Villa holiday rentals in San Diego Bay

4.92 out of 5 average rating, 12 reviews

The Kensington Canyon Estate

Beautifully restored Kensington retreat blending historic charm with modern luxury. Approaching its 100th anniversary, this home has undergone a complete $250,000 renovation, offering the comforts of brand-new construction while preserving its timeless character. Located on quiet Hart Drive in one of San Diego’s most beloved historic neighborhoods, guests can enjoy tree-lined streets and walkable cafés, restaurants, and shops—just minutes from beaches, Balboa Park, downtown, and top attractions.

A private rooftop deck features a hot tub, seating area with lounge chairs, and a dining table. Scenic views of the harbor and city skyline are visible at dusk, with warm lights creating a peaceful ambiance. The space is surrounded by terracotta roof tiles.

4.94 out of 5 average rating, 117 reviews

☆🏘 Breathtaking 180º Views 🏝Hot Tub🏝 5☆ Reviews

🏝Welcome to the Harbor View Villa! 🏘A 3,500sqft villa with 6 bedrooms, 4 bathrooms and a 800 sqft walk-out deck. Complete with private rooftop hot tub, backyard, outdoor & indoor living.  With 180º private day & night views from almost anywhere in the house! Make yourself at home in our Mission-Style Villa with stunning views of the boats in the Harbor, Downtown lights, and Coronado Island! 🗺Ideal for kids Perfect for MCRD & PLNU graduations (5min). Ask about early checkin / late checkout

A spacious outdoor area features a clear swimming pool surrounded by a patio. Lush palm trees and other greenery create a private atmosphere. A gazebo and dining seating area are visible, providing a relaxing space for gatherings and leisure.

4.92 out of 5 average rating, 107 reviews

5-bed Paradise Villa Pool, hot-tub massage chair

*EV charging available Welcome to Casa Cerro-my incredible chic high-tech modern villa in San Diego! This stylish place to stay is perfect for families and group trips. Its open and airy layout can accommodate up to 14 people. This completely remodeled home is furnished with all the luxuries of home and more that is powered by an iPad for you to use. I love technology. But don't worry you don't have to use it to power up the house, everything has traditional switches/remotes if you choose.

4.96 out of 5 average rating, 158 reviews

Villa in El Cajon

@Fantastic villa, giant pool, guest house, golf !

This unique fantastic villa with a separate pool house sitting on 1 acre with a spacious living space with large windows. Main house has 4 bedrooms with 2 baths, and a guest house has 1 bedroom with 1 bath. +8 car parking, nice privacy and a fantastic view! Brand new giant size SALT pool with huge size jacuzzi, pool toys, golf zone, a huge grass event field, game field, pool table, foosball, ping pong, Nitendo,2 fire pits and more! Truly one-of-a-kind property don’t miss out! ToT:COSD-00749

Luxe

4.93 out of 5 average rating, 15 reviews

Villa Bermuda Beach

NEW CEMENT STEPS TO SANDY BEACH BELOW--(City installed in May 2024). Safe accessible steps to the sandy beach below Villa Bermuda Beach. The steps are located one property north of Villa Bermuda Beach. Contemporary Oceanfront Retreat Overlooking Pacific Ocean and Accessible White Sand Beach Below the Oceanfront Deck Exceptions to the general "No Pets Rule" can be requested. There is a non-refundable pet fee of $495 per pet that is charged on each pet that is brought to Villa Bermuda Beach.

A living area features a mix of seating options, including a blue sofa and a red chair. A wooden coffee table is positioned centrally. Floor-to-ceiling shelving holds a variety of books and DVDs. A dining area is visible, accompanied by natural light from nearby windows.

4.98 out of 5 average rating, 102 reviews

Hidden Villa with Beautiful Furnished Garden Patio

Close to everything, quiet and private. This beautiful 2 Bd Villa seems to be loved by all who stay here. The outdoor private patio feels like your in the forest. Gorgeous custom bath with large marble shower. Full size laundry. Great entertainment system, Roku, Amazon Prime. The home has open beam ceilings, lots of light and a fabulous patio fully furnished for guests, outdoor dining and barbecuing. The home is private, fenced, furry friends are welcome. 2 gig internet w/high speed router

An aerial view showcases the Spanish-style estate, highlighting its beautiful architecture with terracotta roof tiles and vibrant landscaping. The outdoor patio features a comfortable seating area under a pergola, adorned with market lights, creating an inviting ambiance for outdoor gatherings.

