjustable desk

RachelRating, 5 stars3 months ago

The place is as described. It has everything you need. Communication with the host was great and very accommodating. I would definitely return and stay again!

4.94 out of 5 average rating, 31 reviews

Condo in Walnut Creek

Downtown Modern Living Condo!

ColleenRating, 5 stars1 day ago

It was a quiet complex and the house was a great option for us for a couple nights. Would stay again.

Condo in San Mateo

5 out of 5 average rating, 3 reviews

Luxury loft by the water

SondraRating, 5 stars1 month ago

As a solo female traveler in town for business, this place was great. Short distance to the office but had everything you needed for working remote. Loved the kitchen set up and had everything I needed to make breakfast and dinner. The bed was so comfortable, I didn’t want to leave! My rav4 fit well in the garage. The walking path outside was great for either starting your day or winding down.

Condo in Mission District

4.96 out of 5 average rating, 23 reviews

Art Deco Mission Flat

ShawnRating, 5 stars3 months ago

Lyssette’s lovely flat was exactly as described & very comfortable. It is in the heart of the mission district with so many restaurants & neat shops nearby. Highly recommended!

4.67 out of 5 average rating, 12 reviews

Condo in Grand Lake

Cozy condo by the lake

GaryRating, 5 stars1 month ago

The accommodations were nice and the area was quiet. It was a short walk to shops, restaurants, a movie theater and a 5 minute drive to a supermarket. It was a short walk to the lake which had a circumferential walking path. We particularly liked the locked parking garage. We will definitely come back.

4.94 out of 5 average rating, 17 reviews

Condo in San Jose

Charming 2 bedroom 2 story condo - No smoking

JesusRating, 5 stars2 weeks ago

We had a great stay at Mayela’s place! Communication was smooth and helpful she provided clear instructions and useful information before our arrival. The home was clean, comfortable. Parking instructions were very helpful as well. Overall, a great experience.