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
£925
per person
19 Oct - 26 Oct
found 16 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
9/10 Wonderful! (919 reviews)
Aire de O:live

Aire de O:live

Isla Verde
£1,388
per person
15 Sept - 22 Sept
just found
Return direct flight included
London (LON) to San Juan (SJU)
9.2/10 Wonderful! (725 reviews)
Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
£1,371
per person
26 Sept - 3 Oct
found 23 hours ago
Return flight included
Manchester (MAN) to San Juan (SJU)
8.8/10 Excellent! (710 reviews)
I really enjoyed my stay, and the staff made us feel welcomed.

Reviewed on 7 Aug 2026

Wyndham Palmas Beach and Golf Boutique Resort

Wyndham Palmas Beach and Golf Boutique Resort

£1,376
per person
23 Oct - 30 Oct
found 1 day ago
Return flight included
London (LON) to San Juan (SJU)
8.4/10 Very good! (825 reviews)
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
£1,469
per person
15 Sept - 22 Sept
just found
Return direct flight included
London (LON) to San Juan (SJU)
9.4/10 Exceptional! (1,795 reviews)
Good: - Nice selection of pools, they have a nice infinity hot tub on one side of the hotel, as well as a family pool. The other side has an adult only pool and hot tub. THOUGH the adult side was never super clean. Bad: - Rooms were jank, everything half worked and it looked like several fixes were just cheap patch jobs. Appliances and electronics didn’t work turn on half the time. My ocean view room I booked faced a wall and patio area. - Staff will treat you different if you aren’t some rich businessman. I felt like I was constantly judged for asking questions and expressing issues. - Food is overpriced as hell for what it is, we tried all but 1 place and they were all alright, some even just bad. It’s better to just go out in the city like we ended up doing. - No real amenities, everything has a cost just there to make you spend more money. No events or performances, they had live music 1 night during my stay. I really could go on and on. This hotel is mid at its best. If you are a normal person who wants to go on a vacation in PR, just choose anywhere else. If you want to put on a facade of being rich and powerful, this is perfect. It’s lipstick on a pig.

Reviewed on 9 Aug 2026

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5* Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
£1,261
per person
15 Sept - 22 Sept
just found
Return direct flight included
London (LON) to San Juan (SJU)
8.6/10 Excellent! (2,152 reviews)
Pretty good place to stay if it’ll be your first time in Puerto rico… still close to some places but also far enough to feel exclusive.

Reviewed on 9 Aug 2026

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
£1,469
per person
15 Sept - 22 Sept
just found
Return direct flight included
London (LON) to San Juan (SJU)
9.4/10 Exceptional! (1,795 reviews)
Good: - Nice selection of pools, they have a nice infinity hot tub on one side of the hotel, as well as a family pool. The other side has an adult only pool and hot tub. THOUGH the adult side was never super clean. Bad: - Rooms were jank, everything half worked and it looked like several fixes were just cheap patch jobs. Appliances and electronics didn’t work turn on half the time. My ocean view room I booked faced a wall and patio area. - Staff will treat you different if you aren’t some rich businessman. I felt like I was constantly judged for asking questions and expressing issues. - Food is overpriced as hell for what it is, we tried all but 1 place and they were all alright, some even just bad. It’s better to just go out in the city like we ended up doing. - No real amenities, everything has a cost just there to make you spend more money. No events or performances, they had live music 1 night during my stay. I really could go on and on. This hotel is mid at its best. If you are a normal person who wants to go on a vacation in PR, just choose anywhere else. If you want to put on a facade of being rich and powerful, this is perfect. It’s lipstick on a pig.

Reviewed on 9 Aug 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II
£1,648
per person
23 Oct - 30 Oct
found 1 day ago
Return flight included
London (LON) to San Juan (SJU)
8.6/10 Excellent! (2,188 reviews)
Horrible experience! Lazy and extremely rude staff!! Lazy cleaning staff did not clean my room 4 days!!! Extremely unprofessional!!! Reception staff extremely rude unprofessional and big liars! The reception manager is a liar! Hotel is ok, very overpriced nothing special! This is not 5 star hotel! These guys service sucks! I travel around the world! This is one of my worst experience ever!!! Terrible horrible me and my family are very disappointed won’t go back there again!!!! NEVER DONT GO

Reviewed on 8 Aug 2026

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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 £925. 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.