4.8 out of 5 average rating, 5 reviews

Panoramic Ocean Views - Spanish Villa+Rooftop Spa

Welcome to this exquisite Spanish-style estate perched high above La Jolla in the prestigious La Jolla Alta enclave. This lavish 4-bedroom, 4.5-bath residence offers an unrivaled blend of elegance and harmony, with sweeping panoramic ocean and sunset views framed by lush tropical landscaping. With its luxurious amenities and versatile living spaces, it provides the perfect setting for creating cherished memories, strengthening bonds, and facilitating productive discussions among colleagues.

Villa in El Cajon

5 out of 5 average rating, 3 reviews

East County San Diego Dream Luxury Estate

Welcome to this luxurious experience in the heart of Granite Hills. This spacious Rancho Santa Fe-inspired estate combines timeless design with modern comfort. With 4 bedrooms, 4 bathrooms, and thoughtful custom features throughout. High ceilings, natural stone flooring and a gourmet kitchen that brings everyone together. Views of city lights and mountain sunsets. A dreamy outdoor space with an oversized hot tub, sparkling pool, built in BBQ and cozy fire pit with views from room to room.

Superhost

An aerial view captures a spacious villa with a unique architectural design. Surrounding the home, a well-maintained outdoor area includes a private swimming pool, lounge seating, and landscaped gardens. Solar panels are visible on the roof, emphasizing sustainable features in this inviting retreat.

4.8 out of 5 average rating, 56 reviews

Historic Villa, Blocks from the Beach, Ocean Views

Built in 1923, this beach town retreat has tons of old world charm with all the modern amenities. Only 6 blocks to the beach, you couldn't ask for a better location. Dog Beach, Sunset Cliffs and some of the best bars, restaurants and vintage shops in all of San Diego are just outside your doorstep. ☞ 3 Bedrooms ☞ Private Hot Tub ☞ Private Swimming Pool ☞ Outdoor Dining ☞ Ocean Views (perfect for sunset cocktails) ☞ Outdoor Grill ☞ Bikes to enjoy the neighborhood ☞ Chef's Kitchen

4.88 out of 5 average rating, 200 reviews

The outdoor space features a private pool surrounded by lounge chairs. A small jacuzzi is visible beside the pool. A covered seating area is present, with a table and chairs for relaxation. String lights are draped overhead, enhancing the garden atmosphere.

Villa in Tijuana

Beach House

Villa vacacional de lujo localizada en la hermosa Playas de Tijuana, a tan solo 15 min de la frontera con San Diego y 20 min de Rosarito. Check in 1 pm Check out 11 am Límite de huéspedes 13, puedes reservar hasta 16 huéspedes pero sería tu decisión dónde y cómo dormirían. Invitados extras $10 usd Cuidamos y respetamos la noche de nuestros vecinos, por lo tanto si recibimos quejas de ruido serás multado con $200 usd o te retiras del alojamiento Hora de silencio comienza 11pm

4.9 out of 5 average rating, 288 reviews

A serene outdoor area features a hot tub surrounded by stone elements and a waterfall feature. Sunlight filters through the overhead pergola, creating a play of light and shadow. Lush greenery and a glimpse of a spacious pool can be seen in the background.

Villa in La Mesa

Private Villa: Pool, Slide & Hot Tub

Summary: * Spacious: 5,000 SF indoor living space & 10,000+ SF outdoor living space * Fantastic Pool: Complete with waterslide, cave /grotto & multiple fountains / waterfalls * Relaxing Hot Tub: 5 hours of free heating daily from 5pm-10pm * Event Policy: No weddings, events, or parties with 16 or more guests * Accommodates: This home can accommodate up to 16 guests /see “more things to note" for more info on beds/air mattresses

The open kitchen and living area feature modern finishes and large windows, providing views of the water. A dining table is set with plates and glasses, while colorful flowers add a touch of decor. Comfortable seating is arranged for relaxation.