Romantic Vacations in South Shore 2026

Photo by Brooke DeLane

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Flight and Romantic hotel deals in South Shore

Price found within the past 48 hours. Click for updated prices.

The Westin St. Francis San Francisco on Union Square

Union Square

CA $1,159

per person

Nov 4 - Nov 8

found 22 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Francisco (SFO)

8.8/10 Excellent! (2,273 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

CA $1,258

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Los Angeles (LAX)

8.2/10 Very good! (1,012 reviews)

Can't beat the location and the price. And fairly luxurious. Staff is extremely helpful.

Reviewed on Aug 31, 2026

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana

CA $4,329

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Los Angeles (LAX)

9.2/10 Wonderful! (525 reviews)

Perfect location. Very charming and intimate hotel! Lovely

Reviewed on Aug 24, 2026

1 Hotel San Francisco

Downtown San Francisco

CA $2,289

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Calgary (YYC) to San Francisco (SFO)

9.2/10 Wonderful! (593 reviews)

Great hotel! Great service! Great location!

Reviewed on Aug 30, 2026

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego

CA $2,184

per person

Oct 4 - Oct 11

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Diego (SAN)

9/10 Wonderful! (1,500 reviews)

Great staff, pillows and mattress should be updated

Reviewed on Sep 1, 2026

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5* Romantic holidays in South Shore

Price found within the past 48 hours. Click for updated prices.

1 Hotel San Francisco

Downtown San Francisco

CA $2,289

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Calgary (YYC) to San Francisco (SFO)

9.2/10 Wonderful! (593 reviews)

Great hotel! Great service! Great location!

Reviewed on Aug 30, 2026

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana

CA $4,329

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Los Angeles (LAX)

9.2/10 Wonderful! (525 reviews)

Perfect location. Very charming and intimate hotel! Lovely

Reviewed on Aug 24, 2026

The Huntington Hotel

Downtown San Francisco

CA $2,598

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Calgary (YYC) to San Francisco (SFO)

9.6/10 Exceptional! (33 reviews)

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3 Night Romantic holidays in South Shore

Price found within the past 48 hours. Click for updated prices.

The Westin St. Francis San Francisco on Union Square

Union Square

CA $984

per person

Nov 8 - Nov 11

found 22 hours ago

Roundtrip flight included

Edmonton (YEG) to San Francisco (SFO)

8.8/10 Excellent! (2,273 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

CA $1,098

per person

Oct 16 - Oct 19

found 1 hour ago

Roundtrip flight included

Edmonton (YEG) to Los Angeles (LAX)

8.2/10 Very good! (1,012 reviews)

Can't beat the location and the price. And fairly luxurious. Staff is extremely helpful.

Reviewed on Aug 31, 2026

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana

CA $2,097

per person

Oct 11 - Oct 14

found 7 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Los Angeles (LAX)

9.2/10 Wonderful! (525 reviews)

Perfect location. Very charming and intimate hotel! Lovely

Reviewed on Aug 24, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Shore

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4 Night Romantic holidays in South Shore

Price found within the past 48 hours. Click for updated prices.

The LEEF Hotel

Citrus Grove

CA $590

per person

Oct 10 - Oct 14

found 19 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Los Angeles (LAX)

8.6/10 Excellent! (817 reviews)

⚠️ FAIR WARNING to anyone thinking about booking a stay at THE LEEF. We stayed for 3 days/2 nights. The room itself is cute, and while there’s no microwave—which is inconvenient—it wasn’t a huge deal. What IS a huge deal is that we found TWO ROACHES in our room on the very first night. I reported it the following morning, but they weren’t able to provide us with a different room. Instead, I was offered cleaning services for that day and one day of free parking (aka $10) as compensation. However, on the next morning - checkout day, we found TWO MORE ROACHES. Four roaches during a two-night stay is absolutely unacceptable. A hotel should be able to provide guests with a clean, pest-free room, and the fact that we continued finding roaches after reporting the issue is disgusting. And don’t expect much when it comes to customer service. The so-called “lobby” is essentially just a screen with a virtual representative. When you have an actual issue that requires assistance, it makes the experience even more frustrating. I genuinely hope no one else has to worry about accidentally bringing roaches home with them after staying here. Do yourself a favor: if you value cleanliness and want a pest-free stay, DON’T STAY AT THE LEEF.

Reviewed on Aug 31, 2026

The Sofia Hotel

Downtown San Diego

CA $1,365

per person

Oct 8 - Oct 12

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Diego (SAN)

8.6/10 Excellent! (2,508 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

CA $1,011

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Los Angeles (LAX)

8.2/10 Very good! (1,012 reviews)

Can't beat the location and the price. And fairly luxurious. Staff is extremely helpful.

Reviewed on Aug 31, 2026

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What are some of the benefits of booking a romantic South Shore vacation?

When booking a romantic South Shore vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in California.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the South Shore destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in South Shore?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $590 and can enjoy savings of up to 34 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in South Shore?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout South Shore certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to South Shore.

Can I book a romantic South Shore vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your South Shore search.

Can I book a romantic trip to South Shore that is fully refundable?

Several romantic South Shore vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.