Roosevelt Roads Beach Holidays

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Top flight + Beach hotel deals in Roosevelt Roads

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

Ola Boutique Hotel

Condado
£998
per person
8 Dec - 15 Dec
found 1 day ago
Return direct flight included
London (LHR) to San Juan (SJU)
9/10 Wonderful! (957 reviews)
Maybe just stock the room refrigerators with some waters

Reviewed on 24 Sept 2026

Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

Zarzal
£1,190
per person
16 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LON) to San Juan (SJU)
9.2/10 Wonderful! (3,336 reviews)
Don Rafa Boutique Hotel & Residences

Don Rafa Boutique Hotel & Residences

Santurce
£1,020
per person
16 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LON) to San Juan (SJU)
9.4/10 Exceptional! (516 reviews)
We’ve been to Puerto Rico two times before and this was our first time staying in San Juan. We loved the overall vibe of the Don Rafa. It felt very upscale, but not pretentious. The views at breakfast and from the pool were phenomenal. The pool is definitely more of a lounging pool rather than for swimming, but it was exactly what we were looking for. Our room was very nice, big, and clean. The bathroom was very small, but clean and modern. We enjoyed having the refrigerator and walked around the corner to the grocery store to stock up on snacks and drinks. There are several restaurants just across the street, two of which are open 24/7. We enjoyed Pizza Birria, Los Pinos, and Puebla. I also highly recommend walking about 10 minutes to the rooftop restaurant, Eter. We took a Lyft to Escambron Beach and it was nice. However, we really preferred to purchase day passes for some of the local resorts if we wanted to spend a day at a pool that was right on the beach (highly recommend Fairmont El San Juan and Condado Ocean Club). We would definitely stay at Don Rafa again!

Reviewed on 23 Sept 2026

El Conquistador Resort

El Conquistador Resort

Cabezas
£1,401
per person
8 Dec - 15 Dec
found 1 day ago
Return direct flight included
London (LHR) to San Juan (SJU)
9/10 Wonderful! (3,559 reviews)
Las Casitas Village at El Conquistador

Las Casitas Village at El Conquistador

Cabezas
£1,492
per person
8 Dec - 15 Dec
found 1 day ago
Return direct flight included
London (LHR) to San Juan (SJU)
9.2/10 Wonderful! (276 reviews)
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5* Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II
£1,424
per person
16 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LON) to San Juan (SJU)
8.6/10 Excellent! (2,270 reviews)
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
£1,491
per person
16 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LON) to San Juan (SJU)
9.4/10 Exceptional! (1,837 reviews)
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Find your perfect Roosevelt Roads beach holiday

How can I book the best beach holidays in Roosevelt Roads?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Roosevelt Roads beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in Roosevelt Roads?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Roosevelt Roads beach holidays, which start from £998. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in Roosevelt Roads?

Enjoy out-of-season seclusion on a beach holiday to Roosevelt Roads during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in Roosevelt Roads with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a Roosevelt Roads beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute Roosevelt Roads beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in Roosevelt Roads. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find Roosevelt Roads beach holidays which are all inclusive?

A beach holiday to Roosevelt Roads is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a Roosevelt Roads beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a Roosevelt Roads beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Roosevelt Roads on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

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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. Flight-inclusive packages are ATOL protected.