South Shore Romantic Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Brooke DeLane
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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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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

The Westin St. Francis San Francisco on Union Square

Union Square
CA $1,203
per person
Nov 8 - Nov 12
found 13 hours ago
Roundtrip flight included
Edmonton (YEG) to San Francisco (SFO)
8.8/10 Excellent! (2,267 reviews)
Wonderful

Reviewed on Aug 16, 2026

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego
CA $1,367
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
9/10 Wonderful! (1,466 reviews)
Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana
CA $2,875
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Los Angeles (LAX)
9.2/10 Wonderful! (520 reviews)
It’s a nice hotel but it’s definitely not worth the price of the room. The pool is super tiny and will be overtaken by children. The only restaurant onsite is priced extremely high and the service is terrible; slow, expect to sit there for 2.5 hours. I also ordered a $130 bottle of prosecco but paid around $193 for it due to charges of having it delivered to my room, (from the restaurant onsite?) Paying $63 extra for having delivered what you order from the menu in your room is absurd. I have stayed at the Four Seasons, The Ritz, etc. and none have been as desperately money hungry as Oceana. I paid about $1050 for the one night and honestly people could get a way better experience for that price anywhere else. Expect to get charged for breathing at Oceana. I wouldn’t go back there.

Reviewed on Aug 16, 2026

Shore House at The Del, LXR Hotels & Resorts

Shore House at The Del, LXR Hotels & Resorts

Historic Downtown Coronado
CA $2,744
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
9.2/10 Wonderful! (169 reviews)
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5* Romantic holidays in South Shore

Price found within the past 48 hours. Click for updated prices.
1 Hotel West Hollywood

1 Hotel West Hollywood

West Hollywood
CA $1,964
per person
Oct 25 - Oct 29
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Los Angeles (LAX)
8.8/10 Excellent! (1,003 reviews)
Great hotel one of the best in LA. Pool is amazing

Reviewed on Aug 17, 2026

Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana
CA $2,875
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Los Angeles (LAX)
9.2/10 Wonderful! (520 reviews)
It’s a nice hotel but it’s definitely not worth the price of the room. The pool is super tiny and will be overtaken by children. The only restaurant onsite is priced extremely high and the service is terrible; slow, expect to sit there for 2.5 hours. I also ordered a $130 bottle of prosecco but paid around $193 for it due to charges of having it delivered to my room, (from the restaurant onsite?) Paying $63 extra for having delivered what you order from the menu in your room is absurd. I have stayed at the Four Seasons, The Ritz, etc. and none have been as desperately money hungry as Oceana. I paid about $1050 for the one night and honestly people could get a way better experience for that price anywhere else. Expect to get charged for breathing at Oceana. I wouldn’t go back there.

Reviewed on Aug 16, 2026

Shore House at The Del, LXR Hotels & Resorts

Shore House at The Del, LXR Hotels & Resorts

Historic Downtown Coronado
CA $2,744
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
9.2/10 Wonderful! (169 reviews)
Don't see what you're looking for?
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3 Night Romantic holidays in South Shore

Price found within the past 48 hours. Click for updated prices.
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego
CA $910
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
9/10 Wonderful! (1,466 reviews)
Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

Wilshire Montana
CA $2,494
per person
Oct 22 - Oct 25
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Los Angeles (LAX)
9.2/10 Wonderful! (520 reviews)
It’s a nice hotel but it’s definitely not worth the price of the room. The pool is super tiny and will be overtaken by children. The only restaurant onsite is priced extremely high and the service is terrible; slow, expect to sit there for 2.5 hours. I also ordered a $130 bottle of prosecco but paid around $193 for it due to charges of having it delivered to my room, (from the restaurant onsite?) Paying $63 extra for having delivered what you order from the menu in your room is absurd. I have stayed at the Four Seasons, The Ritz, etc. and none have been as desperately money hungry as Oceana. I paid about $1050 for the one night and honestly people could get a way better experience for that price anywhere else. Expect to get charged for breathing at Oceana. I wouldn’t go back there.

Reviewed on Aug 16, 2026

Don't see what you're looking for?
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4 Night Romantic holidays in South Shore

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

Encore Inn Inglewood

Lockhaven
CA $520
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Los Angeles (LAX)
6.6/10 (196 reviews)
It said no smoking but smelt like weed

Reviewed on Aug 16, 2026

The Sofia Hotel

The Sofia Hotel

Downtown San Diego
CA $1,272
per person
Oct 8 - Oct 12
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
8.6/10 Excellent! (2,462 reviews)
Don't see what you're looking for?
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Plan unforgettable romantic South Shore vacations

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 $520 and can enjoy savings of up to 42 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.